teknologi sediaan steril
12
1431753130778.373 DrugBank: Azithromycin (DB00207) http://www.drugbank.ca/drugs/DB00207 1/12 Show Drugs with Similar Structures Identification Name Azithromycin Accession Number DB00207 (APRD00397) Type Small Molecule Groups Approved Description Azithromycin is a semisynthetic macrolide antibiotic of the azalide class. Like other macrolide antibiotics, azithromycin inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit of the bacterial 70S ribosome. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation during the process of translation. Its effects may be bacteriostatic or bactericidal depending of the organism and the drug concentration. Its long half life, which enables once daily dosing and shorter administration durations, is a property distinct from other macrolides. Structure (http://moldb.wishartlab.com/molecules/DB00207/image.png) Synonyms Synonym Language Code (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)13((2,6Dideoxy3Cmethyl3OmethylalphaLribohexopyranosyl)oxy)2ethyl3,4,10 trihydroxy3,5,6,8,10,12,14heptamethyl11((3,4,6trideoxy3(dimethylamino)betaDxylohexopyranosyl)oxy)1oxa6 azacyclopentadecan15one Not Available Not Available Azenil Not Available Not Available Azifast Not Available Not Available Azigram Not Available Not Available Azimakrol Not Available Not Available Azithromycine French INN Azithromycinum Latin INN Azitromicina Spanish Not Available Azitromin Not Available Not Available Hemomycin Not Available Not Available Prescription Products Name Dosage Strength Route Labeller Marketing Start Marketing End Azasite solution/ drops 10 mg/mL ophthalmic Akorn, Inc. 20140514 Not Available Azasite solution 10 mg/mL ophthalmic Inspire Pharmaceuticals, Inc. 20070716 Not Available Azithromycin injection, powder, lyophilized, for solution 100 mg/mL intravenous Baxter Healthcare Corporation 19970101 Not Available Azithromycin tablet, film coated 500 mg oral Lake Erie Medical DBA Quality Care Products LLC 20020524 Not Available Azithromycin tablet, film coated 500 mg oral REMEDYREPACK INC. 20130305 Not Available Identification Taxonomy Pharmacology ADMET Pharmacoeconomics Properties Spectra References Interactions 2 Comments targets (3) enzymes (3) transporters (1) Biointeractions (8) (/drugs/DB00207/biointeractions) MOL (/structures/structures/small_molecule_drugs/DB00207.mol) SDF (/structures/structures/small_molecule_drugs/DB00207.sdf) PDB (/structures/structures/small_molecule_drugs/DB00207.pdb) SMILES (/structures/structures/small_molecule_drugs/DB00207.smiles) InChI (/structures/structures/small_molecule_drugs/DB00207.inchi) View Structure (/structures/structures/small_molecule_drugs/DB00207) Show 10 entries Search Showing 1 to 10 of 12 entries Previous 2 Next Show 10 entries Search 1
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Transcript of teknologi sediaan steril
1431753130778373 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 112
Show Drugs with Similar Structures
Identification
Name Azithromycin
Accession Number DB00207 (APRD00397)
Type Small Molecule
Groups Approved
Description Azithromycin is a semishysynthetic macrolide antibiotic of the azalide class Like other macrolide antibiotics azithromycin inhibits bacterial proteinsynthesis by binding to the 50S ribosomal subunit of the bacterial 70S ribosome Binding inhibits peptidyl transferase activity and interferes withamino acid translocation during the process of translation Its effects may be bacteriostatic or bactericidal depending of the organism and the drugconcentration Its long half life which enables once daily dosing and shorter administration durations is a property distinct from other macrolides
Structure (httpmoldbwishartlabcommoleculesDB00207imagepng)
Synonyms
Synonym Language Code
(2R3S4R5R8R10R11R12S13S14R)13shy((26shyDideoxyshy3shyCshymethylshy3shyOshymethylshyalphashyLshyriboshyhexopyranosyl)oxy)shy2shyethylshy3410shytrihydroxyshy3568101214shyheptamethylshy11shy((346shytrideoxyshy3shy(dimethylamino)shybetashyDshyxyloshyhexopyranosyl)oxy)shy1shyoxashy6shyazacyclopentadecanshy15shyone
NotAvailable
NotAvailable
Azenil NotAvailable
NotAvailable
Azifast NotAvailable
NotAvailable
Azigram NotAvailable
NotAvailable
Azimakrol NotAvailable
NotAvailable
Azithromycine French INN
Azithromycinum Latin INN
Azitromicina Spanish NotAvailable
Azitromin NotAvailable
NotAvailable
Hemomycin NotAvailable
NotAvailable
PrescriptionProducts
Name Dosage Strength Route LabellerMarketingStart
MarketingEnd
Azasite solution drops 10 mgmL ophthalmic Akorn Inc 2014shy05shy14 Not Available
Azasite solution 10 mgmL ophthalmic Inspire Pharmaceuticals Inc 2007shy07shy16 Not Available
Azithromycin injection powder lyophilizedfor solution
100 mgmL intravenous Baxter Healthcare Corporation 1997shy01shy01 Not Available
Azithromycin tablet film coated 500 mg oral Lake Erie Medical DBA Quality CareProducts LLC
2002shy05shy24 Not Available
Azithromycin tablet film coated 500 mg oral REMEDYREPACK INC 2013shy03shy05 Not Available
Identification Taxonomy Pharmacology ADMET Pharmacoeconomics Properties Spectra References Interactions 2 Comments
targets (3) enzymes (3) transporters (1) Biointeractions (8) (drugsDB00207biointeractions)
MOL (structuresstructuressmall_molecule_drugsDB00207mol) SDF (structuresstructuressmall_molecule_drugsDB00207sdf)
PDB (structuresstructuressmall_molecule_drugsDB00207pdb) SMILES (structuresstructuressmall_molecule_drugsDB00207smiles)
InChI (structuresstructuressmall_molecule_drugsDB00207inchi) View Structure (structuresstructuressmall_molecule_drugsDB00207)
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1
1431753130866963 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 212
Azithromycin tablet film coated 600 mg oral REMEDYREPACK INC 2013shy03shy05 Not Available
Azithromycin tablet film coated 250 mg oral REMEDYREPACK INC 2013shy09shy24 Not Available
Azithromycin powder for suspension 1 g oral Physicians Total Care Inc 2008shy09shy08 Not Available
Azithromycin tablet film coated 250 mg oral Cardinal Health 1996shy07shy18 Not Available
Azithromycin powder for suspension 1 g oral Greenstone LLC 1999shy02shy12 Not Available
GenericPrescriptionProducts
Name Dosage Strength Route LabellerMarketingStart
MarketingEnd
Azithromycin powder for suspension 200mg5mL
oral Teva Pharmaceuticals USA Inc 2010shy12shy17 Not Available
Azithromycin powder for suspension 100mg5mL
oral Teva Pharmaceuticals USA Inc 2010shy12shy28 Not Available
Azithromycin tablet film coated 250 mg oral Teva Pharmaceuticals USA Inc 2005shy11shy16 Not Available
Azithromycin tablet film coated 600 mg oral Teva Pharmaceuticals USA Inc 2005shy11shy16 Not Available
Azithromycin powder for suspension 100mg5mL
oral Teva Pharmaceuticals USA Inc 2008shy09shy22 Not Available
Azithromycin powder for suspension 200mg5mL
oral Teva Pharmaceuticals USA Inc 2008shy09shy22 Not Available
Azithromycin tablet film coated 500 mg oral Teva Pharmaceuticals USA Inc 2005shy11shy16 Not Available
Azithromycin tablet film coated 600 mg oral KAISER FOUNDATION HOSPITALS 2009shy09shy01 Not Available
Azithromycin injection powderlyophilized for solution
2 mgmL intravenous Hospira Inc 2009shy06shy26 Not Available
Azithromycin injection powderlyophilized for solution
100 mgmL intravenous Hospira Inc 2009shy06shy26 Not Available
Over the CounterProducts
Not Available
InternationalBrands
Name Company
Azenil Not Available
Azibiot Not Available
Azin Not Available
Azithrocin Not Available
Azitromax Not Available
Aztrin Not Available
Hemomycin Not Available
Misultina Not Available
Penalox Not Available
Sumamed Not Available
Brand mixtures Not Available
Salts NameCAS Structure Properties
Azithromycindihydrate(saltsDBSALT000882)
Notapplicable
DBSALT000882 (saltsDBSALT000882)
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1431753130903501 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 312
(httpmoldbwishartlabcommoleculesDBSALT000882imagepng)
Categories AntishyBacterial Agents (meshantishybacterialshyagents)Macrolides (meshmacrolides)
CAS number 83905shy01shy5
Weight Average 7489845 Monoisotopic 748508525778
Chemical Formula C H N O
InChI Key MQTOSJVFKKJCRPshyBICOPXKESAshyN
InChI InChI=1SC38H72N2O12c1shy15shy27shy38(1046)31(42)24(6)40(13)19shy20(2)17shy36(845)33(52shy35shy29(41)26(39(11)12)16shy21(3)48shy35)22(4)30(23(5)34(44)50shy27)51shy28shy18shy37(947shy14)32(43)25(7)49shy28h20shy333541shy4345shy46H15shy19H21shy14H3t20shy21shy22+23shy24shy25+26+27shy28+29shy30+31shy32+33shy35+36shy37shy38shym1s1
IUPAC Name (2R3S4R5R8R10R11R12S13S14R)shy11shy[(2S3R4S6R)shy4shy(dimethylamino)shy3shyhydroxyshy6shymethyloxanshy2shyyl]oxyshy2shyethylshy3410shytrihydroxyshy13shy[(2R4R5S6S)shy5shyhydroxyshy4shymethoxyshy46shydimethyloxanshy2shyyl]oxyshy3568101214shyheptamethylshy1shyoxashy6shyazacyclopentadecanshy15shyone
SMILES CC[CH]1OC(=O)[CH](C)[CH](O[CH]2C[C](C)(OC)[CH](O)[CH](C)O2)[CH](C)[CH](O[CH]2O[CH](C)C[CH]([CH]2O)N(C)C)[C](C)(O)C[CH](C)CN(C)[CH](C)[CH](O)[C]1(C)O
Taxonomy
Description This compound belongs to the class of organic compounds known as macrolides and analogues These are organic compounds containing alactone ring of at least twelve members
Kingdom Organic compounds (httpclassyfirewishartlabcomtax_nodesC0000000)
Super Class Phenylpropanoids and polyketides (httpclassyfirewishartlabcomtax_nodesC0000261)
Class Macrolides and analogues (httpclassyfirewishartlabcomtax_nodesC0000147)
Sub Class Not Available
Direct Parent Macrolides and analogues (httpclassyfirewishartlabcomtax_nodesC0000147)
Alternative Parents Amino sugars (httpclassyfirewishartlabcomtax_nodesC0001148)Oxanes (httpclassyfirewishartlabcomtax_nodesC0002012)Monosaccharides (httpclassyfirewishartlabcomtax_nodesC0001540)Tertiary alcohols (httpclassyfirewishartlabcomtax_nodesC0001670)Trialkylamines (httpclassyfirewishartlabcomtax_nodesC0002239)Secondary alcohols (httpclassyfirewishartlabcomtax_nodesC0001661)Lactones (httpclassyfirewishartlabcomtax_nodesC0000050)Carboxylic acid esters (httpclassyfirewishartlabcomtax_nodesC0001238)12shydiols (httpclassyfirewishartlabcomtax_nodesC0002467)12shyaminoalcohols (httpclassyfirewishartlabcomtax_nodesC0001897)Oxacyclic compounds (httpclassyfirewishartlabcomtax_nodesC0004140)Monocarboxylic acids and derivatives (httpclassyfirewishartlabcomtax_nodesC0001137)Dialkyl ethers (httpclassyfirewishartlabcomtax_nodesC0001167)Azacyclic compounds (httpclassyfirewishartlabcomtax_nodesC0004139)Acetals (httpclassyfirewishartlabcomtax_nodesC0001656)Hydrocarbon derivatives (httpclassyfirewishartlabcomtax_nodesC0004150)Carbonyl compounds (httpclassyfirewishartlabcomtax_nodesC0001831)
Substituents MacrolideAmino sugarDesosamineAmino saccharideOxaneMonosaccharideSaccharideTertiary alcoholTertiary aliphatic amineTertiary amineSecondary alcoholPolyolLactone
38 72 2 12
1431753130949864 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 412
Carboxylic acid ester12shydiol12shyaminoalcoholOxacycleAzacycleOrganoheterocyclic compoundMonocarboxylic acid or derivativesEtherDialkyl etherCarboxylic acid derivativeAcetalHydrocarbon derivativeOrganooxygen compoundOrganonitrogen compoundCarbonyl groupAmineAlcoholAliphatic heteromonocyclic compound
MolecularFramework
Aliphatic heteromonocyclic compounds
ExternalDescriptors
macrolide antibiotic (CHEBI2955 (httpwwwebiacukchebisearchIddochebiId=CHEBI2955))
Pharmacology
Indication For the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the specificconditions H influenzae M catarrhalis S pneumoniae C pneumoniae M pneumoniae S pyogenes S aureus S agal
Pharmacodynamics Azithromycin a semisynthetic antibiotic belonging to the macrolide subgroup of azalides is used to treat STDs due to chlamydia and gonorrheacommunityshyacquired pneumonia pelvic inflammatory disease pediatric otitis media and pharyngitis and Mycobacterium avium complex (MAC) inpatients with advanced HIV disease Similar in structure to erythromycin azithromycin reaches higher intracellular concentrations thanerythromycin increasing its efficacy and duration of action
Mechanism ofaction
Azithromycin binds to the 50S subunit of the 70S bacterial ribosomes and therefore inhibits RNAshydependent protein synthesis in bacterial cells
Absorption Bioavailability is 37 following oral administration Absorption is not affected by food Azithromycin is extensively distributed in tissues with tissueconcentrations reaching up to 50 times greater than plasma concentrations Drug becomes concentrated within macrophages andpolymorphonucleocytes giving it good activity against Chlamydia trachomatis
Volume ofdistribution
311 Lkg
Protein binding Serum protein binding is variable in the concentration range approximating human exposure decreasing from 51 at 002 microgmL to 7 at 2microgmL
Metabolism Hepatic In vitro and in vivo studies to assess the metabolism of azithromycin have not been performed
Route ofelimination
Biliary excretion of azithromycin predominantly as unchanged drug is a major route of elimination
Half life 68 hours
Clearance apparent plasma cl=630 mLmin [following single 500 mg oral and iv doses]
Toxicity Potentially serious side effects of angioedema and cholestatic jaundice were reported
Affected organisms Enteric bacteria and other eubacteria
Pathways Pathway Category SMPDB ID
Azithromycin Action Pathway Drug action SMP00247 (httpsmpdbcaviewSMP00247highlight[compounds][]=DB00207amphighlight[proteins][]=DB00207)
SNP MediatedEffects
Not Available
SNP MediatedAdverse DrugReactions
Not Available
ADMET
Predicted ADMETfeatures
Property Value Probability
Human Intestinal Absorption shy 05518
Blood Brain Barrier shy 09739
Cacoshy2 permeable shy 07578
1431753131115435 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 512
Pshyglycoprotein substrate Substrate 08765
Pshyglycoprotein inhibitor I Inhibitor 08513
Pshyglycoprotein inhibitor II Nonshyinhibitor 08893
Renal organic cation transporter Nonshyinhibitor 08753
CYP450 2C9 substrate Nonshysubstrate 08373
CYP450 2D6 substrate Nonshysubstrate 09116
CYP450 3A4 substrate Substrate 06403
CYP450 1A2 substrate Nonshyinhibitor 09295
CYP450 2C9 substrate Nonshyinhibitor 09021
CYP450 2D6 substrate Nonshyinhibitor 08904
CYP450 2C19 substrate Nonshyinhibitor 09023
CYP450 3A4 substrate Nonshyinhibitor 09533
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 09751
Ames test Non AMES toxic 09133
Carcinogenicity Nonshycarcinogens 09397
Biodegradation Not ready biodegradable 09673
Rat acute toxicity 25423 LD50 molkg Not applicable
hERG inhibition (predictor I) Weak inhibitor 09929
hERG inhibition (predictor II) Nonshyinhibitor 08555
Pharmacoeconomics
Manufacturers Pfizer chemicals div pfizer incPfizer global research developmentPliva incSandoz incTeva pharmaceuticals usaPfizer central researchApp pharmaceuticals llcGland pharma ltdHospira incPliva hrvatska dooSagent strides llcTeva parenteral medicines incPfizer inc (httpwwwpfizercom)Inspire pharmaceuticals incMylan pharmaceuticals incTeva pharmaceuticals usa incWockhardt ltd
Packagers Advanced Pharmaceutical Services IncAidarex Pharmacuticals LLC (httpwwwaidarexcom)Amerisource Health Services Corp (httpwwwamerisourcebergencom)Apotheca IncAPP Pharmaceuticals (httpwwwapppharmacom)AQ Pharmaceuticals Inc (httpwwwaqpharmaceuticalscom)AshyS Medication Solutions LLC (httpordersashysmedscom)Baxter International Inc (httpwwwbaxtercom)Cardinal Health (httpwwwcardinalcom)Catalent Pharma Solutions (httpwwwcatalentcom)Comprehensive Consultant Services IncDept Health Central PharmacyDirect Dispensing IncDispensing Solutions (httpwwwdrxdispensingcom)Diversified Healthcare Services Inc (httpwwwdhscorpcom)Eon LabsGreenstone LLC (httpwwwgreenstonellccom)HJ Harkins Co Inc (httphjharkinscompanyinccom)Hospira Inc (httpwwwhospiracom)Innoviant Pharmacy Inc (httpwwwinnoviantpharmacycom)Inspire Pharmaceuticals (httpwwwinspirepharmcom)Kaiser Foundation HospitalLake Erie Medical and Surgical SupplyLiberty Pharmaceuticals
1431753131173804 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 612
Major Pharmaceuticals (httpwwwmajorpharmaceuticalscom)Medisca Inc (httpwwwmediscacom)Murfreesboro Pharmaceutical Nursing Supply (httpwwwunitdosesupplycom)Mylan (httpwwwmylancom)Nucare Pharmaceuticals Inc (httpwwwnucarerxcom)Palmetto Pharmaceuticals Inc (httpwwwpalmettopharmcom)Patheon Inc (httpwwwpatheoncom)PDshyRx Pharmaceuticals Inc (httpwwwpdrxcom)Pfizer Inc (httpwwwpfizercom)Pharmaceutical Utilization Management Program VA IncPharmpak Inc (httpwwwpharmpakinccom)Physicians Total Care Inc (httpwwwphysicianstotalcarecom)Pliva Inc (httpwwwplivacom)Preferred Pharmaceuticals Inc (httpwwwpreferredpharmaceuticalscom)Prepackage SpecialistsPrepak Systems Inc (httpwwwprepaksyscom)Public Health Department Seattle and King County (httpwwwkingcountygovhealthserviceshealthaspx)Rebel Distributors Corp (httpwwwrebelrxcom)Redpharm DrugRemedy Repack (httpwwwremedyrepackcom)Sagent Pharmaceuticals (httpwwwsagentpharmacom)Sandoz (httpwwwsandozca)Sicor PharmaceuticalsSouthwood Pharmaceuticals (httpwwwsouthwoodhealthcarecom)Stat Rx Usa (httpstatrxusaexporteruscom)Stat Scripts LLC (httpwwwstatshyscriptscom)Strides Arcolab Limited (httpwwwstridesarcocom)Teva Pharmaceutical Industries Ltd (httpwwwtevapharmcom)Tya PharmaceuticalsUDL Laboratories (httpwwwudllabscom)US Pharmaceutical GroupWarner Chilcott Co Inc (httpirwcrxcom)Wockhardt Ltd (httpwwwwockhardtincom)
Dosage forms
Form Route Strength
Injection intravenous 500 mg10mL
Injection powder lyophilized for solution intravenous 100 mgmL
Injection powder lyophilized for solution intravenous 2 mgmL
Injection powder lyophilized for solution intravenous 500 mg5mL
Powder for suspension oral 100 mg
Powder for suspension oral 200 mg
Powder for suspension oral 1 g
Powder for suspension oral 100 mg5mL
Powder for suspension oral 1200 mg30mL
Powder for suspension oral 2 g60mL
Prices
Unit description Cost Unit
AposhyAzithromycin 250 mg Tablet 311USD tablet
Azasite 1 eye drops 4285USD ml
Azithromycin 25 gm bulk vial 756USD each
Azithromycin 200 mg5ml Suspension 15ml Bottle 3425USD bottle
Azithromycin 250 mg tablet 633USD tablet
Azithromycin 3 500 mg tablet Disp Pack 4852USD disp
Azithromycin 500 mg tablet 1587USD tablet
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1431753131233812 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 712
Azithromycin 6 250 mg tablet Disp Pack 4852USD disp
Azithromycin 600 mg tablet 1904USD tablet
Azithromycin iv 500 mg vial 1109USD each
DrugBank does not sell nor buy drugs Pricing information is supplied for informational purposes only
Patents
Country Patent Number Approved Expires (estimated)
Canada 2148071 2000shy10shy17 2015shy04shy27
Canada 2467611 2010shy03shy30 2024shy05shy18
United States 5192535 1993shy03shy09 2010shy03shy09
United States 6984403 2004shy02shy14 2024shy02shy14
Properties
State Solid
ExperimentalProperties
Property Value Source
melting point 114 degC PhysProp
water solubility slight Not Available
logP 402 MCFARLANDJW ET AL (1997)
pKa 874 (at 25 degC) MCFARLANDJW ET AL (1997)
PredictedProperties
Property Value Source
Water Solubility 0514 mgmL ALOGPS (httpwwwvcclaborglabalogps)
logP 303 ALOGPS (httpwwwvcclaborglabalogps)
logP 244 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorslogp_logd)
logS shy32 ALOGPS (httpwwwvcclaborglabalogps)
pKa (Strongest Acidic) 1243 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
pKa (Strongest Basic) 957 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Physiological Charge 2 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Hydrogen Acceptor Count 13 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Hydrogen Donor Count 5 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Polar Surface Area 18008 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopolgical_surface)
Rotatable Bond Count 7 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Refractivity 19411 m middotmol ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsrefractivity)
Polarizability 8311 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Number of Rings 3 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Bioavailability 0 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Rule of Five Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Ghose Filter Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Vebers Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
MDDRshylike Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Spectra
Mass Spec (NIST) Not Available
Spectra Not Available
References
SynthesisReference
William Heggie Zita Maria De Mouro Vaz Azevedo Mendes ldquoProcess for the preparation of azithromycinrdquo US Patent US6013778 issuedNovember 1994
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1431753131264765 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 812
US6013778 (httpswwwgooglecomtbm=ptsq=6013778amptbm=pts)
General Reference 1 Noedl H Krudsood S Chalermratana K Silachamroon U Leowattana W Tangpukdee N Looareesuwan S Miller RS Fukuda M JongsakulK Sriwichai S Rowan J Bhattacharyya H Ohrt C Knirsch C Azithromycin combination therapy with artesunate or quinine for the treatmentof uncomplicated Plasmodium falciparum malaria in adults a randomized phase 2 clinical trial in Thailand Clin Infect Dis 2006 Nov1543(10)1264shy71 Epub 2006 Oct 12 Pubmed (httpwwwncbinlmnihgovpubmed17051490)
External Links Resource Link
KEGG Compound C06838 (httpwwwgenomejpdbgetshybinwww_bgetcpdC06838)
BindingDB 50197040 (httpwwwbindingdborgbindchemsearchmarvinMolStructurejspmonomerid=50197040)
ChEBI 2955 (httpwwwebiacukchebisearchIddochebiId=2955)
ChEMBL CHEMBL529 (httpwwwebiacukchembldbindexphpcompoundinspectCHEMBL529)
Therapeutic Targets Database DNC001539 (httpbiddnusedusggroupcjttdZFTTDDRUGaspID=DNC001539)
PharmGKB PA448519 (httpwwwpharmgkborgdrugPA448519)
HET ZIT (httpwwwebiacukmsdshysrvchempdbcgishybincgiplFUNCTION=getByCodeampCODE=ZIT)
RxList httpwwwrxlistcomcgigenericzithromaxhtm (httpwwwrxlistcomcgigenericzithromaxhtm)
Drugscom httpwwwdrugscomcdiazithromycinshydropshtml (httpwwwdrugscomcdiazithromycinshydropshtml)
Wikipedia Azithromycin (httpenwikipediaorgwikiAzithromycin)
ATC Codes J01FA10J mdash ANTIINFECTIVES FOR SYSTEMIC USE (atcJJ)J01 mdash ANTIBACTERIALS FOR SYSTEMIC USE (atcJ01J01)J01F mdash MACROLIDES LINCOSAMIDES AND STREPTOGRAMINS (atcJ01FJ01F)J01FA mdash Macrolides (atcJ01FAJ01FA)
S01AA26S mdash SENSORY ORGANS (atcSS)S01 mdash OPHTHALMOLOGICALS (atcS01S01)S01A mdash ANTIINFECTIVES (atcS01AS01A)S01AA mdash Antibiotics (atcS01AAS01AA)
AHFS Codes 08121292
PDB Entries Not Available
FDA label Download (systemfda_labelsDB00207pdf1265922797) (763 KB)
MSDS Download (systemmsdsDB00207pdf1265922737) (739 KB)
Interactions
Drug Interactions Drug
Acenocoumarol(drugsDB01418)
Azithromycin may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration
Anisindione (drugsDB01125) Azithromycin may increase the anticoagulant effect of anisindione by increasing its serum concentration
Artemether (drugsDB06697) Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Cyclosporine(drugsDB00091)
The macrolide azithromycin may increase the effect of cyclosporine
Dicoumarol (drugsDB00266) Azithromycin may increase the anticoagulant effect of dicumarol by increasing its serum concentration
Disopyramide(drugsDB00280)
The macrolide azithromycin may increase the effect of disopyramide
Lovastatin (drugsDB00227) The macrolide antibiotic azithromycin may increase the serum concentration of lovastatin by decreasing its metabolismMonitor for changes in the therapeutic and adverse effects of lovastatin if azithromycin is initiated discontinued or dosechanged
Lumefantrine(drugsDB06708)
Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Vismodegib (drugsDB08828) Pshyglycoprotein inhibitors may increase the chance of adverse drug reactions
Vorinostat (drugsDB02546) Additive QTc prolongation may occur Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsadede Pointes (TdP)
Warfarin (drugsDB00682) Azithromycin may increase the anticoagulant effect of warfarin by increasing its serum concentration
Ziprasidone (drugsDB00246) Additive QTcshyprolonging effects may increase the risk of severe arrhythmias Concomitant therapy is contraindicated
Zuclopenthixol(drugsDB01624)
Additive QTc prolongation may occur Consider alternate therapy or use caution and monitor for QTc prolongation as this canlead to Torsade de Pointes (TdP)
Food Interactions Do not take Aluminum or magnesium antacids or supplements while on this medication
1431753131298898 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 912
Take on empty stomach 1 hour before or 2 hours after meals
Targets
1 23S rRNA (biodbbio_entitiesBE0004800)
Kind nucleotide
Organism Enteric bacteria and other eubacteria
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
References1 Ng LK Martin I Liu G Bryden L Mutation in 23S rRNA associated with macrolide resistance in Neisseria gonorrhoeae Antimicrob Agents Chemother 2002 Sep46(9)3020shy5
Pubmed (httpwwwncbinlmnihgovpubmed12183262)2 Jalava J Vaara M Huovinen P Mutation at the position 2058 of the 23S rRNA as a cause of macrolide resistance in Streptococcus pyogenes Ann Clin Microbiol Antimicrob
2004 May 635 Pubmed (httpwwwncbinlmnihgovpubmed15128458)3 Pereyre S Renaudin H Charron A Bebear C Bebear CM Emergence of a 23S rRNA mutation in Mycoplasma hominis associated with a loss of the intrinsic resistance to
erythromycin and azithromycin J Antimicrob Chemother 2006 Apr57(4)753shy6 Epub 2006 Feb 7 Pubmed (httpwwwncbinlmnihgovpubmed16464889)
2 50S ribosomal protein L4 (biodbbio_entitiesBE0002465)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L4 P60725 (httpwwwuniprotorguniprotP60725) Details (biodbpolypeptidesP60725)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr
22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003
Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan
30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy
24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
3 50S ribosomal protein L22 (biodbbio_entitiesBE0002464)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L22 P61177 (httpwwwuniprotorguniprotP61177) Details (biodbpolypeptidesP61177)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)
1431753131328023 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1012
2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)
3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)
4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)
5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
Enzymes
1 Cytochrome P450 2A6 (biodbbio_entitiesBE0003336)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 2A6 P11509 (httpwwwuniprotorguniprotP11509) Details (biodbpolypeptidesP11509)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
2 Cytochrome P450 3A4 (biodbbio_entitiesBE0002638)
Kind protein
Organism Human
Pharmacological action unknown
Actions substrate inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A4 P08684 (httpwwwuniprotorguniprotP08684) Details (biodbpolypeptidesP08684)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
3 Cytochrome P450 1A2 (biodbbio_entitiesBE0002433)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 1A2 P05177 (httpwwwuniprotorguniprotP05177) Details (biodbpolypeptidesP05177)
References1 Lexicomp
1431753131353312 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1112
(httpwwwcihrshyirscgcca) (httpwwwmetabolomicscentreca)
Transporters
1 Multidrug resistance protein 1 (biodbbio_entitiesBE0001032)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Multidrug resistance protein 1 P08183 (httpwwwuniprotorguniprotP08183) Details (biodbpolypeptidesP08183)
References1 Wang E Lew K Barecki M Casciano CN Clement RP Johnson WW Quantitative distinctions of active site molecular recognition by Pshyglycoprotein and cytochrome P450 3A4
Chem Res Toxicol 2001 Dec14(12)1596shy603 Pubmed (httpwwwncbinlmnihgovpubmed11743742)2 Asakura E Nakayama H Sugie M Zhao YL Nadai M Kitaichi K Shimizu A Miyoshi M Takagi K Takagi K Hasegawa T Azithromycin reverses anticancer drug resistance and
modifies hepatobiliary excretion of doxorubicin in rats Eur J Pharmacol 2004 Jan 26484(2shy3)333shy9 Pubmed (httpwwwncbinlmnihgovpubmed14744620)
Comments
Abiraterone (DB05812)4 comments bull 2 years ago
Adam Maciejewski mdash Hi PangPangGun Thanks for your questionCurrently we dont have this feature but please look at our currentpharmacoeconomics section for information regarding pricesmanufacturers packagers and dosages Thank you Adam
Denosumab (DB06643)1 comment bull 2 years ago
Glenn Pilkington mdash Tsequences you have listed are different to thepatent (WO 2013181575 A2) sequences and the heavy chain sequenceis for a hIgG1 not hIgG2
LYMshy2 (DB05788)2 comments bull a year ago
Adam Maciejewski mdash Hi Nie Lun thank you for letting us know about thisI have created a biotech entry for LYMshy2 and have merged the twodrugs Please see DB09025 Thank you
FTY 720 (DB05286)2 comments bull a year ago
Adam Maciejewski mdash Hello Daniel Himmelstein thank you for pointingthis out Indeed FTY720 is the same drug as the later approvedFingolimod I will merge the two entries into DB08868 If you have anyfurther questions or comments please dont hesitate to hellip
ALSO ON DRUGBANK
2 Comments DrugBank Login1
Share Sort by Best
Join the discussionhellip
bull Reply bull
Bmorale2 bull 3 years ago
I think the Spanish version of this should be translated to Azitromicina not as it shows as Aritromicina
bull Reply bull
Craig Knox bull 3 years agoMod gt Bmorale2
Hi thanks for the tip looks like it was a spelling error Ive corrected it 1
WHATS THIS
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Drug created on June 13 2005 0724 Updated on September 16 2013 1708
1431753133823464 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1212
(httpwwwaihealthsolutionsca) (httpgenomealbertaca) (httpgenomebcca)
(httpgenomecanadaca)
This project is supported by the Canadian Institutes of Health Research (httpwwwcihrshyirscgcca) (award 111062) Alberta Innovates shy Health Solutions(httpwwwaihealthsolutionsca) and by The Metabolomics Innovation Centre (TMIC) (httpwwwmetabolomicscentreca) a nationallyshyfunded research and corefacility that supports a wide range of cuttingshyedge metabolomic studies TMIC is funded by Genome Alberta (httpwwwgenomealbertaca) Genome British Columbia(httpwwwgenomebcca) and Genome Canada (httpwwwgenomecanadaca) a notshyforshyprofit organization that is leading Canadas national genomics strategy with$900 million in funding from the federal government
DrugBank Version 42 mdash Contact Us (httpdrugbankwcontact)
1431753130866963 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 212
Azithromycin tablet film coated 600 mg oral REMEDYREPACK INC 2013shy03shy05 Not Available
Azithromycin tablet film coated 250 mg oral REMEDYREPACK INC 2013shy09shy24 Not Available
Azithromycin powder for suspension 1 g oral Physicians Total Care Inc 2008shy09shy08 Not Available
Azithromycin tablet film coated 250 mg oral Cardinal Health 1996shy07shy18 Not Available
Azithromycin powder for suspension 1 g oral Greenstone LLC 1999shy02shy12 Not Available
GenericPrescriptionProducts
Name Dosage Strength Route LabellerMarketingStart
MarketingEnd
Azithromycin powder for suspension 200mg5mL
oral Teva Pharmaceuticals USA Inc 2010shy12shy17 Not Available
Azithromycin powder for suspension 100mg5mL
oral Teva Pharmaceuticals USA Inc 2010shy12shy28 Not Available
Azithromycin tablet film coated 250 mg oral Teva Pharmaceuticals USA Inc 2005shy11shy16 Not Available
Azithromycin tablet film coated 600 mg oral Teva Pharmaceuticals USA Inc 2005shy11shy16 Not Available
Azithromycin powder for suspension 100mg5mL
oral Teva Pharmaceuticals USA Inc 2008shy09shy22 Not Available
Azithromycin powder for suspension 200mg5mL
oral Teva Pharmaceuticals USA Inc 2008shy09shy22 Not Available
Azithromycin tablet film coated 500 mg oral Teva Pharmaceuticals USA Inc 2005shy11shy16 Not Available
Azithromycin tablet film coated 600 mg oral KAISER FOUNDATION HOSPITALS 2009shy09shy01 Not Available
Azithromycin injection powderlyophilized for solution
2 mgmL intravenous Hospira Inc 2009shy06shy26 Not Available
Azithromycin injection powderlyophilized for solution
100 mgmL intravenous Hospira Inc 2009shy06shy26 Not Available
Over the CounterProducts
Not Available
InternationalBrands
Name Company
Azenil Not Available
Azibiot Not Available
Azin Not Available
Azithrocin Not Available
Azitromax Not Available
Aztrin Not Available
Hemomycin Not Available
Misultina Not Available
Penalox Not Available
Sumamed Not Available
Brand mixtures Not Available
Salts NameCAS Structure Properties
Azithromycindihydrate(saltsDBSALT000882)
Notapplicable
DBSALT000882 (saltsDBSALT000882)
Showing 1 to 10 of 37 entries Previous 2 3 4 Next
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1
1431753130903501 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 312
(httpmoldbwishartlabcommoleculesDBSALT000882imagepng)
Categories AntishyBacterial Agents (meshantishybacterialshyagents)Macrolides (meshmacrolides)
CAS number 83905shy01shy5
Weight Average 7489845 Monoisotopic 748508525778
Chemical Formula C H N O
InChI Key MQTOSJVFKKJCRPshyBICOPXKESAshyN
InChI InChI=1SC38H72N2O12c1shy15shy27shy38(1046)31(42)24(6)40(13)19shy20(2)17shy36(845)33(52shy35shy29(41)26(39(11)12)16shy21(3)48shy35)22(4)30(23(5)34(44)50shy27)51shy28shy18shy37(947shy14)32(43)25(7)49shy28h20shy333541shy4345shy46H15shy19H21shy14H3t20shy21shy22+23shy24shy25+26+27shy28+29shy30+31shy32+33shy35+36shy37shy38shym1s1
IUPAC Name (2R3S4R5R8R10R11R12S13S14R)shy11shy[(2S3R4S6R)shy4shy(dimethylamino)shy3shyhydroxyshy6shymethyloxanshy2shyyl]oxyshy2shyethylshy3410shytrihydroxyshy13shy[(2R4R5S6S)shy5shyhydroxyshy4shymethoxyshy46shydimethyloxanshy2shyyl]oxyshy3568101214shyheptamethylshy1shyoxashy6shyazacyclopentadecanshy15shyone
SMILES CC[CH]1OC(=O)[CH](C)[CH](O[CH]2C[C](C)(OC)[CH](O)[CH](C)O2)[CH](C)[CH](O[CH]2O[CH](C)C[CH]([CH]2O)N(C)C)[C](C)(O)C[CH](C)CN(C)[CH](C)[CH](O)[C]1(C)O
Taxonomy
Description This compound belongs to the class of organic compounds known as macrolides and analogues These are organic compounds containing alactone ring of at least twelve members
Kingdom Organic compounds (httpclassyfirewishartlabcomtax_nodesC0000000)
Super Class Phenylpropanoids and polyketides (httpclassyfirewishartlabcomtax_nodesC0000261)
Class Macrolides and analogues (httpclassyfirewishartlabcomtax_nodesC0000147)
Sub Class Not Available
Direct Parent Macrolides and analogues (httpclassyfirewishartlabcomtax_nodesC0000147)
Alternative Parents Amino sugars (httpclassyfirewishartlabcomtax_nodesC0001148)Oxanes (httpclassyfirewishartlabcomtax_nodesC0002012)Monosaccharides (httpclassyfirewishartlabcomtax_nodesC0001540)Tertiary alcohols (httpclassyfirewishartlabcomtax_nodesC0001670)Trialkylamines (httpclassyfirewishartlabcomtax_nodesC0002239)Secondary alcohols (httpclassyfirewishartlabcomtax_nodesC0001661)Lactones (httpclassyfirewishartlabcomtax_nodesC0000050)Carboxylic acid esters (httpclassyfirewishartlabcomtax_nodesC0001238)12shydiols (httpclassyfirewishartlabcomtax_nodesC0002467)12shyaminoalcohols (httpclassyfirewishartlabcomtax_nodesC0001897)Oxacyclic compounds (httpclassyfirewishartlabcomtax_nodesC0004140)Monocarboxylic acids and derivatives (httpclassyfirewishartlabcomtax_nodesC0001137)Dialkyl ethers (httpclassyfirewishartlabcomtax_nodesC0001167)Azacyclic compounds (httpclassyfirewishartlabcomtax_nodesC0004139)Acetals (httpclassyfirewishartlabcomtax_nodesC0001656)Hydrocarbon derivatives (httpclassyfirewishartlabcomtax_nodesC0004150)Carbonyl compounds (httpclassyfirewishartlabcomtax_nodesC0001831)
Substituents MacrolideAmino sugarDesosamineAmino saccharideOxaneMonosaccharideSaccharideTertiary alcoholTertiary aliphatic amineTertiary amineSecondary alcoholPolyolLactone
38 72 2 12
1431753130949864 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 412
Carboxylic acid ester12shydiol12shyaminoalcoholOxacycleAzacycleOrganoheterocyclic compoundMonocarboxylic acid or derivativesEtherDialkyl etherCarboxylic acid derivativeAcetalHydrocarbon derivativeOrganooxygen compoundOrganonitrogen compoundCarbonyl groupAmineAlcoholAliphatic heteromonocyclic compound
MolecularFramework
Aliphatic heteromonocyclic compounds
ExternalDescriptors
macrolide antibiotic (CHEBI2955 (httpwwwebiacukchebisearchIddochebiId=CHEBI2955))
Pharmacology
Indication For the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the specificconditions H influenzae M catarrhalis S pneumoniae C pneumoniae M pneumoniae S pyogenes S aureus S agal
Pharmacodynamics Azithromycin a semisynthetic antibiotic belonging to the macrolide subgroup of azalides is used to treat STDs due to chlamydia and gonorrheacommunityshyacquired pneumonia pelvic inflammatory disease pediatric otitis media and pharyngitis and Mycobacterium avium complex (MAC) inpatients with advanced HIV disease Similar in structure to erythromycin azithromycin reaches higher intracellular concentrations thanerythromycin increasing its efficacy and duration of action
Mechanism ofaction
Azithromycin binds to the 50S subunit of the 70S bacterial ribosomes and therefore inhibits RNAshydependent protein synthesis in bacterial cells
Absorption Bioavailability is 37 following oral administration Absorption is not affected by food Azithromycin is extensively distributed in tissues with tissueconcentrations reaching up to 50 times greater than plasma concentrations Drug becomes concentrated within macrophages andpolymorphonucleocytes giving it good activity against Chlamydia trachomatis
Volume ofdistribution
311 Lkg
Protein binding Serum protein binding is variable in the concentration range approximating human exposure decreasing from 51 at 002 microgmL to 7 at 2microgmL
Metabolism Hepatic In vitro and in vivo studies to assess the metabolism of azithromycin have not been performed
Route ofelimination
Biliary excretion of azithromycin predominantly as unchanged drug is a major route of elimination
Half life 68 hours
Clearance apparent plasma cl=630 mLmin [following single 500 mg oral and iv doses]
Toxicity Potentially serious side effects of angioedema and cholestatic jaundice were reported
Affected organisms Enteric bacteria and other eubacteria
Pathways Pathway Category SMPDB ID
Azithromycin Action Pathway Drug action SMP00247 (httpsmpdbcaviewSMP00247highlight[compounds][]=DB00207amphighlight[proteins][]=DB00207)
SNP MediatedEffects
Not Available
SNP MediatedAdverse DrugReactions
Not Available
ADMET
Predicted ADMETfeatures
Property Value Probability
Human Intestinal Absorption shy 05518
Blood Brain Barrier shy 09739
Cacoshy2 permeable shy 07578
1431753131115435 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 512
Pshyglycoprotein substrate Substrate 08765
Pshyglycoprotein inhibitor I Inhibitor 08513
Pshyglycoprotein inhibitor II Nonshyinhibitor 08893
Renal organic cation transporter Nonshyinhibitor 08753
CYP450 2C9 substrate Nonshysubstrate 08373
CYP450 2D6 substrate Nonshysubstrate 09116
CYP450 3A4 substrate Substrate 06403
CYP450 1A2 substrate Nonshyinhibitor 09295
CYP450 2C9 substrate Nonshyinhibitor 09021
CYP450 2D6 substrate Nonshyinhibitor 08904
CYP450 2C19 substrate Nonshyinhibitor 09023
CYP450 3A4 substrate Nonshyinhibitor 09533
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 09751
Ames test Non AMES toxic 09133
Carcinogenicity Nonshycarcinogens 09397
Biodegradation Not ready biodegradable 09673
Rat acute toxicity 25423 LD50 molkg Not applicable
hERG inhibition (predictor I) Weak inhibitor 09929
hERG inhibition (predictor II) Nonshyinhibitor 08555
Pharmacoeconomics
Manufacturers Pfizer chemicals div pfizer incPfizer global research developmentPliva incSandoz incTeva pharmaceuticals usaPfizer central researchApp pharmaceuticals llcGland pharma ltdHospira incPliva hrvatska dooSagent strides llcTeva parenteral medicines incPfizer inc (httpwwwpfizercom)Inspire pharmaceuticals incMylan pharmaceuticals incTeva pharmaceuticals usa incWockhardt ltd
Packagers Advanced Pharmaceutical Services IncAidarex Pharmacuticals LLC (httpwwwaidarexcom)Amerisource Health Services Corp (httpwwwamerisourcebergencom)Apotheca IncAPP Pharmaceuticals (httpwwwapppharmacom)AQ Pharmaceuticals Inc (httpwwwaqpharmaceuticalscom)AshyS Medication Solutions LLC (httpordersashysmedscom)Baxter International Inc (httpwwwbaxtercom)Cardinal Health (httpwwwcardinalcom)Catalent Pharma Solutions (httpwwwcatalentcom)Comprehensive Consultant Services IncDept Health Central PharmacyDirect Dispensing IncDispensing Solutions (httpwwwdrxdispensingcom)Diversified Healthcare Services Inc (httpwwwdhscorpcom)Eon LabsGreenstone LLC (httpwwwgreenstonellccom)HJ Harkins Co Inc (httphjharkinscompanyinccom)Hospira Inc (httpwwwhospiracom)Innoviant Pharmacy Inc (httpwwwinnoviantpharmacycom)Inspire Pharmaceuticals (httpwwwinspirepharmcom)Kaiser Foundation HospitalLake Erie Medical and Surgical SupplyLiberty Pharmaceuticals
1431753131173804 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 612
Major Pharmaceuticals (httpwwwmajorpharmaceuticalscom)Medisca Inc (httpwwwmediscacom)Murfreesboro Pharmaceutical Nursing Supply (httpwwwunitdosesupplycom)Mylan (httpwwwmylancom)Nucare Pharmaceuticals Inc (httpwwwnucarerxcom)Palmetto Pharmaceuticals Inc (httpwwwpalmettopharmcom)Patheon Inc (httpwwwpatheoncom)PDshyRx Pharmaceuticals Inc (httpwwwpdrxcom)Pfizer Inc (httpwwwpfizercom)Pharmaceutical Utilization Management Program VA IncPharmpak Inc (httpwwwpharmpakinccom)Physicians Total Care Inc (httpwwwphysicianstotalcarecom)Pliva Inc (httpwwwplivacom)Preferred Pharmaceuticals Inc (httpwwwpreferredpharmaceuticalscom)Prepackage SpecialistsPrepak Systems Inc (httpwwwprepaksyscom)Public Health Department Seattle and King County (httpwwwkingcountygovhealthserviceshealthaspx)Rebel Distributors Corp (httpwwwrebelrxcom)Redpharm DrugRemedy Repack (httpwwwremedyrepackcom)Sagent Pharmaceuticals (httpwwwsagentpharmacom)Sandoz (httpwwwsandozca)Sicor PharmaceuticalsSouthwood Pharmaceuticals (httpwwwsouthwoodhealthcarecom)Stat Rx Usa (httpstatrxusaexporteruscom)Stat Scripts LLC (httpwwwstatshyscriptscom)Strides Arcolab Limited (httpwwwstridesarcocom)Teva Pharmaceutical Industries Ltd (httpwwwtevapharmcom)Tya PharmaceuticalsUDL Laboratories (httpwwwudllabscom)US Pharmaceutical GroupWarner Chilcott Co Inc (httpirwcrxcom)Wockhardt Ltd (httpwwwwockhardtincom)
Dosage forms
Form Route Strength
Injection intravenous 500 mg10mL
Injection powder lyophilized for solution intravenous 100 mgmL
Injection powder lyophilized for solution intravenous 2 mgmL
Injection powder lyophilized for solution intravenous 500 mg5mL
Powder for suspension oral 100 mg
Powder for suspension oral 200 mg
Powder for suspension oral 1 g
Powder for suspension oral 100 mg5mL
Powder for suspension oral 1200 mg30mL
Powder for suspension oral 2 g60mL
Prices
Unit description Cost Unit
AposhyAzithromycin 250 mg Tablet 311USD tablet
Azasite 1 eye drops 4285USD ml
Azithromycin 25 gm bulk vial 756USD each
Azithromycin 200 mg5ml Suspension 15ml Bottle 3425USD bottle
Azithromycin 250 mg tablet 633USD tablet
Azithromycin 3 500 mg tablet Disp Pack 4852USD disp
Azithromycin 500 mg tablet 1587USD tablet
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1
1431753131233812 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 712
Azithromycin 6 250 mg tablet Disp Pack 4852USD disp
Azithromycin 600 mg tablet 1904USD tablet
Azithromycin iv 500 mg vial 1109USD each
DrugBank does not sell nor buy drugs Pricing information is supplied for informational purposes only
Patents
Country Patent Number Approved Expires (estimated)
Canada 2148071 2000shy10shy17 2015shy04shy27
Canada 2467611 2010shy03shy30 2024shy05shy18
United States 5192535 1993shy03shy09 2010shy03shy09
United States 6984403 2004shy02shy14 2024shy02shy14
Properties
State Solid
ExperimentalProperties
Property Value Source
melting point 114 degC PhysProp
water solubility slight Not Available
logP 402 MCFARLANDJW ET AL (1997)
pKa 874 (at 25 degC) MCFARLANDJW ET AL (1997)
PredictedProperties
Property Value Source
Water Solubility 0514 mgmL ALOGPS (httpwwwvcclaborglabalogps)
logP 303 ALOGPS (httpwwwvcclaborglabalogps)
logP 244 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorslogp_logd)
logS shy32 ALOGPS (httpwwwvcclaborglabalogps)
pKa (Strongest Acidic) 1243 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
pKa (Strongest Basic) 957 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Physiological Charge 2 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Hydrogen Acceptor Count 13 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Hydrogen Donor Count 5 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Polar Surface Area 18008 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopolgical_surface)
Rotatable Bond Count 7 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Refractivity 19411 m middotmol ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsrefractivity)
Polarizability 8311 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Number of Rings 3 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Bioavailability 0 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Rule of Five Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Ghose Filter Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Vebers Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
MDDRshylike Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Spectra
Mass Spec (NIST) Not Available
Spectra Not Available
References
SynthesisReference
William Heggie Zita Maria De Mouro Vaz Azevedo Mendes ldquoProcess for the preparation of azithromycinrdquo US Patent US6013778 issuedNovember 1994
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1431753131264765 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 812
US6013778 (httpswwwgooglecomtbm=ptsq=6013778amptbm=pts)
General Reference 1 Noedl H Krudsood S Chalermratana K Silachamroon U Leowattana W Tangpukdee N Looareesuwan S Miller RS Fukuda M JongsakulK Sriwichai S Rowan J Bhattacharyya H Ohrt C Knirsch C Azithromycin combination therapy with artesunate or quinine for the treatmentof uncomplicated Plasmodium falciparum malaria in adults a randomized phase 2 clinical trial in Thailand Clin Infect Dis 2006 Nov1543(10)1264shy71 Epub 2006 Oct 12 Pubmed (httpwwwncbinlmnihgovpubmed17051490)
External Links Resource Link
KEGG Compound C06838 (httpwwwgenomejpdbgetshybinwww_bgetcpdC06838)
BindingDB 50197040 (httpwwwbindingdborgbindchemsearchmarvinMolStructurejspmonomerid=50197040)
ChEBI 2955 (httpwwwebiacukchebisearchIddochebiId=2955)
ChEMBL CHEMBL529 (httpwwwebiacukchembldbindexphpcompoundinspectCHEMBL529)
Therapeutic Targets Database DNC001539 (httpbiddnusedusggroupcjttdZFTTDDRUGaspID=DNC001539)
PharmGKB PA448519 (httpwwwpharmgkborgdrugPA448519)
HET ZIT (httpwwwebiacukmsdshysrvchempdbcgishybincgiplFUNCTION=getByCodeampCODE=ZIT)
RxList httpwwwrxlistcomcgigenericzithromaxhtm (httpwwwrxlistcomcgigenericzithromaxhtm)
Drugscom httpwwwdrugscomcdiazithromycinshydropshtml (httpwwwdrugscomcdiazithromycinshydropshtml)
Wikipedia Azithromycin (httpenwikipediaorgwikiAzithromycin)
ATC Codes J01FA10J mdash ANTIINFECTIVES FOR SYSTEMIC USE (atcJJ)J01 mdash ANTIBACTERIALS FOR SYSTEMIC USE (atcJ01J01)J01F mdash MACROLIDES LINCOSAMIDES AND STREPTOGRAMINS (atcJ01FJ01F)J01FA mdash Macrolides (atcJ01FAJ01FA)
S01AA26S mdash SENSORY ORGANS (atcSS)S01 mdash OPHTHALMOLOGICALS (atcS01S01)S01A mdash ANTIINFECTIVES (atcS01AS01A)S01AA mdash Antibiotics (atcS01AAS01AA)
AHFS Codes 08121292
PDB Entries Not Available
FDA label Download (systemfda_labelsDB00207pdf1265922797) (763 KB)
MSDS Download (systemmsdsDB00207pdf1265922737) (739 KB)
Interactions
Drug Interactions Drug
Acenocoumarol(drugsDB01418)
Azithromycin may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration
Anisindione (drugsDB01125) Azithromycin may increase the anticoagulant effect of anisindione by increasing its serum concentration
Artemether (drugsDB06697) Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Cyclosporine(drugsDB00091)
The macrolide azithromycin may increase the effect of cyclosporine
Dicoumarol (drugsDB00266) Azithromycin may increase the anticoagulant effect of dicumarol by increasing its serum concentration
Disopyramide(drugsDB00280)
The macrolide azithromycin may increase the effect of disopyramide
Lovastatin (drugsDB00227) The macrolide antibiotic azithromycin may increase the serum concentration of lovastatin by decreasing its metabolismMonitor for changes in the therapeutic and adverse effects of lovastatin if azithromycin is initiated discontinued or dosechanged
Lumefantrine(drugsDB06708)
Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Vismodegib (drugsDB08828) Pshyglycoprotein inhibitors may increase the chance of adverse drug reactions
Vorinostat (drugsDB02546) Additive QTc prolongation may occur Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsadede Pointes (TdP)
Warfarin (drugsDB00682) Azithromycin may increase the anticoagulant effect of warfarin by increasing its serum concentration
Ziprasidone (drugsDB00246) Additive QTcshyprolonging effects may increase the risk of severe arrhythmias Concomitant therapy is contraindicated
Zuclopenthixol(drugsDB01624)
Additive QTc prolongation may occur Consider alternate therapy or use caution and monitor for QTc prolongation as this canlead to Torsade de Pointes (TdP)
Food Interactions Do not take Aluminum or magnesium antacids or supplements while on this medication
1431753131298898 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 912
Take on empty stomach 1 hour before or 2 hours after meals
Targets
1 23S rRNA (biodbbio_entitiesBE0004800)
Kind nucleotide
Organism Enteric bacteria and other eubacteria
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
References1 Ng LK Martin I Liu G Bryden L Mutation in 23S rRNA associated with macrolide resistance in Neisseria gonorrhoeae Antimicrob Agents Chemother 2002 Sep46(9)3020shy5
Pubmed (httpwwwncbinlmnihgovpubmed12183262)2 Jalava J Vaara M Huovinen P Mutation at the position 2058 of the 23S rRNA as a cause of macrolide resistance in Streptococcus pyogenes Ann Clin Microbiol Antimicrob
2004 May 635 Pubmed (httpwwwncbinlmnihgovpubmed15128458)3 Pereyre S Renaudin H Charron A Bebear C Bebear CM Emergence of a 23S rRNA mutation in Mycoplasma hominis associated with a loss of the intrinsic resistance to
erythromycin and azithromycin J Antimicrob Chemother 2006 Apr57(4)753shy6 Epub 2006 Feb 7 Pubmed (httpwwwncbinlmnihgovpubmed16464889)
2 50S ribosomal protein L4 (biodbbio_entitiesBE0002465)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L4 P60725 (httpwwwuniprotorguniprotP60725) Details (biodbpolypeptidesP60725)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr
22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003
Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan
30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy
24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
3 50S ribosomal protein L22 (biodbbio_entitiesBE0002464)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L22 P61177 (httpwwwuniprotorguniprotP61177) Details (biodbpolypeptidesP61177)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)
1431753131328023 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1012
2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)
3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)
4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)
5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
Enzymes
1 Cytochrome P450 2A6 (biodbbio_entitiesBE0003336)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 2A6 P11509 (httpwwwuniprotorguniprotP11509) Details (biodbpolypeptidesP11509)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
2 Cytochrome P450 3A4 (biodbbio_entitiesBE0002638)
Kind protein
Organism Human
Pharmacological action unknown
Actions substrate inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A4 P08684 (httpwwwuniprotorguniprotP08684) Details (biodbpolypeptidesP08684)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
3 Cytochrome P450 1A2 (biodbbio_entitiesBE0002433)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 1A2 P05177 (httpwwwuniprotorguniprotP05177) Details (biodbpolypeptidesP05177)
References1 Lexicomp
1431753131353312 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1112
(httpwwwcihrshyirscgcca) (httpwwwmetabolomicscentreca)
Transporters
1 Multidrug resistance protein 1 (biodbbio_entitiesBE0001032)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Multidrug resistance protein 1 P08183 (httpwwwuniprotorguniprotP08183) Details (biodbpolypeptidesP08183)
References1 Wang E Lew K Barecki M Casciano CN Clement RP Johnson WW Quantitative distinctions of active site molecular recognition by Pshyglycoprotein and cytochrome P450 3A4
Chem Res Toxicol 2001 Dec14(12)1596shy603 Pubmed (httpwwwncbinlmnihgovpubmed11743742)2 Asakura E Nakayama H Sugie M Zhao YL Nadai M Kitaichi K Shimizu A Miyoshi M Takagi K Takagi K Hasegawa T Azithromycin reverses anticancer drug resistance and
modifies hepatobiliary excretion of doxorubicin in rats Eur J Pharmacol 2004 Jan 26484(2shy3)333shy9 Pubmed (httpwwwncbinlmnihgovpubmed14744620)
Comments
Abiraterone (DB05812)4 comments bull 2 years ago
Adam Maciejewski mdash Hi PangPangGun Thanks for your questionCurrently we dont have this feature but please look at our currentpharmacoeconomics section for information regarding pricesmanufacturers packagers and dosages Thank you Adam
Denosumab (DB06643)1 comment bull 2 years ago
Glenn Pilkington mdash Tsequences you have listed are different to thepatent (WO 2013181575 A2) sequences and the heavy chain sequenceis for a hIgG1 not hIgG2
LYMshy2 (DB05788)2 comments bull a year ago
Adam Maciejewski mdash Hi Nie Lun thank you for letting us know about thisI have created a biotech entry for LYMshy2 and have merged the twodrugs Please see DB09025 Thank you
FTY 720 (DB05286)2 comments bull a year ago
Adam Maciejewski mdash Hello Daniel Himmelstein thank you for pointingthis out Indeed FTY720 is the same drug as the later approvedFingolimod I will merge the two entries into DB08868 If you have anyfurther questions or comments please dont hesitate to hellip
ALSO ON DRUGBANK
2 Comments DrugBank Login1
Share Sort by Best
Join the discussionhellip
bull Reply bull
Bmorale2 bull 3 years ago
I think the Spanish version of this should be translated to Azitromicina not as it shows as Aritromicina
bull Reply bull
Craig Knox bull 3 years agoMod gt Bmorale2
Hi thanks for the tip looks like it was a spelling error Ive corrected it 1
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Drug created on June 13 2005 0724 Updated on September 16 2013 1708
1431753133823464 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1212
(httpwwwaihealthsolutionsca) (httpgenomealbertaca) (httpgenomebcca)
(httpgenomecanadaca)
This project is supported by the Canadian Institutes of Health Research (httpwwwcihrshyirscgcca) (award 111062) Alberta Innovates shy Health Solutions(httpwwwaihealthsolutionsca) and by The Metabolomics Innovation Centre (TMIC) (httpwwwmetabolomicscentreca) a nationallyshyfunded research and corefacility that supports a wide range of cuttingshyedge metabolomic studies TMIC is funded by Genome Alberta (httpwwwgenomealbertaca) Genome British Columbia(httpwwwgenomebcca) and Genome Canada (httpwwwgenomecanadaca) a notshyforshyprofit organization that is leading Canadas national genomics strategy with$900 million in funding from the federal government
DrugBank Version 42 mdash Contact Us (httpdrugbankwcontact)
1431753130903501 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 312
(httpmoldbwishartlabcommoleculesDBSALT000882imagepng)
Categories AntishyBacterial Agents (meshantishybacterialshyagents)Macrolides (meshmacrolides)
CAS number 83905shy01shy5
Weight Average 7489845 Monoisotopic 748508525778
Chemical Formula C H N O
InChI Key MQTOSJVFKKJCRPshyBICOPXKESAshyN
InChI InChI=1SC38H72N2O12c1shy15shy27shy38(1046)31(42)24(6)40(13)19shy20(2)17shy36(845)33(52shy35shy29(41)26(39(11)12)16shy21(3)48shy35)22(4)30(23(5)34(44)50shy27)51shy28shy18shy37(947shy14)32(43)25(7)49shy28h20shy333541shy4345shy46H15shy19H21shy14H3t20shy21shy22+23shy24shy25+26+27shy28+29shy30+31shy32+33shy35+36shy37shy38shym1s1
IUPAC Name (2R3S4R5R8R10R11R12S13S14R)shy11shy[(2S3R4S6R)shy4shy(dimethylamino)shy3shyhydroxyshy6shymethyloxanshy2shyyl]oxyshy2shyethylshy3410shytrihydroxyshy13shy[(2R4R5S6S)shy5shyhydroxyshy4shymethoxyshy46shydimethyloxanshy2shyyl]oxyshy3568101214shyheptamethylshy1shyoxashy6shyazacyclopentadecanshy15shyone
SMILES CC[CH]1OC(=O)[CH](C)[CH](O[CH]2C[C](C)(OC)[CH](O)[CH](C)O2)[CH](C)[CH](O[CH]2O[CH](C)C[CH]([CH]2O)N(C)C)[C](C)(O)C[CH](C)CN(C)[CH](C)[CH](O)[C]1(C)O
Taxonomy
Description This compound belongs to the class of organic compounds known as macrolides and analogues These are organic compounds containing alactone ring of at least twelve members
Kingdom Organic compounds (httpclassyfirewishartlabcomtax_nodesC0000000)
Super Class Phenylpropanoids and polyketides (httpclassyfirewishartlabcomtax_nodesC0000261)
Class Macrolides and analogues (httpclassyfirewishartlabcomtax_nodesC0000147)
Sub Class Not Available
Direct Parent Macrolides and analogues (httpclassyfirewishartlabcomtax_nodesC0000147)
Alternative Parents Amino sugars (httpclassyfirewishartlabcomtax_nodesC0001148)Oxanes (httpclassyfirewishartlabcomtax_nodesC0002012)Monosaccharides (httpclassyfirewishartlabcomtax_nodesC0001540)Tertiary alcohols (httpclassyfirewishartlabcomtax_nodesC0001670)Trialkylamines (httpclassyfirewishartlabcomtax_nodesC0002239)Secondary alcohols (httpclassyfirewishartlabcomtax_nodesC0001661)Lactones (httpclassyfirewishartlabcomtax_nodesC0000050)Carboxylic acid esters (httpclassyfirewishartlabcomtax_nodesC0001238)12shydiols (httpclassyfirewishartlabcomtax_nodesC0002467)12shyaminoalcohols (httpclassyfirewishartlabcomtax_nodesC0001897)Oxacyclic compounds (httpclassyfirewishartlabcomtax_nodesC0004140)Monocarboxylic acids and derivatives (httpclassyfirewishartlabcomtax_nodesC0001137)Dialkyl ethers (httpclassyfirewishartlabcomtax_nodesC0001167)Azacyclic compounds (httpclassyfirewishartlabcomtax_nodesC0004139)Acetals (httpclassyfirewishartlabcomtax_nodesC0001656)Hydrocarbon derivatives (httpclassyfirewishartlabcomtax_nodesC0004150)Carbonyl compounds (httpclassyfirewishartlabcomtax_nodesC0001831)
Substituents MacrolideAmino sugarDesosamineAmino saccharideOxaneMonosaccharideSaccharideTertiary alcoholTertiary aliphatic amineTertiary amineSecondary alcoholPolyolLactone
38 72 2 12
1431753130949864 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 412
Carboxylic acid ester12shydiol12shyaminoalcoholOxacycleAzacycleOrganoheterocyclic compoundMonocarboxylic acid or derivativesEtherDialkyl etherCarboxylic acid derivativeAcetalHydrocarbon derivativeOrganooxygen compoundOrganonitrogen compoundCarbonyl groupAmineAlcoholAliphatic heteromonocyclic compound
MolecularFramework
Aliphatic heteromonocyclic compounds
ExternalDescriptors
macrolide antibiotic (CHEBI2955 (httpwwwebiacukchebisearchIddochebiId=CHEBI2955))
Pharmacology
Indication For the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the specificconditions H influenzae M catarrhalis S pneumoniae C pneumoniae M pneumoniae S pyogenes S aureus S agal
Pharmacodynamics Azithromycin a semisynthetic antibiotic belonging to the macrolide subgroup of azalides is used to treat STDs due to chlamydia and gonorrheacommunityshyacquired pneumonia pelvic inflammatory disease pediatric otitis media and pharyngitis and Mycobacterium avium complex (MAC) inpatients with advanced HIV disease Similar in structure to erythromycin azithromycin reaches higher intracellular concentrations thanerythromycin increasing its efficacy and duration of action
Mechanism ofaction
Azithromycin binds to the 50S subunit of the 70S bacterial ribosomes and therefore inhibits RNAshydependent protein synthesis in bacterial cells
Absorption Bioavailability is 37 following oral administration Absorption is not affected by food Azithromycin is extensively distributed in tissues with tissueconcentrations reaching up to 50 times greater than plasma concentrations Drug becomes concentrated within macrophages andpolymorphonucleocytes giving it good activity against Chlamydia trachomatis
Volume ofdistribution
311 Lkg
Protein binding Serum protein binding is variable in the concentration range approximating human exposure decreasing from 51 at 002 microgmL to 7 at 2microgmL
Metabolism Hepatic In vitro and in vivo studies to assess the metabolism of azithromycin have not been performed
Route ofelimination
Biliary excretion of azithromycin predominantly as unchanged drug is a major route of elimination
Half life 68 hours
Clearance apparent plasma cl=630 mLmin [following single 500 mg oral and iv doses]
Toxicity Potentially serious side effects of angioedema and cholestatic jaundice were reported
Affected organisms Enteric bacteria and other eubacteria
Pathways Pathway Category SMPDB ID
Azithromycin Action Pathway Drug action SMP00247 (httpsmpdbcaviewSMP00247highlight[compounds][]=DB00207amphighlight[proteins][]=DB00207)
SNP MediatedEffects
Not Available
SNP MediatedAdverse DrugReactions
Not Available
ADMET
Predicted ADMETfeatures
Property Value Probability
Human Intestinal Absorption shy 05518
Blood Brain Barrier shy 09739
Cacoshy2 permeable shy 07578
1431753131115435 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 512
Pshyglycoprotein substrate Substrate 08765
Pshyglycoprotein inhibitor I Inhibitor 08513
Pshyglycoprotein inhibitor II Nonshyinhibitor 08893
Renal organic cation transporter Nonshyinhibitor 08753
CYP450 2C9 substrate Nonshysubstrate 08373
CYP450 2D6 substrate Nonshysubstrate 09116
CYP450 3A4 substrate Substrate 06403
CYP450 1A2 substrate Nonshyinhibitor 09295
CYP450 2C9 substrate Nonshyinhibitor 09021
CYP450 2D6 substrate Nonshyinhibitor 08904
CYP450 2C19 substrate Nonshyinhibitor 09023
CYP450 3A4 substrate Nonshyinhibitor 09533
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 09751
Ames test Non AMES toxic 09133
Carcinogenicity Nonshycarcinogens 09397
Biodegradation Not ready biodegradable 09673
Rat acute toxicity 25423 LD50 molkg Not applicable
hERG inhibition (predictor I) Weak inhibitor 09929
hERG inhibition (predictor II) Nonshyinhibitor 08555
Pharmacoeconomics
Manufacturers Pfizer chemicals div pfizer incPfizer global research developmentPliva incSandoz incTeva pharmaceuticals usaPfizer central researchApp pharmaceuticals llcGland pharma ltdHospira incPliva hrvatska dooSagent strides llcTeva parenteral medicines incPfizer inc (httpwwwpfizercom)Inspire pharmaceuticals incMylan pharmaceuticals incTeva pharmaceuticals usa incWockhardt ltd
Packagers Advanced Pharmaceutical Services IncAidarex Pharmacuticals LLC (httpwwwaidarexcom)Amerisource Health Services Corp (httpwwwamerisourcebergencom)Apotheca IncAPP Pharmaceuticals (httpwwwapppharmacom)AQ Pharmaceuticals Inc (httpwwwaqpharmaceuticalscom)AshyS Medication Solutions LLC (httpordersashysmedscom)Baxter International Inc (httpwwwbaxtercom)Cardinal Health (httpwwwcardinalcom)Catalent Pharma Solutions (httpwwwcatalentcom)Comprehensive Consultant Services IncDept Health Central PharmacyDirect Dispensing IncDispensing Solutions (httpwwwdrxdispensingcom)Diversified Healthcare Services Inc (httpwwwdhscorpcom)Eon LabsGreenstone LLC (httpwwwgreenstonellccom)HJ Harkins Co Inc (httphjharkinscompanyinccom)Hospira Inc (httpwwwhospiracom)Innoviant Pharmacy Inc (httpwwwinnoviantpharmacycom)Inspire Pharmaceuticals (httpwwwinspirepharmcom)Kaiser Foundation HospitalLake Erie Medical and Surgical SupplyLiberty Pharmaceuticals
1431753131173804 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 612
Major Pharmaceuticals (httpwwwmajorpharmaceuticalscom)Medisca Inc (httpwwwmediscacom)Murfreesboro Pharmaceutical Nursing Supply (httpwwwunitdosesupplycom)Mylan (httpwwwmylancom)Nucare Pharmaceuticals Inc (httpwwwnucarerxcom)Palmetto Pharmaceuticals Inc (httpwwwpalmettopharmcom)Patheon Inc (httpwwwpatheoncom)PDshyRx Pharmaceuticals Inc (httpwwwpdrxcom)Pfizer Inc (httpwwwpfizercom)Pharmaceutical Utilization Management Program VA IncPharmpak Inc (httpwwwpharmpakinccom)Physicians Total Care Inc (httpwwwphysicianstotalcarecom)Pliva Inc (httpwwwplivacom)Preferred Pharmaceuticals Inc (httpwwwpreferredpharmaceuticalscom)Prepackage SpecialistsPrepak Systems Inc (httpwwwprepaksyscom)Public Health Department Seattle and King County (httpwwwkingcountygovhealthserviceshealthaspx)Rebel Distributors Corp (httpwwwrebelrxcom)Redpharm DrugRemedy Repack (httpwwwremedyrepackcom)Sagent Pharmaceuticals (httpwwwsagentpharmacom)Sandoz (httpwwwsandozca)Sicor PharmaceuticalsSouthwood Pharmaceuticals (httpwwwsouthwoodhealthcarecom)Stat Rx Usa (httpstatrxusaexporteruscom)Stat Scripts LLC (httpwwwstatshyscriptscom)Strides Arcolab Limited (httpwwwstridesarcocom)Teva Pharmaceutical Industries Ltd (httpwwwtevapharmcom)Tya PharmaceuticalsUDL Laboratories (httpwwwudllabscom)US Pharmaceutical GroupWarner Chilcott Co Inc (httpirwcrxcom)Wockhardt Ltd (httpwwwwockhardtincom)
Dosage forms
Form Route Strength
Injection intravenous 500 mg10mL
Injection powder lyophilized for solution intravenous 100 mgmL
Injection powder lyophilized for solution intravenous 2 mgmL
Injection powder lyophilized for solution intravenous 500 mg5mL
Powder for suspension oral 100 mg
Powder for suspension oral 200 mg
Powder for suspension oral 1 g
Powder for suspension oral 100 mg5mL
Powder for suspension oral 1200 mg30mL
Powder for suspension oral 2 g60mL
Prices
Unit description Cost Unit
AposhyAzithromycin 250 mg Tablet 311USD tablet
Azasite 1 eye drops 4285USD ml
Azithromycin 25 gm bulk vial 756USD each
Azithromycin 200 mg5ml Suspension 15ml Bottle 3425USD bottle
Azithromycin 250 mg tablet 633USD tablet
Azithromycin 3 500 mg tablet Disp Pack 4852USD disp
Azithromycin 500 mg tablet 1587USD tablet
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1
1431753131233812 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 712
Azithromycin 6 250 mg tablet Disp Pack 4852USD disp
Azithromycin 600 mg tablet 1904USD tablet
Azithromycin iv 500 mg vial 1109USD each
DrugBank does not sell nor buy drugs Pricing information is supplied for informational purposes only
Patents
Country Patent Number Approved Expires (estimated)
Canada 2148071 2000shy10shy17 2015shy04shy27
Canada 2467611 2010shy03shy30 2024shy05shy18
United States 5192535 1993shy03shy09 2010shy03shy09
United States 6984403 2004shy02shy14 2024shy02shy14
Properties
State Solid
ExperimentalProperties
Property Value Source
melting point 114 degC PhysProp
water solubility slight Not Available
logP 402 MCFARLANDJW ET AL (1997)
pKa 874 (at 25 degC) MCFARLANDJW ET AL (1997)
PredictedProperties
Property Value Source
Water Solubility 0514 mgmL ALOGPS (httpwwwvcclaborglabalogps)
logP 303 ALOGPS (httpwwwvcclaborglabalogps)
logP 244 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorslogp_logd)
logS shy32 ALOGPS (httpwwwvcclaborglabalogps)
pKa (Strongest Acidic) 1243 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
pKa (Strongest Basic) 957 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Physiological Charge 2 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Hydrogen Acceptor Count 13 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Hydrogen Donor Count 5 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Polar Surface Area 18008 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopolgical_surface)
Rotatable Bond Count 7 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Refractivity 19411 m middotmol ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsrefractivity)
Polarizability 8311 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Number of Rings 3 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Bioavailability 0 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Rule of Five Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Ghose Filter Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Vebers Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
MDDRshylike Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Spectra
Mass Spec (NIST) Not Available
Spectra Not Available
References
SynthesisReference
William Heggie Zita Maria De Mouro Vaz Azevedo Mendes ldquoProcess for the preparation of azithromycinrdquo US Patent US6013778 issuedNovember 1994
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1431753131264765 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 812
US6013778 (httpswwwgooglecomtbm=ptsq=6013778amptbm=pts)
General Reference 1 Noedl H Krudsood S Chalermratana K Silachamroon U Leowattana W Tangpukdee N Looareesuwan S Miller RS Fukuda M JongsakulK Sriwichai S Rowan J Bhattacharyya H Ohrt C Knirsch C Azithromycin combination therapy with artesunate or quinine for the treatmentof uncomplicated Plasmodium falciparum malaria in adults a randomized phase 2 clinical trial in Thailand Clin Infect Dis 2006 Nov1543(10)1264shy71 Epub 2006 Oct 12 Pubmed (httpwwwncbinlmnihgovpubmed17051490)
External Links Resource Link
KEGG Compound C06838 (httpwwwgenomejpdbgetshybinwww_bgetcpdC06838)
BindingDB 50197040 (httpwwwbindingdborgbindchemsearchmarvinMolStructurejspmonomerid=50197040)
ChEBI 2955 (httpwwwebiacukchebisearchIddochebiId=2955)
ChEMBL CHEMBL529 (httpwwwebiacukchembldbindexphpcompoundinspectCHEMBL529)
Therapeutic Targets Database DNC001539 (httpbiddnusedusggroupcjttdZFTTDDRUGaspID=DNC001539)
PharmGKB PA448519 (httpwwwpharmgkborgdrugPA448519)
HET ZIT (httpwwwebiacukmsdshysrvchempdbcgishybincgiplFUNCTION=getByCodeampCODE=ZIT)
RxList httpwwwrxlistcomcgigenericzithromaxhtm (httpwwwrxlistcomcgigenericzithromaxhtm)
Drugscom httpwwwdrugscomcdiazithromycinshydropshtml (httpwwwdrugscomcdiazithromycinshydropshtml)
Wikipedia Azithromycin (httpenwikipediaorgwikiAzithromycin)
ATC Codes J01FA10J mdash ANTIINFECTIVES FOR SYSTEMIC USE (atcJJ)J01 mdash ANTIBACTERIALS FOR SYSTEMIC USE (atcJ01J01)J01F mdash MACROLIDES LINCOSAMIDES AND STREPTOGRAMINS (atcJ01FJ01F)J01FA mdash Macrolides (atcJ01FAJ01FA)
S01AA26S mdash SENSORY ORGANS (atcSS)S01 mdash OPHTHALMOLOGICALS (atcS01S01)S01A mdash ANTIINFECTIVES (atcS01AS01A)S01AA mdash Antibiotics (atcS01AAS01AA)
AHFS Codes 08121292
PDB Entries Not Available
FDA label Download (systemfda_labelsDB00207pdf1265922797) (763 KB)
MSDS Download (systemmsdsDB00207pdf1265922737) (739 KB)
Interactions
Drug Interactions Drug
Acenocoumarol(drugsDB01418)
Azithromycin may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration
Anisindione (drugsDB01125) Azithromycin may increase the anticoagulant effect of anisindione by increasing its serum concentration
Artemether (drugsDB06697) Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Cyclosporine(drugsDB00091)
The macrolide azithromycin may increase the effect of cyclosporine
Dicoumarol (drugsDB00266) Azithromycin may increase the anticoagulant effect of dicumarol by increasing its serum concentration
Disopyramide(drugsDB00280)
The macrolide azithromycin may increase the effect of disopyramide
Lovastatin (drugsDB00227) The macrolide antibiotic azithromycin may increase the serum concentration of lovastatin by decreasing its metabolismMonitor for changes in the therapeutic and adverse effects of lovastatin if azithromycin is initiated discontinued or dosechanged
Lumefantrine(drugsDB06708)
Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Vismodegib (drugsDB08828) Pshyglycoprotein inhibitors may increase the chance of adverse drug reactions
Vorinostat (drugsDB02546) Additive QTc prolongation may occur Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsadede Pointes (TdP)
Warfarin (drugsDB00682) Azithromycin may increase the anticoagulant effect of warfarin by increasing its serum concentration
Ziprasidone (drugsDB00246) Additive QTcshyprolonging effects may increase the risk of severe arrhythmias Concomitant therapy is contraindicated
Zuclopenthixol(drugsDB01624)
Additive QTc prolongation may occur Consider alternate therapy or use caution and monitor for QTc prolongation as this canlead to Torsade de Pointes (TdP)
Food Interactions Do not take Aluminum or magnesium antacids or supplements while on this medication
1431753131298898 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 912
Take on empty stomach 1 hour before or 2 hours after meals
Targets
1 23S rRNA (biodbbio_entitiesBE0004800)
Kind nucleotide
Organism Enteric bacteria and other eubacteria
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
References1 Ng LK Martin I Liu G Bryden L Mutation in 23S rRNA associated with macrolide resistance in Neisseria gonorrhoeae Antimicrob Agents Chemother 2002 Sep46(9)3020shy5
Pubmed (httpwwwncbinlmnihgovpubmed12183262)2 Jalava J Vaara M Huovinen P Mutation at the position 2058 of the 23S rRNA as a cause of macrolide resistance in Streptococcus pyogenes Ann Clin Microbiol Antimicrob
2004 May 635 Pubmed (httpwwwncbinlmnihgovpubmed15128458)3 Pereyre S Renaudin H Charron A Bebear C Bebear CM Emergence of a 23S rRNA mutation in Mycoplasma hominis associated with a loss of the intrinsic resistance to
erythromycin and azithromycin J Antimicrob Chemother 2006 Apr57(4)753shy6 Epub 2006 Feb 7 Pubmed (httpwwwncbinlmnihgovpubmed16464889)
2 50S ribosomal protein L4 (biodbbio_entitiesBE0002465)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L4 P60725 (httpwwwuniprotorguniprotP60725) Details (biodbpolypeptidesP60725)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr
22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003
Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan
30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy
24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
3 50S ribosomal protein L22 (biodbbio_entitiesBE0002464)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L22 P61177 (httpwwwuniprotorguniprotP61177) Details (biodbpolypeptidesP61177)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)
1431753131328023 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1012
2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)
3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)
4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)
5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
Enzymes
1 Cytochrome P450 2A6 (biodbbio_entitiesBE0003336)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 2A6 P11509 (httpwwwuniprotorguniprotP11509) Details (biodbpolypeptidesP11509)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
2 Cytochrome P450 3A4 (biodbbio_entitiesBE0002638)
Kind protein
Organism Human
Pharmacological action unknown
Actions substrate inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A4 P08684 (httpwwwuniprotorguniprotP08684) Details (biodbpolypeptidesP08684)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
3 Cytochrome P450 1A2 (biodbbio_entitiesBE0002433)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 1A2 P05177 (httpwwwuniprotorguniprotP05177) Details (biodbpolypeptidesP05177)
References1 Lexicomp
1431753131353312 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1112
(httpwwwcihrshyirscgcca) (httpwwwmetabolomicscentreca)
Transporters
1 Multidrug resistance protein 1 (biodbbio_entitiesBE0001032)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Multidrug resistance protein 1 P08183 (httpwwwuniprotorguniprotP08183) Details (biodbpolypeptidesP08183)
References1 Wang E Lew K Barecki M Casciano CN Clement RP Johnson WW Quantitative distinctions of active site molecular recognition by Pshyglycoprotein and cytochrome P450 3A4
Chem Res Toxicol 2001 Dec14(12)1596shy603 Pubmed (httpwwwncbinlmnihgovpubmed11743742)2 Asakura E Nakayama H Sugie M Zhao YL Nadai M Kitaichi K Shimizu A Miyoshi M Takagi K Takagi K Hasegawa T Azithromycin reverses anticancer drug resistance and
modifies hepatobiliary excretion of doxorubicin in rats Eur J Pharmacol 2004 Jan 26484(2shy3)333shy9 Pubmed (httpwwwncbinlmnihgovpubmed14744620)
Comments
Abiraterone (DB05812)4 comments bull 2 years ago
Adam Maciejewski mdash Hi PangPangGun Thanks for your questionCurrently we dont have this feature but please look at our currentpharmacoeconomics section for information regarding pricesmanufacturers packagers and dosages Thank you Adam
Denosumab (DB06643)1 comment bull 2 years ago
Glenn Pilkington mdash Tsequences you have listed are different to thepatent (WO 2013181575 A2) sequences and the heavy chain sequenceis for a hIgG1 not hIgG2
LYMshy2 (DB05788)2 comments bull a year ago
Adam Maciejewski mdash Hi Nie Lun thank you for letting us know about thisI have created a biotech entry for LYMshy2 and have merged the twodrugs Please see DB09025 Thank you
FTY 720 (DB05286)2 comments bull a year ago
Adam Maciejewski mdash Hello Daniel Himmelstein thank you for pointingthis out Indeed FTY720 is the same drug as the later approvedFingolimod I will merge the two entries into DB08868 If you have anyfurther questions or comments please dont hesitate to hellip
ALSO ON DRUGBANK
2 Comments DrugBank Login1
Share Sort by Best
Join the discussionhellip
bull Reply bull
Bmorale2 bull 3 years ago
I think the Spanish version of this should be translated to Azitromicina not as it shows as Aritromicina
bull Reply bull
Craig Knox bull 3 years agoMod gt Bmorale2
Hi thanks for the tip looks like it was a spelling error Ive corrected it 1
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Drug created on June 13 2005 0724 Updated on September 16 2013 1708
1431753133823464 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1212
(httpwwwaihealthsolutionsca) (httpgenomealbertaca) (httpgenomebcca)
(httpgenomecanadaca)
This project is supported by the Canadian Institutes of Health Research (httpwwwcihrshyirscgcca) (award 111062) Alberta Innovates shy Health Solutions(httpwwwaihealthsolutionsca) and by The Metabolomics Innovation Centre (TMIC) (httpwwwmetabolomicscentreca) a nationallyshyfunded research and corefacility that supports a wide range of cuttingshyedge metabolomic studies TMIC is funded by Genome Alberta (httpwwwgenomealbertaca) Genome British Columbia(httpwwwgenomebcca) and Genome Canada (httpwwwgenomecanadaca) a notshyforshyprofit organization that is leading Canadas national genomics strategy with$900 million in funding from the federal government
DrugBank Version 42 mdash Contact Us (httpdrugbankwcontact)
1431753130949864 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 412
Carboxylic acid ester12shydiol12shyaminoalcoholOxacycleAzacycleOrganoheterocyclic compoundMonocarboxylic acid or derivativesEtherDialkyl etherCarboxylic acid derivativeAcetalHydrocarbon derivativeOrganooxygen compoundOrganonitrogen compoundCarbonyl groupAmineAlcoholAliphatic heteromonocyclic compound
MolecularFramework
Aliphatic heteromonocyclic compounds
ExternalDescriptors
macrolide antibiotic (CHEBI2955 (httpwwwebiacukchebisearchIddochebiId=CHEBI2955))
Pharmacology
Indication For the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the specificconditions H influenzae M catarrhalis S pneumoniae C pneumoniae M pneumoniae S pyogenes S aureus S agal
Pharmacodynamics Azithromycin a semisynthetic antibiotic belonging to the macrolide subgroup of azalides is used to treat STDs due to chlamydia and gonorrheacommunityshyacquired pneumonia pelvic inflammatory disease pediatric otitis media and pharyngitis and Mycobacterium avium complex (MAC) inpatients with advanced HIV disease Similar in structure to erythromycin azithromycin reaches higher intracellular concentrations thanerythromycin increasing its efficacy and duration of action
Mechanism ofaction
Azithromycin binds to the 50S subunit of the 70S bacterial ribosomes and therefore inhibits RNAshydependent protein synthesis in bacterial cells
Absorption Bioavailability is 37 following oral administration Absorption is not affected by food Azithromycin is extensively distributed in tissues with tissueconcentrations reaching up to 50 times greater than plasma concentrations Drug becomes concentrated within macrophages andpolymorphonucleocytes giving it good activity against Chlamydia trachomatis
Volume ofdistribution
311 Lkg
Protein binding Serum protein binding is variable in the concentration range approximating human exposure decreasing from 51 at 002 microgmL to 7 at 2microgmL
Metabolism Hepatic In vitro and in vivo studies to assess the metabolism of azithromycin have not been performed
Route ofelimination
Biliary excretion of azithromycin predominantly as unchanged drug is a major route of elimination
Half life 68 hours
Clearance apparent plasma cl=630 mLmin [following single 500 mg oral and iv doses]
Toxicity Potentially serious side effects of angioedema and cholestatic jaundice were reported
Affected organisms Enteric bacteria and other eubacteria
Pathways Pathway Category SMPDB ID
Azithromycin Action Pathway Drug action SMP00247 (httpsmpdbcaviewSMP00247highlight[compounds][]=DB00207amphighlight[proteins][]=DB00207)
SNP MediatedEffects
Not Available
SNP MediatedAdverse DrugReactions
Not Available
ADMET
Predicted ADMETfeatures
Property Value Probability
Human Intestinal Absorption shy 05518
Blood Brain Barrier shy 09739
Cacoshy2 permeable shy 07578
1431753131115435 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 512
Pshyglycoprotein substrate Substrate 08765
Pshyglycoprotein inhibitor I Inhibitor 08513
Pshyglycoprotein inhibitor II Nonshyinhibitor 08893
Renal organic cation transporter Nonshyinhibitor 08753
CYP450 2C9 substrate Nonshysubstrate 08373
CYP450 2D6 substrate Nonshysubstrate 09116
CYP450 3A4 substrate Substrate 06403
CYP450 1A2 substrate Nonshyinhibitor 09295
CYP450 2C9 substrate Nonshyinhibitor 09021
CYP450 2D6 substrate Nonshyinhibitor 08904
CYP450 2C19 substrate Nonshyinhibitor 09023
CYP450 3A4 substrate Nonshyinhibitor 09533
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 09751
Ames test Non AMES toxic 09133
Carcinogenicity Nonshycarcinogens 09397
Biodegradation Not ready biodegradable 09673
Rat acute toxicity 25423 LD50 molkg Not applicable
hERG inhibition (predictor I) Weak inhibitor 09929
hERG inhibition (predictor II) Nonshyinhibitor 08555
Pharmacoeconomics
Manufacturers Pfizer chemicals div pfizer incPfizer global research developmentPliva incSandoz incTeva pharmaceuticals usaPfizer central researchApp pharmaceuticals llcGland pharma ltdHospira incPliva hrvatska dooSagent strides llcTeva parenteral medicines incPfizer inc (httpwwwpfizercom)Inspire pharmaceuticals incMylan pharmaceuticals incTeva pharmaceuticals usa incWockhardt ltd
Packagers Advanced Pharmaceutical Services IncAidarex Pharmacuticals LLC (httpwwwaidarexcom)Amerisource Health Services Corp (httpwwwamerisourcebergencom)Apotheca IncAPP Pharmaceuticals (httpwwwapppharmacom)AQ Pharmaceuticals Inc (httpwwwaqpharmaceuticalscom)AshyS Medication Solutions LLC (httpordersashysmedscom)Baxter International Inc (httpwwwbaxtercom)Cardinal Health (httpwwwcardinalcom)Catalent Pharma Solutions (httpwwwcatalentcom)Comprehensive Consultant Services IncDept Health Central PharmacyDirect Dispensing IncDispensing Solutions (httpwwwdrxdispensingcom)Diversified Healthcare Services Inc (httpwwwdhscorpcom)Eon LabsGreenstone LLC (httpwwwgreenstonellccom)HJ Harkins Co Inc (httphjharkinscompanyinccom)Hospira Inc (httpwwwhospiracom)Innoviant Pharmacy Inc (httpwwwinnoviantpharmacycom)Inspire Pharmaceuticals (httpwwwinspirepharmcom)Kaiser Foundation HospitalLake Erie Medical and Surgical SupplyLiberty Pharmaceuticals
1431753131173804 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 612
Major Pharmaceuticals (httpwwwmajorpharmaceuticalscom)Medisca Inc (httpwwwmediscacom)Murfreesboro Pharmaceutical Nursing Supply (httpwwwunitdosesupplycom)Mylan (httpwwwmylancom)Nucare Pharmaceuticals Inc (httpwwwnucarerxcom)Palmetto Pharmaceuticals Inc (httpwwwpalmettopharmcom)Patheon Inc (httpwwwpatheoncom)PDshyRx Pharmaceuticals Inc (httpwwwpdrxcom)Pfizer Inc (httpwwwpfizercom)Pharmaceutical Utilization Management Program VA IncPharmpak Inc (httpwwwpharmpakinccom)Physicians Total Care Inc (httpwwwphysicianstotalcarecom)Pliva Inc (httpwwwplivacom)Preferred Pharmaceuticals Inc (httpwwwpreferredpharmaceuticalscom)Prepackage SpecialistsPrepak Systems Inc (httpwwwprepaksyscom)Public Health Department Seattle and King County (httpwwwkingcountygovhealthserviceshealthaspx)Rebel Distributors Corp (httpwwwrebelrxcom)Redpharm DrugRemedy Repack (httpwwwremedyrepackcom)Sagent Pharmaceuticals (httpwwwsagentpharmacom)Sandoz (httpwwwsandozca)Sicor PharmaceuticalsSouthwood Pharmaceuticals (httpwwwsouthwoodhealthcarecom)Stat Rx Usa (httpstatrxusaexporteruscom)Stat Scripts LLC (httpwwwstatshyscriptscom)Strides Arcolab Limited (httpwwwstridesarcocom)Teva Pharmaceutical Industries Ltd (httpwwwtevapharmcom)Tya PharmaceuticalsUDL Laboratories (httpwwwudllabscom)US Pharmaceutical GroupWarner Chilcott Co Inc (httpirwcrxcom)Wockhardt Ltd (httpwwwwockhardtincom)
Dosage forms
Form Route Strength
Injection intravenous 500 mg10mL
Injection powder lyophilized for solution intravenous 100 mgmL
Injection powder lyophilized for solution intravenous 2 mgmL
Injection powder lyophilized for solution intravenous 500 mg5mL
Powder for suspension oral 100 mg
Powder for suspension oral 200 mg
Powder for suspension oral 1 g
Powder for suspension oral 100 mg5mL
Powder for suspension oral 1200 mg30mL
Powder for suspension oral 2 g60mL
Prices
Unit description Cost Unit
AposhyAzithromycin 250 mg Tablet 311USD tablet
Azasite 1 eye drops 4285USD ml
Azithromycin 25 gm bulk vial 756USD each
Azithromycin 200 mg5ml Suspension 15ml Bottle 3425USD bottle
Azithromycin 250 mg tablet 633USD tablet
Azithromycin 3 500 mg tablet Disp Pack 4852USD disp
Azithromycin 500 mg tablet 1587USD tablet
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1
1431753131233812 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 712
Azithromycin 6 250 mg tablet Disp Pack 4852USD disp
Azithromycin 600 mg tablet 1904USD tablet
Azithromycin iv 500 mg vial 1109USD each
DrugBank does not sell nor buy drugs Pricing information is supplied for informational purposes only
Patents
Country Patent Number Approved Expires (estimated)
Canada 2148071 2000shy10shy17 2015shy04shy27
Canada 2467611 2010shy03shy30 2024shy05shy18
United States 5192535 1993shy03shy09 2010shy03shy09
United States 6984403 2004shy02shy14 2024shy02shy14
Properties
State Solid
ExperimentalProperties
Property Value Source
melting point 114 degC PhysProp
water solubility slight Not Available
logP 402 MCFARLANDJW ET AL (1997)
pKa 874 (at 25 degC) MCFARLANDJW ET AL (1997)
PredictedProperties
Property Value Source
Water Solubility 0514 mgmL ALOGPS (httpwwwvcclaborglabalogps)
logP 303 ALOGPS (httpwwwvcclaborglabalogps)
logP 244 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorslogp_logd)
logS shy32 ALOGPS (httpwwwvcclaborglabalogps)
pKa (Strongest Acidic) 1243 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
pKa (Strongest Basic) 957 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Physiological Charge 2 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Hydrogen Acceptor Count 13 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Hydrogen Donor Count 5 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Polar Surface Area 18008 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopolgical_surface)
Rotatable Bond Count 7 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Refractivity 19411 m middotmol ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsrefractivity)
Polarizability 8311 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Number of Rings 3 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Bioavailability 0 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Rule of Five Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Ghose Filter Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Vebers Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
MDDRshylike Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Spectra
Mass Spec (NIST) Not Available
Spectra Not Available
References
SynthesisReference
William Heggie Zita Maria De Mouro Vaz Azevedo Mendes ldquoProcess for the preparation of azithromycinrdquo US Patent US6013778 issuedNovember 1994
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1
1431753131264765 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 812
US6013778 (httpswwwgooglecomtbm=ptsq=6013778amptbm=pts)
General Reference 1 Noedl H Krudsood S Chalermratana K Silachamroon U Leowattana W Tangpukdee N Looareesuwan S Miller RS Fukuda M JongsakulK Sriwichai S Rowan J Bhattacharyya H Ohrt C Knirsch C Azithromycin combination therapy with artesunate or quinine for the treatmentof uncomplicated Plasmodium falciparum malaria in adults a randomized phase 2 clinical trial in Thailand Clin Infect Dis 2006 Nov1543(10)1264shy71 Epub 2006 Oct 12 Pubmed (httpwwwncbinlmnihgovpubmed17051490)
External Links Resource Link
KEGG Compound C06838 (httpwwwgenomejpdbgetshybinwww_bgetcpdC06838)
BindingDB 50197040 (httpwwwbindingdborgbindchemsearchmarvinMolStructurejspmonomerid=50197040)
ChEBI 2955 (httpwwwebiacukchebisearchIddochebiId=2955)
ChEMBL CHEMBL529 (httpwwwebiacukchembldbindexphpcompoundinspectCHEMBL529)
Therapeutic Targets Database DNC001539 (httpbiddnusedusggroupcjttdZFTTDDRUGaspID=DNC001539)
PharmGKB PA448519 (httpwwwpharmgkborgdrugPA448519)
HET ZIT (httpwwwebiacukmsdshysrvchempdbcgishybincgiplFUNCTION=getByCodeampCODE=ZIT)
RxList httpwwwrxlistcomcgigenericzithromaxhtm (httpwwwrxlistcomcgigenericzithromaxhtm)
Drugscom httpwwwdrugscomcdiazithromycinshydropshtml (httpwwwdrugscomcdiazithromycinshydropshtml)
Wikipedia Azithromycin (httpenwikipediaorgwikiAzithromycin)
ATC Codes J01FA10J mdash ANTIINFECTIVES FOR SYSTEMIC USE (atcJJ)J01 mdash ANTIBACTERIALS FOR SYSTEMIC USE (atcJ01J01)J01F mdash MACROLIDES LINCOSAMIDES AND STREPTOGRAMINS (atcJ01FJ01F)J01FA mdash Macrolides (atcJ01FAJ01FA)
S01AA26S mdash SENSORY ORGANS (atcSS)S01 mdash OPHTHALMOLOGICALS (atcS01S01)S01A mdash ANTIINFECTIVES (atcS01AS01A)S01AA mdash Antibiotics (atcS01AAS01AA)
AHFS Codes 08121292
PDB Entries Not Available
FDA label Download (systemfda_labelsDB00207pdf1265922797) (763 KB)
MSDS Download (systemmsdsDB00207pdf1265922737) (739 KB)
Interactions
Drug Interactions Drug
Acenocoumarol(drugsDB01418)
Azithromycin may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration
Anisindione (drugsDB01125) Azithromycin may increase the anticoagulant effect of anisindione by increasing its serum concentration
Artemether (drugsDB06697) Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Cyclosporine(drugsDB00091)
The macrolide azithromycin may increase the effect of cyclosporine
Dicoumarol (drugsDB00266) Azithromycin may increase the anticoagulant effect of dicumarol by increasing its serum concentration
Disopyramide(drugsDB00280)
The macrolide azithromycin may increase the effect of disopyramide
Lovastatin (drugsDB00227) The macrolide antibiotic azithromycin may increase the serum concentration of lovastatin by decreasing its metabolismMonitor for changes in the therapeutic and adverse effects of lovastatin if azithromycin is initiated discontinued or dosechanged
Lumefantrine(drugsDB06708)
Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Vismodegib (drugsDB08828) Pshyglycoprotein inhibitors may increase the chance of adverse drug reactions
Vorinostat (drugsDB02546) Additive QTc prolongation may occur Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsadede Pointes (TdP)
Warfarin (drugsDB00682) Azithromycin may increase the anticoagulant effect of warfarin by increasing its serum concentration
Ziprasidone (drugsDB00246) Additive QTcshyprolonging effects may increase the risk of severe arrhythmias Concomitant therapy is contraindicated
Zuclopenthixol(drugsDB01624)
Additive QTc prolongation may occur Consider alternate therapy or use caution and monitor for QTc prolongation as this canlead to Torsade de Pointes (TdP)
Food Interactions Do not take Aluminum or magnesium antacids or supplements while on this medication
1431753131298898 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 912
Take on empty stomach 1 hour before or 2 hours after meals
Targets
1 23S rRNA (biodbbio_entitiesBE0004800)
Kind nucleotide
Organism Enteric bacteria and other eubacteria
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
References1 Ng LK Martin I Liu G Bryden L Mutation in 23S rRNA associated with macrolide resistance in Neisseria gonorrhoeae Antimicrob Agents Chemother 2002 Sep46(9)3020shy5
Pubmed (httpwwwncbinlmnihgovpubmed12183262)2 Jalava J Vaara M Huovinen P Mutation at the position 2058 of the 23S rRNA as a cause of macrolide resistance in Streptococcus pyogenes Ann Clin Microbiol Antimicrob
2004 May 635 Pubmed (httpwwwncbinlmnihgovpubmed15128458)3 Pereyre S Renaudin H Charron A Bebear C Bebear CM Emergence of a 23S rRNA mutation in Mycoplasma hominis associated with a loss of the intrinsic resistance to
erythromycin and azithromycin J Antimicrob Chemother 2006 Apr57(4)753shy6 Epub 2006 Feb 7 Pubmed (httpwwwncbinlmnihgovpubmed16464889)
2 50S ribosomal protein L4 (biodbbio_entitiesBE0002465)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L4 P60725 (httpwwwuniprotorguniprotP60725) Details (biodbpolypeptidesP60725)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr
22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003
Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan
30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy
24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
3 50S ribosomal protein L22 (biodbbio_entitiesBE0002464)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L22 P61177 (httpwwwuniprotorguniprotP61177) Details (biodbpolypeptidesP61177)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)
1431753131328023 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1012
2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)
3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)
4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)
5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
Enzymes
1 Cytochrome P450 2A6 (biodbbio_entitiesBE0003336)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 2A6 P11509 (httpwwwuniprotorguniprotP11509) Details (biodbpolypeptidesP11509)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
2 Cytochrome P450 3A4 (biodbbio_entitiesBE0002638)
Kind protein
Organism Human
Pharmacological action unknown
Actions substrate inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A4 P08684 (httpwwwuniprotorguniprotP08684) Details (biodbpolypeptidesP08684)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
3 Cytochrome P450 1A2 (biodbbio_entitiesBE0002433)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 1A2 P05177 (httpwwwuniprotorguniprotP05177) Details (biodbpolypeptidesP05177)
References1 Lexicomp
1431753131353312 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1112
(httpwwwcihrshyirscgcca) (httpwwwmetabolomicscentreca)
Transporters
1 Multidrug resistance protein 1 (biodbbio_entitiesBE0001032)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Multidrug resistance protein 1 P08183 (httpwwwuniprotorguniprotP08183) Details (biodbpolypeptidesP08183)
References1 Wang E Lew K Barecki M Casciano CN Clement RP Johnson WW Quantitative distinctions of active site molecular recognition by Pshyglycoprotein and cytochrome P450 3A4
Chem Res Toxicol 2001 Dec14(12)1596shy603 Pubmed (httpwwwncbinlmnihgovpubmed11743742)2 Asakura E Nakayama H Sugie M Zhao YL Nadai M Kitaichi K Shimizu A Miyoshi M Takagi K Takagi K Hasegawa T Azithromycin reverses anticancer drug resistance and
modifies hepatobiliary excretion of doxorubicin in rats Eur J Pharmacol 2004 Jan 26484(2shy3)333shy9 Pubmed (httpwwwncbinlmnihgovpubmed14744620)
Comments
Abiraterone (DB05812)4 comments bull 2 years ago
Adam Maciejewski mdash Hi PangPangGun Thanks for your questionCurrently we dont have this feature but please look at our currentpharmacoeconomics section for information regarding pricesmanufacturers packagers and dosages Thank you Adam
Denosumab (DB06643)1 comment bull 2 years ago
Glenn Pilkington mdash Tsequences you have listed are different to thepatent (WO 2013181575 A2) sequences and the heavy chain sequenceis for a hIgG1 not hIgG2
LYMshy2 (DB05788)2 comments bull a year ago
Adam Maciejewski mdash Hi Nie Lun thank you for letting us know about thisI have created a biotech entry for LYMshy2 and have merged the twodrugs Please see DB09025 Thank you
FTY 720 (DB05286)2 comments bull a year ago
Adam Maciejewski mdash Hello Daniel Himmelstein thank you for pointingthis out Indeed FTY720 is the same drug as the later approvedFingolimod I will merge the two entries into DB08868 If you have anyfurther questions or comments please dont hesitate to hellip
ALSO ON DRUGBANK
2 Comments DrugBank Login1
Share Sort by Best
Join the discussionhellip
bull Reply bull
Bmorale2 bull 3 years ago
I think the Spanish version of this should be translated to Azitromicina not as it shows as Aritromicina
bull Reply bull
Craig Knox bull 3 years agoMod gt Bmorale2
Hi thanks for the tip looks like it was a spelling error Ive corrected it 1
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Drug created on June 13 2005 0724 Updated on September 16 2013 1708
1431753133823464 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1212
(httpwwwaihealthsolutionsca) (httpgenomealbertaca) (httpgenomebcca)
(httpgenomecanadaca)
This project is supported by the Canadian Institutes of Health Research (httpwwwcihrshyirscgcca) (award 111062) Alberta Innovates shy Health Solutions(httpwwwaihealthsolutionsca) and by The Metabolomics Innovation Centre (TMIC) (httpwwwmetabolomicscentreca) a nationallyshyfunded research and corefacility that supports a wide range of cuttingshyedge metabolomic studies TMIC is funded by Genome Alberta (httpwwwgenomealbertaca) Genome British Columbia(httpwwwgenomebcca) and Genome Canada (httpwwwgenomecanadaca) a notshyforshyprofit organization that is leading Canadas national genomics strategy with$900 million in funding from the federal government
DrugBank Version 42 mdash Contact Us (httpdrugbankwcontact)
1431753131115435 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 512
Pshyglycoprotein substrate Substrate 08765
Pshyglycoprotein inhibitor I Inhibitor 08513
Pshyglycoprotein inhibitor II Nonshyinhibitor 08893
Renal organic cation transporter Nonshyinhibitor 08753
CYP450 2C9 substrate Nonshysubstrate 08373
CYP450 2D6 substrate Nonshysubstrate 09116
CYP450 3A4 substrate Substrate 06403
CYP450 1A2 substrate Nonshyinhibitor 09295
CYP450 2C9 substrate Nonshyinhibitor 09021
CYP450 2D6 substrate Nonshyinhibitor 08904
CYP450 2C19 substrate Nonshyinhibitor 09023
CYP450 3A4 substrate Nonshyinhibitor 09533
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 09751
Ames test Non AMES toxic 09133
Carcinogenicity Nonshycarcinogens 09397
Biodegradation Not ready biodegradable 09673
Rat acute toxicity 25423 LD50 molkg Not applicable
hERG inhibition (predictor I) Weak inhibitor 09929
hERG inhibition (predictor II) Nonshyinhibitor 08555
Pharmacoeconomics
Manufacturers Pfizer chemicals div pfizer incPfizer global research developmentPliva incSandoz incTeva pharmaceuticals usaPfizer central researchApp pharmaceuticals llcGland pharma ltdHospira incPliva hrvatska dooSagent strides llcTeva parenteral medicines incPfizer inc (httpwwwpfizercom)Inspire pharmaceuticals incMylan pharmaceuticals incTeva pharmaceuticals usa incWockhardt ltd
Packagers Advanced Pharmaceutical Services IncAidarex Pharmacuticals LLC (httpwwwaidarexcom)Amerisource Health Services Corp (httpwwwamerisourcebergencom)Apotheca IncAPP Pharmaceuticals (httpwwwapppharmacom)AQ Pharmaceuticals Inc (httpwwwaqpharmaceuticalscom)AshyS Medication Solutions LLC (httpordersashysmedscom)Baxter International Inc (httpwwwbaxtercom)Cardinal Health (httpwwwcardinalcom)Catalent Pharma Solutions (httpwwwcatalentcom)Comprehensive Consultant Services IncDept Health Central PharmacyDirect Dispensing IncDispensing Solutions (httpwwwdrxdispensingcom)Diversified Healthcare Services Inc (httpwwwdhscorpcom)Eon LabsGreenstone LLC (httpwwwgreenstonellccom)HJ Harkins Co Inc (httphjharkinscompanyinccom)Hospira Inc (httpwwwhospiracom)Innoviant Pharmacy Inc (httpwwwinnoviantpharmacycom)Inspire Pharmaceuticals (httpwwwinspirepharmcom)Kaiser Foundation HospitalLake Erie Medical and Surgical SupplyLiberty Pharmaceuticals
1431753131173804 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 612
Major Pharmaceuticals (httpwwwmajorpharmaceuticalscom)Medisca Inc (httpwwwmediscacom)Murfreesboro Pharmaceutical Nursing Supply (httpwwwunitdosesupplycom)Mylan (httpwwwmylancom)Nucare Pharmaceuticals Inc (httpwwwnucarerxcom)Palmetto Pharmaceuticals Inc (httpwwwpalmettopharmcom)Patheon Inc (httpwwwpatheoncom)PDshyRx Pharmaceuticals Inc (httpwwwpdrxcom)Pfizer Inc (httpwwwpfizercom)Pharmaceutical Utilization Management Program VA IncPharmpak Inc (httpwwwpharmpakinccom)Physicians Total Care Inc (httpwwwphysicianstotalcarecom)Pliva Inc (httpwwwplivacom)Preferred Pharmaceuticals Inc (httpwwwpreferredpharmaceuticalscom)Prepackage SpecialistsPrepak Systems Inc (httpwwwprepaksyscom)Public Health Department Seattle and King County (httpwwwkingcountygovhealthserviceshealthaspx)Rebel Distributors Corp (httpwwwrebelrxcom)Redpharm DrugRemedy Repack (httpwwwremedyrepackcom)Sagent Pharmaceuticals (httpwwwsagentpharmacom)Sandoz (httpwwwsandozca)Sicor PharmaceuticalsSouthwood Pharmaceuticals (httpwwwsouthwoodhealthcarecom)Stat Rx Usa (httpstatrxusaexporteruscom)Stat Scripts LLC (httpwwwstatshyscriptscom)Strides Arcolab Limited (httpwwwstridesarcocom)Teva Pharmaceutical Industries Ltd (httpwwwtevapharmcom)Tya PharmaceuticalsUDL Laboratories (httpwwwudllabscom)US Pharmaceutical GroupWarner Chilcott Co Inc (httpirwcrxcom)Wockhardt Ltd (httpwwwwockhardtincom)
Dosage forms
Form Route Strength
Injection intravenous 500 mg10mL
Injection powder lyophilized for solution intravenous 100 mgmL
Injection powder lyophilized for solution intravenous 2 mgmL
Injection powder lyophilized for solution intravenous 500 mg5mL
Powder for suspension oral 100 mg
Powder for suspension oral 200 mg
Powder for suspension oral 1 g
Powder for suspension oral 100 mg5mL
Powder for suspension oral 1200 mg30mL
Powder for suspension oral 2 g60mL
Prices
Unit description Cost Unit
AposhyAzithromycin 250 mg Tablet 311USD tablet
Azasite 1 eye drops 4285USD ml
Azithromycin 25 gm bulk vial 756USD each
Azithromycin 200 mg5ml Suspension 15ml Bottle 3425USD bottle
Azithromycin 250 mg tablet 633USD tablet
Azithromycin 3 500 mg tablet Disp Pack 4852USD disp
Azithromycin 500 mg tablet 1587USD tablet
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1
1431753131233812 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 712
Azithromycin 6 250 mg tablet Disp Pack 4852USD disp
Azithromycin 600 mg tablet 1904USD tablet
Azithromycin iv 500 mg vial 1109USD each
DrugBank does not sell nor buy drugs Pricing information is supplied for informational purposes only
Patents
Country Patent Number Approved Expires (estimated)
Canada 2148071 2000shy10shy17 2015shy04shy27
Canada 2467611 2010shy03shy30 2024shy05shy18
United States 5192535 1993shy03shy09 2010shy03shy09
United States 6984403 2004shy02shy14 2024shy02shy14
Properties
State Solid
ExperimentalProperties
Property Value Source
melting point 114 degC PhysProp
water solubility slight Not Available
logP 402 MCFARLANDJW ET AL (1997)
pKa 874 (at 25 degC) MCFARLANDJW ET AL (1997)
PredictedProperties
Property Value Source
Water Solubility 0514 mgmL ALOGPS (httpwwwvcclaborglabalogps)
logP 303 ALOGPS (httpwwwvcclaborglabalogps)
logP 244 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorslogp_logd)
logS shy32 ALOGPS (httpwwwvcclaborglabalogps)
pKa (Strongest Acidic) 1243 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
pKa (Strongest Basic) 957 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Physiological Charge 2 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Hydrogen Acceptor Count 13 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Hydrogen Donor Count 5 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Polar Surface Area 18008 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopolgical_surface)
Rotatable Bond Count 7 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Refractivity 19411 m middotmol ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsrefractivity)
Polarizability 8311 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Number of Rings 3 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Bioavailability 0 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Rule of Five Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Ghose Filter Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Vebers Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
MDDRshylike Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Spectra
Mass Spec (NIST) Not Available
Spectra Not Available
References
SynthesisReference
William Heggie Zita Maria De Mouro Vaz Azevedo Mendes ldquoProcess for the preparation of azithromycinrdquo US Patent US6013778 issuedNovember 1994
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1431753131264765 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 812
US6013778 (httpswwwgooglecomtbm=ptsq=6013778amptbm=pts)
General Reference 1 Noedl H Krudsood S Chalermratana K Silachamroon U Leowattana W Tangpukdee N Looareesuwan S Miller RS Fukuda M JongsakulK Sriwichai S Rowan J Bhattacharyya H Ohrt C Knirsch C Azithromycin combination therapy with artesunate or quinine for the treatmentof uncomplicated Plasmodium falciparum malaria in adults a randomized phase 2 clinical trial in Thailand Clin Infect Dis 2006 Nov1543(10)1264shy71 Epub 2006 Oct 12 Pubmed (httpwwwncbinlmnihgovpubmed17051490)
External Links Resource Link
KEGG Compound C06838 (httpwwwgenomejpdbgetshybinwww_bgetcpdC06838)
BindingDB 50197040 (httpwwwbindingdborgbindchemsearchmarvinMolStructurejspmonomerid=50197040)
ChEBI 2955 (httpwwwebiacukchebisearchIddochebiId=2955)
ChEMBL CHEMBL529 (httpwwwebiacukchembldbindexphpcompoundinspectCHEMBL529)
Therapeutic Targets Database DNC001539 (httpbiddnusedusggroupcjttdZFTTDDRUGaspID=DNC001539)
PharmGKB PA448519 (httpwwwpharmgkborgdrugPA448519)
HET ZIT (httpwwwebiacukmsdshysrvchempdbcgishybincgiplFUNCTION=getByCodeampCODE=ZIT)
RxList httpwwwrxlistcomcgigenericzithromaxhtm (httpwwwrxlistcomcgigenericzithromaxhtm)
Drugscom httpwwwdrugscomcdiazithromycinshydropshtml (httpwwwdrugscomcdiazithromycinshydropshtml)
Wikipedia Azithromycin (httpenwikipediaorgwikiAzithromycin)
ATC Codes J01FA10J mdash ANTIINFECTIVES FOR SYSTEMIC USE (atcJJ)J01 mdash ANTIBACTERIALS FOR SYSTEMIC USE (atcJ01J01)J01F mdash MACROLIDES LINCOSAMIDES AND STREPTOGRAMINS (atcJ01FJ01F)J01FA mdash Macrolides (atcJ01FAJ01FA)
S01AA26S mdash SENSORY ORGANS (atcSS)S01 mdash OPHTHALMOLOGICALS (atcS01S01)S01A mdash ANTIINFECTIVES (atcS01AS01A)S01AA mdash Antibiotics (atcS01AAS01AA)
AHFS Codes 08121292
PDB Entries Not Available
FDA label Download (systemfda_labelsDB00207pdf1265922797) (763 KB)
MSDS Download (systemmsdsDB00207pdf1265922737) (739 KB)
Interactions
Drug Interactions Drug
Acenocoumarol(drugsDB01418)
Azithromycin may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration
Anisindione (drugsDB01125) Azithromycin may increase the anticoagulant effect of anisindione by increasing its serum concentration
Artemether (drugsDB06697) Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Cyclosporine(drugsDB00091)
The macrolide azithromycin may increase the effect of cyclosporine
Dicoumarol (drugsDB00266) Azithromycin may increase the anticoagulant effect of dicumarol by increasing its serum concentration
Disopyramide(drugsDB00280)
The macrolide azithromycin may increase the effect of disopyramide
Lovastatin (drugsDB00227) The macrolide antibiotic azithromycin may increase the serum concentration of lovastatin by decreasing its metabolismMonitor for changes in the therapeutic and adverse effects of lovastatin if azithromycin is initiated discontinued or dosechanged
Lumefantrine(drugsDB06708)
Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Vismodegib (drugsDB08828) Pshyglycoprotein inhibitors may increase the chance of adverse drug reactions
Vorinostat (drugsDB02546) Additive QTc prolongation may occur Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsadede Pointes (TdP)
Warfarin (drugsDB00682) Azithromycin may increase the anticoagulant effect of warfarin by increasing its serum concentration
Ziprasidone (drugsDB00246) Additive QTcshyprolonging effects may increase the risk of severe arrhythmias Concomitant therapy is contraindicated
Zuclopenthixol(drugsDB01624)
Additive QTc prolongation may occur Consider alternate therapy or use caution and monitor for QTc prolongation as this canlead to Torsade de Pointes (TdP)
Food Interactions Do not take Aluminum or magnesium antacids or supplements while on this medication
1431753131298898 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 912
Take on empty stomach 1 hour before or 2 hours after meals
Targets
1 23S rRNA (biodbbio_entitiesBE0004800)
Kind nucleotide
Organism Enteric bacteria and other eubacteria
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
References1 Ng LK Martin I Liu G Bryden L Mutation in 23S rRNA associated with macrolide resistance in Neisseria gonorrhoeae Antimicrob Agents Chemother 2002 Sep46(9)3020shy5
Pubmed (httpwwwncbinlmnihgovpubmed12183262)2 Jalava J Vaara M Huovinen P Mutation at the position 2058 of the 23S rRNA as a cause of macrolide resistance in Streptococcus pyogenes Ann Clin Microbiol Antimicrob
2004 May 635 Pubmed (httpwwwncbinlmnihgovpubmed15128458)3 Pereyre S Renaudin H Charron A Bebear C Bebear CM Emergence of a 23S rRNA mutation in Mycoplasma hominis associated with a loss of the intrinsic resistance to
erythromycin and azithromycin J Antimicrob Chemother 2006 Apr57(4)753shy6 Epub 2006 Feb 7 Pubmed (httpwwwncbinlmnihgovpubmed16464889)
2 50S ribosomal protein L4 (biodbbio_entitiesBE0002465)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L4 P60725 (httpwwwuniprotorguniprotP60725) Details (biodbpolypeptidesP60725)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr
22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003
Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan
30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy
24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
3 50S ribosomal protein L22 (biodbbio_entitiesBE0002464)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L22 P61177 (httpwwwuniprotorguniprotP61177) Details (biodbpolypeptidesP61177)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)
1431753131328023 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1012
2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)
3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)
4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)
5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
Enzymes
1 Cytochrome P450 2A6 (biodbbio_entitiesBE0003336)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 2A6 P11509 (httpwwwuniprotorguniprotP11509) Details (biodbpolypeptidesP11509)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
2 Cytochrome P450 3A4 (biodbbio_entitiesBE0002638)
Kind protein
Organism Human
Pharmacological action unknown
Actions substrate inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A4 P08684 (httpwwwuniprotorguniprotP08684) Details (biodbpolypeptidesP08684)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
3 Cytochrome P450 1A2 (biodbbio_entitiesBE0002433)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 1A2 P05177 (httpwwwuniprotorguniprotP05177) Details (biodbpolypeptidesP05177)
References1 Lexicomp
1431753131353312 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1112
(httpwwwcihrshyirscgcca) (httpwwwmetabolomicscentreca)
Transporters
1 Multidrug resistance protein 1 (biodbbio_entitiesBE0001032)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Multidrug resistance protein 1 P08183 (httpwwwuniprotorguniprotP08183) Details (biodbpolypeptidesP08183)
References1 Wang E Lew K Barecki M Casciano CN Clement RP Johnson WW Quantitative distinctions of active site molecular recognition by Pshyglycoprotein and cytochrome P450 3A4
Chem Res Toxicol 2001 Dec14(12)1596shy603 Pubmed (httpwwwncbinlmnihgovpubmed11743742)2 Asakura E Nakayama H Sugie M Zhao YL Nadai M Kitaichi K Shimizu A Miyoshi M Takagi K Takagi K Hasegawa T Azithromycin reverses anticancer drug resistance and
modifies hepatobiliary excretion of doxorubicin in rats Eur J Pharmacol 2004 Jan 26484(2shy3)333shy9 Pubmed (httpwwwncbinlmnihgovpubmed14744620)
Comments
Abiraterone (DB05812)4 comments bull 2 years ago
Adam Maciejewski mdash Hi PangPangGun Thanks for your questionCurrently we dont have this feature but please look at our currentpharmacoeconomics section for information regarding pricesmanufacturers packagers and dosages Thank you Adam
Denosumab (DB06643)1 comment bull 2 years ago
Glenn Pilkington mdash Tsequences you have listed are different to thepatent (WO 2013181575 A2) sequences and the heavy chain sequenceis for a hIgG1 not hIgG2
LYMshy2 (DB05788)2 comments bull a year ago
Adam Maciejewski mdash Hi Nie Lun thank you for letting us know about thisI have created a biotech entry for LYMshy2 and have merged the twodrugs Please see DB09025 Thank you
FTY 720 (DB05286)2 comments bull a year ago
Adam Maciejewski mdash Hello Daniel Himmelstein thank you for pointingthis out Indeed FTY720 is the same drug as the later approvedFingolimod I will merge the two entries into DB08868 If you have anyfurther questions or comments please dont hesitate to hellip
ALSO ON DRUGBANK
2 Comments DrugBank Login1
Share Sort by Best
Join the discussionhellip
bull Reply bull
Bmorale2 bull 3 years ago
I think the Spanish version of this should be translated to Azitromicina not as it shows as Aritromicina
bull Reply bull
Craig Knox bull 3 years agoMod gt Bmorale2
Hi thanks for the tip looks like it was a spelling error Ive corrected it 1
WHATS THIS
Subscribe Add Disqus to your sited Privacy
Recommend 7
Share rsaquo
Share rsaquo
Drug created on June 13 2005 0724 Updated on September 16 2013 1708
1431753133823464 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1212
(httpwwwaihealthsolutionsca) (httpgenomealbertaca) (httpgenomebcca)
(httpgenomecanadaca)
This project is supported by the Canadian Institutes of Health Research (httpwwwcihrshyirscgcca) (award 111062) Alberta Innovates shy Health Solutions(httpwwwaihealthsolutionsca) and by The Metabolomics Innovation Centre (TMIC) (httpwwwmetabolomicscentreca) a nationallyshyfunded research and corefacility that supports a wide range of cuttingshyedge metabolomic studies TMIC is funded by Genome Alberta (httpwwwgenomealbertaca) Genome British Columbia(httpwwwgenomebcca) and Genome Canada (httpwwwgenomecanadaca) a notshyforshyprofit organization that is leading Canadas national genomics strategy with$900 million in funding from the federal government
DrugBank Version 42 mdash Contact Us (httpdrugbankwcontact)
1431753131173804 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 612
Major Pharmaceuticals (httpwwwmajorpharmaceuticalscom)Medisca Inc (httpwwwmediscacom)Murfreesboro Pharmaceutical Nursing Supply (httpwwwunitdosesupplycom)Mylan (httpwwwmylancom)Nucare Pharmaceuticals Inc (httpwwwnucarerxcom)Palmetto Pharmaceuticals Inc (httpwwwpalmettopharmcom)Patheon Inc (httpwwwpatheoncom)PDshyRx Pharmaceuticals Inc (httpwwwpdrxcom)Pfizer Inc (httpwwwpfizercom)Pharmaceutical Utilization Management Program VA IncPharmpak Inc (httpwwwpharmpakinccom)Physicians Total Care Inc (httpwwwphysicianstotalcarecom)Pliva Inc (httpwwwplivacom)Preferred Pharmaceuticals Inc (httpwwwpreferredpharmaceuticalscom)Prepackage SpecialistsPrepak Systems Inc (httpwwwprepaksyscom)Public Health Department Seattle and King County (httpwwwkingcountygovhealthserviceshealthaspx)Rebel Distributors Corp (httpwwwrebelrxcom)Redpharm DrugRemedy Repack (httpwwwremedyrepackcom)Sagent Pharmaceuticals (httpwwwsagentpharmacom)Sandoz (httpwwwsandozca)Sicor PharmaceuticalsSouthwood Pharmaceuticals (httpwwwsouthwoodhealthcarecom)Stat Rx Usa (httpstatrxusaexporteruscom)Stat Scripts LLC (httpwwwstatshyscriptscom)Strides Arcolab Limited (httpwwwstridesarcocom)Teva Pharmaceutical Industries Ltd (httpwwwtevapharmcom)Tya PharmaceuticalsUDL Laboratories (httpwwwudllabscom)US Pharmaceutical GroupWarner Chilcott Co Inc (httpirwcrxcom)Wockhardt Ltd (httpwwwwockhardtincom)
Dosage forms
Form Route Strength
Injection intravenous 500 mg10mL
Injection powder lyophilized for solution intravenous 100 mgmL
Injection powder lyophilized for solution intravenous 2 mgmL
Injection powder lyophilized for solution intravenous 500 mg5mL
Powder for suspension oral 100 mg
Powder for suspension oral 200 mg
Powder for suspension oral 1 g
Powder for suspension oral 100 mg5mL
Powder for suspension oral 1200 mg30mL
Powder for suspension oral 2 g60mL
Prices
Unit description Cost Unit
AposhyAzithromycin 250 mg Tablet 311USD tablet
Azasite 1 eye drops 4285USD ml
Azithromycin 25 gm bulk vial 756USD each
Azithromycin 200 mg5ml Suspension 15ml Bottle 3425USD bottle
Azithromycin 250 mg tablet 633USD tablet
Azithromycin 3 500 mg tablet Disp Pack 4852USD disp
Azithromycin 500 mg tablet 1587USD tablet
Show10
entries
Search
Showing 1 to 10 of 20 entries Previous 2 Next
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entries
Search
1
1431753131233812 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 712
Azithromycin 6 250 mg tablet Disp Pack 4852USD disp
Azithromycin 600 mg tablet 1904USD tablet
Azithromycin iv 500 mg vial 1109USD each
DrugBank does not sell nor buy drugs Pricing information is supplied for informational purposes only
Patents
Country Patent Number Approved Expires (estimated)
Canada 2148071 2000shy10shy17 2015shy04shy27
Canada 2467611 2010shy03shy30 2024shy05shy18
United States 5192535 1993shy03shy09 2010shy03shy09
United States 6984403 2004shy02shy14 2024shy02shy14
Properties
State Solid
ExperimentalProperties
Property Value Source
melting point 114 degC PhysProp
water solubility slight Not Available
logP 402 MCFARLANDJW ET AL (1997)
pKa 874 (at 25 degC) MCFARLANDJW ET AL (1997)
PredictedProperties
Property Value Source
Water Solubility 0514 mgmL ALOGPS (httpwwwvcclaborglabalogps)
logP 303 ALOGPS (httpwwwvcclaborglabalogps)
logP 244 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorslogp_logd)
logS shy32 ALOGPS (httpwwwvcclaborglabalogps)
pKa (Strongest Acidic) 1243 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
pKa (Strongest Basic) 957 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Physiological Charge 2 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Hydrogen Acceptor Count 13 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Hydrogen Donor Count 5 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Polar Surface Area 18008 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopolgical_surface)
Rotatable Bond Count 7 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Refractivity 19411 m middotmol ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsrefractivity)
Polarizability 8311 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Number of Rings 3 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Bioavailability 0 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Rule of Five Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Ghose Filter Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Vebers Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
MDDRshylike Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Spectra
Mass Spec (NIST) Not Available
Spectra Not Available
References
SynthesisReference
William Heggie Zita Maria De Mouro Vaz Azevedo Mendes ldquoProcess for the preparation of azithromycinrdquo US Patent US6013778 issuedNovember 1994
Showing 1 to 10 of 45 entries Previous 2 3 4 5 Next
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Showing 1 to 4 of 4 entries Previous Next
2
3 shy1
3
1
1
1431753131264765 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 812
US6013778 (httpswwwgooglecomtbm=ptsq=6013778amptbm=pts)
General Reference 1 Noedl H Krudsood S Chalermratana K Silachamroon U Leowattana W Tangpukdee N Looareesuwan S Miller RS Fukuda M JongsakulK Sriwichai S Rowan J Bhattacharyya H Ohrt C Knirsch C Azithromycin combination therapy with artesunate or quinine for the treatmentof uncomplicated Plasmodium falciparum malaria in adults a randomized phase 2 clinical trial in Thailand Clin Infect Dis 2006 Nov1543(10)1264shy71 Epub 2006 Oct 12 Pubmed (httpwwwncbinlmnihgovpubmed17051490)
External Links Resource Link
KEGG Compound C06838 (httpwwwgenomejpdbgetshybinwww_bgetcpdC06838)
BindingDB 50197040 (httpwwwbindingdborgbindchemsearchmarvinMolStructurejspmonomerid=50197040)
ChEBI 2955 (httpwwwebiacukchebisearchIddochebiId=2955)
ChEMBL CHEMBL529 (httpwwwebiacukchembldbindexphpcompoundinspectCHEMBL529)
Therapeutic Targets Database DNC001539 (httpbiddnusedusggroupcjttdZFTTDDRUGaspID=DNC001539)
PharmGKB PA448519 (httpwwwpharmgkborgdrugPA448519)
HET ZIT (httpwwwebiacukmsdshysrvchempdbcgishybincgiplFUNCTION=getByCodeampCODE=ZIT)
RxList httpwwwrxlistcomcgigenericzithromaxhtm (httpwwwrxlistcomcgigenericzithromaxhtm)
Drugscom httpwwwdrugscomcdiazithromycinshydropshtml (httpwwwdrugscomcdiazithromycinshydropshtml)
Wikipedia Azithromycin (httpenwikipediaorgwikiAzithromycin)
ATC Codes J01FA10J mdash ANTIINFECTIVES FOR SYSTEMIC USE (atcJJ)J01 mdash ANTIBACTERIALS FOR SYSTEMIC USE (atcJ01J01)J01F mdash MACROLIDES LINCOSAMIDES AND STREPTOGRAMINS (atcJ01FJ01F)J01FA mdash Macrolides (atcJ01FAJ01FA)
S01AA26S mdash SENSORY ORGANS (atcSS)S01 mdash OPHTHALMOLOGICALS (atcS01S01)S01A mdash ANTIINFECTIVES (atcS01AS01A)S01AA mdash Antibiotics (atcS01AAS01AA)
AHFS Codes 08121292
PDB Entries Not Available
FDA label Download (systemfda_labelsDB00207pdf1265922797) (763 KB)
MSDS Download (systemmsdsDB00207pdf1265922737) (739 KB)
Interactions
Drug Interactions Drug
Acenocoumarol(drugsDB01418)
Azithromycin may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration
Anisindione (drugsDB01125) Azithromycin may increase the anticoagulant effect of anisindione by increasing its serum concentration
Artemether (drugsDB06697) Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Cyclosporine(drugsDB00091)
The macrolide azithromycin may increase the effect of cyclosporine
Dicoumarol (drugsDB00266) Azithromycin may increase the anticoagulant effect of dicumarol by increasing its serum concentration
Disopyramide(drugsDB00280)
The macrolide azithromycin may increase the effect of disopyramide
Lovastatin (drugsDB00227) The macrolide antibiotic azithromycin may increase the serum concentration of lovastatin by decreasing its metabolismMonitor for changes in the therapeutic and adverse effects of lovastatin if azithromycin is initiated discontinued or dosechanged
Lumefantrine(drugsDB06708)
Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Vismodegib (drugsDB08828) Pshyglycoprotein inhibitors may increase the chance of adverse drug reactions
Vorinostat (drugsDB02546) Additive QTc prolongation may occur Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsadede Pointes (TdP)
Warfarin (drugsDB00682) Azithromycin may increase the anticoagulant effect of warfarin by increasing its serum concentration
Ziprasidone (drugsDB00246) Additive QTcshyprolonging effects may increase the risk of severe arrhythmias Concomitant therapy is contraindicated
Zuclopenthixol(drugsDB01624)
Additive QTc prolongation may occur Consider alternate therapy or use caution and monitor for QTc prolongation as this canlead to Torsade de Pointes (TdP)
Food Interactions Do not take Aluminum or magnesium antacids or supplements while on this medication
1431753131298898 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 912
Take on empty stomach 1 hour before or 2 hours after meals
Targets
1 23S rRNA (biodbbio_entitiesBE0004800)
Kind nucleotide
Organism Enteric bacteria and other eubacteria
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
References1 Ng LK Martin I Liu G Bryden L Mutation in 23S rRNA associated with macrolide resistance in Neisseria gonorrhoeae Antimicrob Agents Chemother 2002 Sep46(9)3020shy5
Pubmed (httpwwwncbinlmnihgovpubmed12183262)2 Jalava J Vaara M Huovinen P Mutation at the position 2058 of the 23S rRNA as a cause of macrolide resistance in Streptococcus pyogenes Ann Clin Microbiol Antimicrob
2004 May 635 Pubmed (httpwwwncbinlmnihgovpubmed15128458)3 Pereyre S Renaudin H Charron A Bebear C Bebear CM Emergence of a 23S rRNA mutation in Mycoplasma hominis associated with a loss of the intrinsic resistance to
erythromycin and azithromycin J Antimicrob Chemother 2006 Apr57(4)753shy6 Epub 2006 Feb 7 Pubmed (httpwwwncbinlmnihgovpubmed16464889)
2 50S ribosomal protein L4 (biodbbio_entitiesBE0002465)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L4 P60725 (httpwwwuniprotorguniprotP60725) Details (biodbpolypeptidesP60725)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr
22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003
Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan
30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy
24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
3 50S ribosomal protein L22 (biodbbio_entitiesBE0002464)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L22 P61177 (httpwwwuniprotorguniprotP61177) Details (biodbpolypeptidesP61177)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)
1431753131328023 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1012
2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)
3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)
4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)
5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
Enzymes
1 Cytochrome P450 2A6 (biodbbio_entitiesBE0003336)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 2A6 P11509 (httpwwwuniprotorguniprotP11509) Details (biodbpolypeptidesP11509)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
2 Cytochrome P450 3A4 (biodbbio_entitiesBE0002638)
Kind protein
Organism Human
Pharmacological action unknown
Actions substrate inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A4 P08684 (httpwwwuniprotorguniprotP08684) Details (biodbpolypeptidesP08684)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
3 Cytochrome P450 1A2 (biodbbio_entitiesBE0002433)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 1A2 P05177 (httpwwwuniprotorguniprotP05177) Details (biodbpolypeptidesP05177)
References1 Lexicomp
1431753131353312 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1112
(httpwwwcihrshyirscgcca) (httpwwwmetabolomicscentreca)
Transporters
1 Multidrug resistance protein 1 (biodbbio_entitiesBE0001032)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Multidrug resistance protein 1 P08183 (httpwwwuniprotorguniprotP08183) Details (biodbpolypeptidesP08183)
References1 Wang E Lew K Barecki M Casciano CN Clement RP Johnson WW Quantitative distinctions of active site molecular recognition by Pshyglycoprotein and cytochrome P450 3A4
Chem Res Toxicol 2001 Dec14(12)1596shy603 Pubmed (httpwwwncbinlmnihgovpubmed11743742)2 Asakura E Nakayama H Sugie M Zhao YL Nadai M Kitaichi K Shimizu A Miyoshi M Takagi K Takagi K Hasegawa T Azithromycin reverses anticancer drug resistance and
modifies hepatobiliary excretion of doxorubicin in rats Eur J Pharmacol 2004 Jan 26484(2shy3)333shy9 Pubmed (httpwwwncbinlmnihgovpubmed14744620)
Comments
Abiraterone (DB05812)4 comments bull 2 years ago
Adam Maciejewski mdash Hi PangPangGun Thanks for your questionCurrently we dont have this feature but please look at our currentpharmacoeconomics section for information regarding pricesmanufacturers packagers and dosages Thank you Adam
Denosumab (DB06643)1 comment bull 2 years ago
Glenn Pilkington mdash Tsequences you have listed are different to thepatent (WO 2013181575 A2) sequences and the heavy chain sequenceis for a hIgG1 not hIgG2
LYMshy2 (DB05788)2 comments bull a year ago
Adam Maciejewski mdash Hi Nie Lun thank you for letting us know about thisI have created a biotech entry for LYMshy2 and have merged the twodrugs Please see DB09025 Thank you
FTY 720 (DB05286)2 comments bull a year ago
Adam Maciejewski mdash Hello Daniel Himmelstein thank you for pointingthis out Indeed FTY720 is the same drug as the later approvedFingolimod I will merge the two entries into DB08868 If you have anyfurther questions or comments please dont hesitate to hellip
ALSO ON DRUGBANK
2 Comments DrugBank Login1
Share Sort by Best
Join the discussionhellip
bull Reply bull
Bmorale2 bull 3 years ago
I think the Spanish version of this should be translated to Azitromicina not as it shows as Aritromicina
bull Reply bull
Craig Knox bull 3 years agoMod gt Bmorale2
Hi thanks for the tip looks like it was a spelling error Ive corrected it 1
WHATS THIS
Subscribe Add Disqus to your sited Privacy
Recommend 7
Share rsaquo
Share rsaquo
Drug created on June 13 2005 0724 Updated on September 16 2013 1708
1431753133823464 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1212
(httpwwwaihealthsolutionsca) (httpgenomealbertaca) (httpgenomebcca)
(httpgenomecanadaca)
This project is supported by the Canadian Institutes of Health Research (httpwwwcihrshyirscgcca) (award 111062) Alberta Innovates shy Health Solutions(httpwwwaihealthsolutionsca) and by The Metabolomics Innovation Centre (TMIC) (httpwwwmetabolomicscentreca) a nationallyshyfunded research and corefacility that supports a wide range of cuttingshyedge metabolomic studies TMIC is funded by Genome Alberta (httpwwwgenomealbertaca) Genome British Columbia(httpwwwgenomebcca) and Genome Canada (httpwwwgenomecanadaca) a notshyforshyprofit organization that is leading Canadas national genomics strategy with$900 million in funding from the federal government
DrugBank Version 42 mdash Contact Us (httpdrugbankwcontact)
1431753131233812 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 712
Azithromycin 6 250 mg tablet Disp Pack 4852USD disp
Azithromycin 600 mg tablet 1904USD tablet
Azithromycin iv 500 mg vial 1109USD each
DrugBank does not sell nor buy drugs Pricing information is supplied for informational purposes only
Patents
Country Patent Number Approved Expires (estimated)
Canada 2148071 2000shy10shy17 2015shy04shy27
Canada 2467611 2010shy03shy30 2024shy05shy18
United States 5192535 1993shy03shy09 2010shy03shy09
United States 6984403 2004shy02shy14 2024shy02shy14
Properties
State Solid
ExperimentalProperties
Property Value Source
melting point 114 degC PhysProp
water solubility slight Not Available
logP 402 MCFARLANDJW ET AL (1997)
pKa 874 (at 25 degC) MCFARLANDJW ET AL (1997)
PredictedProperties
Property Value Source
Water Solubility 0514 mgmL ALOGPS (httpwwwvcclaborglabalogps)
logP 303 ALOGPS (httpwwwvcclaborglabalogps)
logP 244 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorslogp_logd)
logS shy32 ALOGPS (httpwwwvcclaborglabalogps)
pKa (Strongest Acidic) 1243 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
pKa (Strongest Basic) 957 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Physiological Charge 2 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshypredictorspka)
Hydrogen Acceptor Count 13 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Hydrogen Donor Count 5 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsh_bond)
Polar Surface Area 18008 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopolgical_surface)
Rotatable Bond Count 7 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Refractivity 19411 m middotmol ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationsrefractivity)
Polarizability 8311 Aring ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Number of Rings 3 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginspropertyshycalculationstopology_analysis)
Bioavailability 0 ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Rule of Five Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Ghose Filter Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Vebers Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
MDDRshylike Rule Yes ChemAxon (httpwwwchemaxoncomproductscalculatorshypluginsmolecularshymodellingpolarization)
Spectra
Mass Spec (NIST) Not Available
Spectra Not Available
References
SynthesisReference
William Heggie Zita Maria De Mouro Vaz Azevedo Mendes ldquoProcess for the preparation of azithromycinrdquo US Patent US6013778 issuedNovember 1994
Showing 1 to 10 of 45 entries Previous 2 3 4 5 Next
Show10
entries
Search
Showing 1 to 4 of 4 entries Previous Next
2
3 shy1
3
1
1
1431753131264765 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 812
US6013778 (httpswwwgooglecomtbm=ptsq=6013778amptbm=pts)
General Reference 1 Noedl H Krudsood S Chalermratana K Silachamroon U Leowattana W Tangpukdee N Looareesuwan S Miller RS Fukuda M JongsakulK Sriwichai S Rowan J Bhattacharyya H Ohrt C Knirsch C Azithromycin combination therapy with artesunate or quinine for the treatmentof uncomplicated Plasmodium falciparum malaria in adults a randomized phase 2 clinical trial in Thailand Clin Infect Dis 2006 Nov1543(10)1264shy71 Epub 2006 Oct 12 Pubmed (httpwwwncbinlmnihgovpubmed17051490)
External Links Resource Link
KEGG Compound C06838 (httpwwwgenomejpdbgetshybinwww_bgetcpdC06838)
BindingDB 50197040 (httpwwwbindingdborgbindchemsearchmarvinMolStructurejspmonomerid=50197040)
ChEBI 2955 (httpwwwebiacukchebisearchIddochebiId=2955)
ChEMBL CHEMBL529 (httpwwwebiacukchembldbindexphpcompoundinspectCHEMBL529)
Therapeutic Targets Database DNC001539 (httpbiddnusedusggroupcjttdZFTTDDRUGaspID=DNC001539)
PharmGKB PA448519 (httpwwwpharmgkborgdrugPA448519)
HET ZIT (httpwwwebiacukmsdshysrvchempdbcgishybincgiplFUNCTION=getByCodeampCODE=ZIT)
RxList httpwwwrxlistcomcgigenericzithromaxhtm (httpwwwrxlistcomcgigenericzithromaxhtm)
Drugscom httpwwwdrugscomcdiazithromycinshydropshtml (httpwwwdrugscomcdiazithromycinshydropshtml)
Wikipedia Azithromycin (httpenwikipediaorgwikiAzithromycin)
ATC Codes J01FA10J mdash ANTIINFECTIVES FOR SYSTEMIC USE (atcJJ)J01 mdash ANTIBACTERIALS FOR SYSTEMIC USE (atcJ01J01)J01F mdash MACROLIDES LINCOSAMIDES AND STREPTOGRAMINS (atcJ01FJ01F)J01FA mdash Macrolides (atcJ01FAJ01FA)
S01AA26S mdash SENSORY ORGANS (atcSS)S01 mdash OPHTHALMOLOGICALS (atcS01S01)S01A mdash ANTIINFECTIVES (atcS01AS01A)S01AA mdash Antibiotics (atcS01AAS01AA)
AHFS Codes 08121292
PDB Entries Not Available
FDA label Download (systemfda_labelsDB00207pdf1265922797) (763 KB)
MSDS Download (systemmsdsDB00207pdf1265922737) (739 KB)
Interactions
Drug Interactions Drug
Acenocoumarol(drugsDB01418)
Azithromycin may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration
Anisindione (drugsDB01125) Azithromycin may increase the anticoagulant effect of anisindione by increasing its serum concentration
Artemether (drugsDB06697) Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Cyclosporine(drugsDB00091)
The macrolide azithromycin may increase the effect of cyclosporine
Dicoumarol (drugsDB00266) Azithromycin may increase the anticoagulant effect of dicumarol by increasing its serum concentration
Disopyramide(drugsDB00280)
The macrolide azithromycin may increase the effect of disopyramide
Lovastatin (drugsDB00227) The macrolide antibiotic azithromycin may increase the serum concentration of lovastatin by decreasing its metabolismMonitor for changes in the therapeutic and adverse effects of lovastatin if azithromycin is initiated discontinued or dosechanged
Lumefantrine(drugsDB06708)
Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Vismodegib (drugsDB08828) Pshyglycoprotein inhibitors may increase the chance of adverse drug reactions
Vorinostat (drugsDB02546) Additive QTc prolongation may occur Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsadede Pointes (TdP)
Warfarin (drugsDB00682) Azithromycin may increase the anticoagulant effect of warfarin by increasing its serum concentration
Ziprasidone (drugsDB00246) Additive QTcshyprolonging effects may increase the risk of severe arrhythmias Concomitant therapy is contraindicated
Zuclopenthixol(drugsDB01624)
Additive QTc prolongation may occur Consider alternate therapy or use caution and monitor for QTc prolongation as this canlead to Torsade de Pointes (TdP)
Food Interactions Do not take Aluminum or magnesium antacids or supplements while on this medication
1431753131298898 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 912
Take on empty stomach 1 hour before or 2 hours after meals
Targets
1 23S rRNA (biodbbio_entitiesBE0004800)
Kind nucleotide
Organism Enteric bacteria and other eubacteria
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
References1 Ng LK Martin I Liu G Bryden L Mutation in 23S rRNA associated with macrolide resistance in Neisseria gonorrhoeae Antimicrob Agents Chemother 2002 Sep46(9)3020shy5
Pubmed (httpwwwncbinlmnihgovpubmed12183262)2 Jalava J Vaara M Huovinen P Mutation at the position 2058 of the 23S rRNA as a cause of macrolide resistance in Streptococcus pyogenes Ann Clin Microbiol Antimicrob
2004 May 635 Pubmed (httpwwwncbinlmnihgovpubmed15128458)3 Pereyre S Renaudin H Charron A Bebear C Bebear CM Emergence of a 23S rRNA mutation in Mycoplasma hominis associated with a loss of the intrinsic resistance to
erythromycin and azithromycin J Antimicrob Chemother 2006 Apr57(4)753shy6 Epub 2006 Feb 7 Pubmed (httpwwwncbinlmnihgovpubmed16464889)
2 50S ribosomal protein L4 (biodbbio_entitiesBE0002465)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L4 P60725 (httpwwwuniprotorguniprotP60725) Details (biodbpolypeptidesP60725)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr
22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003
Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan
30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy
24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
3 50S ribosomal protein L22 (biodbbio_entitiesBE0002464)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L22 P61177 (httpwwwuniprotorguniprotP61177) Details (biodbpolypeptidesP61177)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)
1431753131328023 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1012
2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)
3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)
4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)
5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
Enzymes
1 Cytochrome P450 2A6 (biodbbio_entitiesBE0003336)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 2A6 P11509 (httpwwwuniprotorguniprotP11509) Details (biodbpolypeptidesP11509)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
2 Cytochrome P450 3A4 (biodbbio_entitiesBE0002638)
Kind protein
Organism Human
Pharmacological action unknown
Actions substrate inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A4 P08684 (httpwwwuniprotorguniprotP08684) Details (biodbpolypeptidesP08684)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
3 Cytochrome P450 1A2 (biodbbio_entitiesBE0002433)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 1A2 P05177 (httpwwwuniprotorguniprotP05177) Details (biodbpolypeptidesP05177)
References1 Lexicomp
1431753131353312 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1112
(httpwwwcihrshyirscgcca) (httpwwwmetabolomicscentreca)
Transporters
1 Multidrug resistance protein 1 (biodbbio_entitiesBE0001032)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Multidrug resistance protein 1 P08183 (httpwwwuniprotorguniprotP08183) Details (biodbpolypeptidesP08183)
References1 Wang E Lew K Barecki M Casciano CN Clement RP Johnson WW Quantitative distinctions of active site molecular recognition by Pshyglycoprotein and cytochrome P450 3A4
Chem Res Toxicol 2001 Dec14(12)1596shy603 Pubmed (httpwwwncbinlmnihgovpubmed11743742)2 Asakura E Nakayama H Sugie M Zhao YL Nadai M Kitaichi K Shimizu A Miyoshi M Takagi K Takagi K Hasegawa T Azithromycin reverses anticancer drug resistance and
modifies hepatobiliary excretion of doxorubicin in rats Eur J Pharmacol 2004 Jan 26484(2shy3)333shy9 Pubmed (httpwwwncbinlmnihgovpubmed14744620)
Comments
Abiraterone (DB05812)4 comments bull 2 years ago
Adam Maciejewski mdash Hi PangPangGun Thanks for your questionCurrently we dont have this feature but please look at our currentpharmacoeconomics section for information regarding pricesmanufacturers packagers and dosages Thank you Adam
Denosumab (DB06643)1 comment bull 2 years ago
Glenn Pilkington mdash Tsequences you have listed are different to thepatent (WO 2013181575 A2) sequences and the heavy chain sequenceis for a hIgG1 not hIgG2
LYMshy2 (DB05788)2 comments bull a year ago
Adam Maciejewski mdash Hi Nie Lun thank you for letting us know about thisI have created a biotech entry for LYMshy2 and have merged the twodrugs Please see DB09025 Thank you
FTY 720 (DB05286)2 comments bull a year ago
Adam Maciejewski mdash Hello Daniel Himmelstein thank you for pointingthis out Indeed FTY720 is the same drug as the later approvedFingolimod I will merge the two entries into DB08868 If you have anyfurther questions or comments please dont hesitate to hellip
ALSO ON DRUGBANK
2 Comments DrugBank Login1
Share Sort by Best
Join the discussionhellip
bull Reply bull
Bmorale2 bull 3 years ago
I think the Spanish version of this should be translated to Azitromicina not as it shows as Aritromicina
bull Reply bull
Craig Knox bull 3 years agoMod gt Bmorale2
Hi thanks for the tip looks like it was a spelling error Ive corrected it 1
WHATS THIS
Subscribe Add Disqus to your sited Privacy
Recommend 7
Share rsaquo
Share rsaquo
Drug created on June 13 2005 0724 Updated on September 16 2013 1708
1431753133823464 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1212
(httpwwwaihealthsolutionsca) (httpgenomealbertaca) (httpgenomebcca)
(httpgenomecanadaca)
This project is supported by the Canadian Institutes of Health Research (httpwwwcihrshyirscgcca) (award 111062) Alberta Innovates shy Health Solutions(httpwwwaihealthsolutionsca) and by The Metabolomics Innovation Centre (TMIC) (httpwwwmetabolomicscentreca) a nationallyshyfunded research and corefacility that supports a wide range of cuttingshyedge metabolomic studies TMIC is funded by Genome Alberta (httpwwwgenomealbertaca) Genome British Columbia(httpwwwgenomebcca) and Genome Canada (httpwwwgenomecanadaca) a notshyforshyprofit organization that is leading Canadas national genomics strategy with$900 million in funding from the federal government
DrugBank Version 42 mdash Contact Us (httpdrugbankwcontact)
1431753131264765 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 812
US6013778 (httpswwwgooglecomtbm=ptsq=6013778amptbm=pts)
General Reference 1 Noedl H Krudsood S Chalermratana K Silachamroon U Leowattana W Tangpukdee N Looareesuwan S Miller RS Fukuda M JongsakulK Sriwichai S Rowan J Bhattacharyya H Ohrt C Knirsch C Azithromycin combination therapy with artesunate or quinine for the treatmentof uncomplicated Plasmodium falciparum malaria in adults a randomized phase 2 clinical trial in Thailand Clin Infect Dis 2006 Nov1543(10)1264shy71 Epub 2006 Oct 12 Pubmed (httpwwwncbinlmnihgovpubmed17051490)
External Links Resource Link
KEGG Compound C06838 (httpwwwgenomejpdbgetshybinwww_bgetcpdC06838)
BindingDB 50197040 (httpwwwbindingdborgbindchemsearchmarvinMolStructurejspmonomerid=50197040)
ChEBI 2955 (httpwwwebiacukchebisearchIddochebiId=2955)
ChEMBL CHEMBL529 (httpwwwebiacukchembldbindexphpcompoundinspectCHEMBL529)
Therapeutic Targets Database DNC001539 (httpbiddnusedusggroupcjttdZFTTDDRUGaspID=DNC001539)
PharmGKB PA448519 (httpwwwpharmgkborgdrugPA448519)
HET ZIT (httpwwwebiacukmsdshysrvchempdbcgishybincgiplFUNCTION=getByCodeampCODE=ZIT)
RxList httpwwwrxlistcomcgigenericzithromaxhtm (httpwwwrxlistcomcgigenericzithromaxhtm)
Drugscom httpwwwdrugscomcdiazithromycinshydropshtml (httpwwwdrugscomcdiazithromycinshydropshtml)
Wikipedia Azithromycin (httpenwikipediaorgwikiAzithromycin)
ATC Codes J01FA10J mdash ANTIINFECTIVES FOR SYSTEMIC USE (atcJJ)J01 mdash ANTIBACTERIALS FOR SYSTEMIC USE (atcJ01J01)J01F mdash MACROLIDES LINCOSAMIDES AND STREPTOGRAMINS (atcJ01FJ01F)J01FA mdash Macrolides (atcJ01FAJ01FA)
S01AA26S mdash SENSORY ORGANS (atcSS)S01 mdash OPHTHALMOLOGICALS (atcS01S01)S01A mdash ANTIINFECTIVES (atcS01AS01A)S01AA mdash Antibiotics (atcS01AAS01AA)
AHFS Codes 08121292
PDB Entries Not Available
FDA label Download (systemfda_labelsDB00207pdf1265922797) (763 KB)
MSDS Download (systemmsdsDB00207pdf1265922737) (739 KB)
Interactions
Drug Interactions Drug
Acenocoumarol(drugsDB01418)
Azithromycin may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration
Anisindione (drugsDB01125) Azithromycin may increase the anticoagulant effect of anisindione by increasing its serum concentration
Artemether (drugsDB06697) Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Cyclosporine(drugsDB00091)
The macrolide azithromycin may increase the effect of cyclosporine
Dicoumarol (drugsDB00266) Azithromycin may increase the anticoagulant effect of dicumarol by increasing its serum concentration
Disopyramide(drugsDB00280)
The macrolide azithromycin may increase the effect of disopyramide
Lovastatin (drugsDB00227) The macrolide antibiotic azithromycin may increase the serum concentration of lovastatin by decreasing its metabolismMonitor for changes in the therapeutic and adverse effects of lovastatin if azithromycin is initiated discontinued or dosechanged
Lumefantrine(drugsDB06708)
Additive QTcshyprolongation may occur Concomitant therapy should be avoided
Vismodegib (drugsDB08828) Pshyglycoprotein inhibitors may increase the chance of adverse drug reactions
Vorinostat (drugsDB02546) Additive QTc prolongation may occur Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsadede Pointes (TdP)
Warfarin (drugsDB00682) Azithromycin may increase the anticoagulant effect of warfarin by increasing its serum concentration
Ziprasidone (drugsDB00246) Additive QTcshyprolonging effects may increase the risk of severe arrhythmias Concomitant therapy is contraindicated
Zuclopenthixol(drugsDB01624)
Additive QTc prolongation may occur Consider alternate therapy or use caution and monitor for QTc prolongation as this canlead to Torsade de Pointes (TdP)
Food Interactions Do not take Aluminum or magnesium antacids or supplements while on this medication
1431753131298898 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 912
Take on empty stomach 1 hour before or 2 hours after meals
Targets
1 23S rRNA (biodbbio_entitiesBE0004800)
Kind nucleotide
Organism Enteric bacteria and other eubacteria
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
References1 Ng LK Martin I Liu G Bryden L Mutation in 23S rRNA associated with macrolide resistance in Neisseria gonorrhoeae Antimicrob Agents Chemother 2002 Sep46(9)3020shy5
Pubmed (httpwwwncbinlmnihgovpubmed12183262)2 Jalava J Vaara M Huovinen P Mutation at the position 2058 of the 23S rRNA as a cause of macrolide resistance in Streptococcus pyogenes Ann Clin Microbiol Antimicrob
2004 May 635 Pubmed (httpwwwncbinlmnihgovpubmed15128458)3 Pereyre S Renaudin H Charron A Bebear C Bebear CM Emergence of a 23S rRNA mutation in Mycoplasma hominis associated with a loss of the intrinsic resistance to
erythromycin and azithromycin J Antimicrob Chemother 2006 Apr57(4)753shy6 Epub 2006 Feb 7 Pubmed (httpwwwncbinlmnihgovpubmed16464889)
2 50S ribosomal protein L4 (biodbbio_entitiesBE0002465)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L4 P60725 (httpwwwuniprotorguniprotP60725) Details (biodbpolypeptidesP60725)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr
22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003
Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan
30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy
24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
3 50S ribosomal protein L22 (biodbbio_entitiesBE0002464)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L22 P61177 (httpwwwuniprotorguniprotP61177) Details (biodbpolypeptidesP61177)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)
1431753131328023 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1012
2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)
3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)
4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)
5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
Enzymes
1 Cytochrome P450 2A6 (biodbbio_entitiesBE0003336)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 2A6 P11509 (httpwwwuniprotorguniprotP11509) Details (biodbpolypeptidesP11509)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
2 Cytochrome P450 3A4 (biodbbio_entitiesBE0002638)
Kind protein
Organism Human
Pharmacological action unknown
Actions substrate inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A4 P08684 (httpwwwuniprotorguniprotP08684) Details (biodbpolypeptidesP08684)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
3 Cytochrome P450 1A2 (biodbbio_entitiesBE0002433)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 1A2 P05177 (httpwwwuniprotorguniprotP05177) Details (biodbpolypeptidesP05177)
References1 Lexicomp
1431753131353312 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1112
(httpwwwcihrshyirscgcca) (httpwwwmetabolomicscentreca)
Transporters
1 Multidrug resistance protein 1 (biodbbio_entitiesBE0001032)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Multidrug resistance protein 1 P08183 (httpwwwuniprotorguniprotP08183) Details (biodbpolypeptidesP08183)
References1 Wang E Lew K Barecki M Casciano CN Clement RP Johnson WW Quantitative distinctions of active site molecular recognition by Pshyglycoprotein and cytochrome P450 3A4
Chem Res Toxicol 2001 Dec14(12)1596shy603 Pubmed (httpwwwncbinlmnihgovpubmed11743742)2 Asakura E Nakayama H Sugie M Zhao YL Nadai M Kitaichi K Shimizu A Miyoshi M Takagi K Takagi K Hasegawa T Azithromycin reverses anticancer drug resistance and
modifies hepatobiliary excretion of doxorubicin in rats Eur J Pharmacol 2004 Jan 26484(2shy3)333shy9 Pubmed (httpwwwncbinlmnihgovpubmed14744620)
Comments
Abiraterone (DB05812)4 comments bull 2 years ago
Adam Maciejewski mdash Hi PangPangGun Thanks for your questionCurrently we dont have this feature but please look at our currentpharmacoeconomics section for information regarding pricesmanufacturers packagers and dosages Thank you Adam
Denosumab (DB06643)1 comment bull 2 years ago
Glenn Pilkington mdash Tsequences you have listed are different to thepatent (WO 2013181575 A2) sequences and the heavy chain sequenceis for a hIgG1 not hIgG2
LYMshy2 (DB05788)2 comments bull a year ago
Adam Maciejewski mdash Hi Nie Lun thank you for letting us know about thisI have created a biotech entry for LYMshy2 and have merged the twodrugs Please see DB09025 Thank you
FTY 720 (DB05286)2 comments bull a year ago
Adam Maciejewski mdash Hello Daniel Himmelstein thank you for pointingthis out Indeed FTY720 is the same drug as the later approvedFingolimod I will merge the two entries into DB08868 If you have anyfurther questions or comments please dont hesitate to hellip
ALSO ON DRUGBANK
2 Comments DrugBank Login1
Share Sort by Best
Join the discussionhellip
bull Reply bull
Bmorale2 bull 3 years ago
I think the Spanish version of this should be translated to Azitromicina not as it shows as Aritromicina
bull Reply bull
Craig Knox bull 3 years agoMod gt Bmorale2
Hi thanks for the tip looks like it was a spelling error Ive corrected it 1
WHATS THIS
Subscribe Add Disqus to your sited Privacy
Recommend 7
Share rsaquo
Share rsaquo
Drug created on June 13 2005 0724 Updated on September 16 2013 1708
1431753133823464 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1212
(httpwwwaihealthsolutionsca) (httpgenomealbertaca) (httpgenomebcca)
(httpgenomecanadaca)
This project is supported by the Canadian Institutes of Health Research (httpwwwcihrshyirscgcca) (award 111062) Alberta Innovates shy Health Solutions(httpwwwaihealthsolutionsca) and by The Metabolomics Innovation Centre (TMIC) (httpwwwmetabolomicscentreca) a nationallyshyfunded research and corefacility that supports a wide range of cuttingshyedge metabolomic studies TMIC is funded by Genome Alberta (httpwwwgenomealbertaca) Genome British Columbia(httpwwwgenomebcca) and Genome Canada (httpwwwgenomecanadaca) a notshyforshyprofit organization that is leading Canadas national genomics strategy with$900 million in funding from the federal government
DrugBank Version 42 mdash Contact Us (httpdrugbankwcontact)
1431753131298898 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 912
Take on empty stomach 1 hour before or 2 hours after meals
Targets
1 23S rRNA (biodbbio_entitiesBE0004800)
Kind nucleotide
Organism Enteric bacteria and other eubacteria
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
References1 Ng LK Martin I Liu G Bryden L Mutation in 23S rRNA associated with macrolide resistance in Neisseria gonorrhoeae Antimicrob Agents Chemother 2002 Sep46(9)3020shy5
Pubmed (httpwwwncbinlmnihgovpubmed12183262)2 Jalava J Vaara M Huovinen P Mutation at the position 2058 of the 23S rRNA as a cause of macrolide resistance in Streptococcus pyogenes Ann Clin Microbiol Antimicrob
2004 May 635 Pubmed (httpwwwncbinlmnihgovpubmed15128458)3 Pereyre S Renaudin H Charron A Bebear C Bebear CM Emergence of a 23S rRNA mutation in Mycoplasma hominis associated with a loss of the intrinsic resistance to
erythromycin and azithromycin J Antimicrob Chemother 2006 Apr57(4)753shy6 Epub 2006 Feb 7 Pubmed (httpwwwncbinlmnihgovpubmed16464889)
2 50S ribosomal protein L4 (biodbbio_entitiesBE0002465)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L4 P60725 (httpwwwuniprotorguniprotP60725) Details (biodbpolypeptidesP60725)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr
22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003
Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan
30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy
24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
3 50S ribosomal protein L22 (biodbbio_entitiesBE0002464)
Kind protein
Organism Escherichia coli O157H7
Pharmacological action yes
Actions inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L22 P61177 (httpwwwuniprotorguniprotP61177) Details (biodbpolypeptidesP61177)
References1 Halling SM Jensen AE Intrinsic and selected resistance to antibiotics binding the ribosome analyses of Brucella 23S rrn L4 L22 EFshyTu1 EFshyTu2 efflux and phylogenetic
implications BMC Microbiol 2006 Oct 2684 Pubmed (httpwwwncbinlmnihgovpubmed17014718)
1431753131328023 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1012
2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)
3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)
4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)
5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
Enzymes
1 Cytochrome P450 2A6 (biodbbio_entitiesBE0003336)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 2A6 P11509 (httpwwwuniprotorguniprotP11509) Details (biodbpolypeptidesP11509)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
2 Cytochrome P450 3A4 (biodbbio_entitiesBE0002638)
Kind protein
Organism Human
Pharmacological action unknown
Actions substrate inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A4 P08684 (httpwwwuniprotorguniprotP08684) Details (biodbpolypeptidesP08684)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
3 Cytochrome P450 1A2 (biodbbio_entitiesBE0002433)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 1A2 P05177 (httpwwwuniprotorguniprotP05177) Details (biodbpolypeptidesP05177)
References1 Lexicomp
1431753131353312 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1112
(httpwwwcihrshyirscgcca) (httpwwwmetabolomicscentreca)
Transporters
1 Multidrug resistance protein 1 (biodbbio_entitiesBE0001032)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Multidrug resistance protein 1 P08183 (httpwwwuniprotorguniprotP08183) Details (biodbpolypeptidesP08183)
References1 Wang E Lew K Barecki M Casciano CN Clement RP Johnson WW Quantitative distinctions of active site molecular recognition by Pshyglycoprotein and cytochrome P450 3A4
Chem Res Toxicol 2001 Dec14(12)1596shy603 Pubmed (httpwwwncbinlmnihgovpubmed11743742)2 Asakura E Nakayama H Sugie M Zhao YL Nadai M Kitaichi K Shimizu A Miyoshi M Takagi K Takagi K Hasegawa T Azithromycin reverses anticancer drug resistance and
modifies hepatobiliary excretion of doxorubicin in rats Eur J Pharmacol 2004 Jan 26484(2shy3)333shy9 Pubmed (httpwwwncbinlmnihgovpubmed14744620)
Comments
Abiraterone (DB05812)4 comments bull 2 years ago
Adam Maciejewski mdash Hi PangPangGun Thanks for your questionCurrently we dont have this feature but please look at our currentpharmacoeconomics section for information regarding pricesmanufacturers packagers and dosages Thank you Adam
Denosumab (DB06643)1 comment bull 2 years ago
Glenn Pilkington mdash Tsequences you have listed are different to thepatent (WO 2013181575 A2) sequences and the heavy chain sequenceis for a hIgG1 not hIgG2
LYMshy2 (DB05788)2 comments bull a year ago
Adam Maciejewski mdash Hi Nie Lun thank you for letting us know about thisI have created a biotech entry for LYMshy2 and have merged the twodrugs Please see DB09025 Thank you
FTY 720 (DB05286)2 comments bull a year ago
Adam Maciejewski mdash Hello Daniel Himmelstein thank you for pointingthis out Indeed FTY720 is the same drug as the later approvedFingolimod I will merge the two entries into DB08868 If you have anyfurther questions or comments please dont hesitate to hellip
ALSO ON DRUGBANK
2 Comments DrugBank Login1
Share Sort by Best
Join the discussionhellip
bull Reply bull
Bmorale2 bull 3 years ago
I think the Spanish version of this should be translated to Azitromicina not as it shows as Aritromicina
bull Reply bull
Craig Knox bull 3 years agoMod gt Bmorale2
Hi thanks for the tip looks like it was a spelling error Ive corrected it 1
WHATS THIS
Subscribe Add Disqus to your sited Privacy
Recommend 7
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Drug created on June 13 2005 0724 Updated on September 16 2013 1708
1431753133823464 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1212
(httpwwwaihealthsolutionsca) (httpgenomealbertaca) (httpgenomebcca)
(httpgenomecanadaca)
This project is supported by the Canadian Institutes of Health Research (httpwwwcihrshyirscgcca) (award 111062) Alberta Innovates shy Health Solutions(httpwwwaihealthsolutionsca) and by The Metabolomics Innovation Centre (TMIC) (httpwwwmetabolomicscentreca) a nationallyshyfunded research and corefacility that supports a wide range of cuttingshyedge metabolomic studies TMIC is funded by Genome Alberta (httpwwwgenomealbertaca) Genome British Columbia(httpwwwgenomebcca) and Genome Canada (httpwwwgenomecanadaca) a notshyforshyprofit organization that is leading Canadas national genomics strategy with$900 million in funding from the federal government
DrugBank Version 42 mdash Contact Us (httpdrugbankwcontact)
1431753131328023 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1012
2 Tu D Blaha G Moore PB Steitz TA Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance Cell 2005 Apr22121(2)257shy70 Pubmed (httpwwwncbinlmnihgovpubmed15851032)
3 Schlunzen F Harms JM Franceschi F Hansen HA Bartels H Zarivach R Yonath A Structural basis for the antibiotic activity of ketolides and azalides Structure 2003Mar11(3)329shy38 Pubmed (httpwwwncbinlmnihgovpubmed12623020)
4 Petropoulos AD Kouvela EC Starosta AL Wilson DN Dinos GP Kalpaxis DL Timeshyresolved binding of azithromycin to Escherichia coli ribosomes J Mol Biol 2009 Jan30385(4)1179shy92 Epub 2008 Nov 27 Pubmed (httpwwwncbinlmnihgovpubmed19071138)
5 Champney WS Miller M Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin Curr Microbiol 2002 Jun44(6)418shy24 Pubmed (httpwwwncbinlmnihgovpubmed12000992)
Enzymes
1 Cytochrome P450 2A6 (biodbbio_entitiesBE0003336)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 2A6 P11509 (httpwwwuniprotorguniprotP11509) Details (biodbpolypeptidesP11509)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
2 Cytochrome P450 3A4 (biodbbio_entitiesBE0002638)
Kind protein
Organism Human
Pharmacological action unknown
Actions substrate inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A4 P08684 (httpwwwuniprotorguniprotP08684) Details (biodbpolypeptidesP08684)
References1 Preissner S Kroll K Dunkel M Senger C Goldsobel G Kuzman D Guenther S Winnenburg R Schroeder M Preissner R SuperCYP a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYPshydrug interactions Nucleic Acids Res 2010 Jan38(Database issue)D237shy43 Epub 2009 Nov 24 Pubmed(httpwwwncbinlmnihgovpubmed19934256)
3 Cytochrome P450 1A2 (biodbbio_entitiesBE0002433)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Cytochrome P450 1A2 P05177 (httpwwwuniprotorguniprotP05177) Details (biodbpolypeptidesP05177)
References1 Lexicomp
1431753131353312 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1112
(httpwwwcihrshyirscgcca) (httpwwwmetabolomicscentreca)
Transporters
1 Multidrug resistance protein 1 (biodbbio_entitiesBE0001032)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Multidrug resistance protein 1 P08183 (httpwwwuniprotorguniprotP08183) Details (biodbpolypeptidesP08183)
References1 Wang E Lew K Barecki M Casciano CN Clement RP Johnson WW Quantitative distinctions of active site molecular recognition by Pshyglycoprotein and cytochrome P450 3A4
Chem Res Toxicol 2001 Dec14(12)1596shy603 Pubmed (httpwwwncbinlmnihgovpubmed11743742)2 Asakura E Nakayama H Sugie M Zhao YL Nadai M Kitaichi K Shimizu A Miyoshi M Takagi K Takagi K Hasegawa T Azithromycin reverses anticancer drug resistance and
modifies hepatobiliary excretion of doxorubicin in rats Eur J Pharmacol 2004 Jan 26484(2shy3)333shy9 Pubmed (httpwwwncbinlmnihgovpubmed14744620)
Comments
Abiraterone (DB05812)4 comments bull 2 years ago
Adam Maciejewski mdash Hi PangPangGun Thanks for your questionCurrently we dont have this feature but please look at our currentpharmacoeconomics section for information regarding pricesmanufacturers packagers and dosages Thank you Adam
Denosumab (DB06643)1 comment bull 2 years ago
Glenn Pilkington mdash Tsequences you have listed are different to thepatent (WO 2013181575 A2) sequences and the heavy chain sequenceis for a hIgG1 not hIgG2
LYMshy2 (DB05788)2 comments bull a year ago
Adam Maciejewski mdash Hi Nie Lun thank you for letting us know about thisI have created a biotech entry for LYMshy2 and have merged the twodrugs Please see DB09025 Thank you
FTY 720 (DB05286)2 comments bull a year ago
Adam Maciejewski mdash Hello Daniel Himmelstein thank you for pointingthis out Indeed FTY720 is the same drug as the later approvedFingolimod I will merge the two entries into DB08868 If you have anyfurther questions or comments please dont hesitate to hellip
ALSO ON DRUGBANK
2 Comments DrugBank Login1
Share Sort by Best
Join the discussionhellip
bull Reply bull
Bmorale2 bull 3 years ago
I think the Spanish version of this should be translated to Azitromicina not as it shows as Aritromicina
bull Reply bull
Craig Knox bull 3 years agoMod gt Bmorale2
Hi thanks for the tip looks like it was a spelling error Ive corrected it 1
WHATS THIS
Subscribe Add Disqus to your sited Privacy
Recommend 7
Share rsaquo
Share rsaquo
Drug created on June 13 2005 0724 Updated on September 16 2013 1708
1431753133823464 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1212
(httpwwwaihealthsolutionsca) (httpgenomealbertaca) (httpgenomebcca)
(httpgenomecanadaca)
This project is supported by the Canadian Institutes of Health Research (httpwwwcihrshyirscgcca) (award 111062) Alberta Innovates shy Health Solutions(httpwwwaihealthsolutionsca) and by The Metabolomics Innovation Centre (TMIC) (httpwwwmetabolomicscentreca) a nationallyshyfunded research and corefacility that supports a wide range of cuttingshyedge metabolomic studies TMIC is funded by Genome Alberta (httpwwwgenomealbertaca) Genome British Columbia(httpwwwgenomebcca) and Genome Canada (httpwwwgenomecanadaca) a notshyforshyprofit organization that is leading Canadas national genomics strategy with$900 million in funding from the federal government
DrugBank Version 42 mdash Contact Us (httpdrugbankwcontact)
1431753131353312 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1112
(httpwwwcihrshyirscgcca) (httpwwwmetabolomicscentreca)
Transporters
1 Multidrug resistance protein 1 (biodbbio_entitiesBE0001032)
Kind protein
Organism Human
Pharmacological action unknown
Actions inhibitor
Components
Name UniProt ID Details
Multidrug resistance protein 1 P08183 (httpwwwuniprotorguniprotP08183) Details (biodbpolypeptidesP08183)
References1 Wang E Lew K Barecki M Casciano CN Clement RP Johnson WW Quantitative distinctions of active site molecular recognition by Pshyglycoprotein and cytochrome P450 3A4
Chem Res Toxicol 2001 Dec14(12)1596shy603 Pubmed (httpwwwncbinlmnihgovpubmed11743742)2 Asakura E Nakayama H Sugie M Zhao YL Nadai M Kitaichi K Shimizu A Miyoshi M Takagi K Takagi K Hasegawa T Azithromycin reverses anticancer drug resistance and
modifies hepatobiliary excretion of doxorubicin in rats Eur J Pharmacol 2004 Jan 26484(2shy3)333shy9 Pubmed (httpwwwncbinlmnihgovpubmed14744620)
Comments
Abiraterone (DB05812)4 comments bull 2 years ago
Adam Maciejewski mdash Hi PangPangGun Thanks for your questionCurrently we dont have this feature but please look at our currentpharmacoeconomics section for information regarding pricesmanufacturers packagers and dosages Thank you Adam
Denosumab (DB06643)1 comment bull 2 years ago
Glenn Pilkington mdash Tsequences you have listed are different to thepatent (WO 2013181575 A2) sequences and the heavy chain sequenceis for a hIgG1 not hIgG2
LYMshy2 (DB05788)2 comments bull a year ago
Adam Maciejewski mdash Hi Nie Lun thank you for letting us know about thisI have created a biotech entry for LYMshy2 and have merged the twodrugs Please see DB09025 Thank you
FTY 720 (DB05286)2 comments bull a year ago
Adam Maciejewski mdash Hello Daniel Himmelstein thank you for pointingthis out Indeed FTY720 is the same drug as the later approvedFingolimod I will merge the two entries into DB08868 If you have anyfurther questions or comments please dont hesitate to hellip
ALSO ON DRUGBANK
2 Comments DrugBank Login1
Share Sort by Best
Join the discussionhellip
bull Reply bull
Bmorale2 bull 3 years ago
I think the Spanish version of this should be translated to Azitromicina not as it shows as Aritromicina
bull Reply bull
Craig Knox bull 3 years agoMod gt Bmorale2
Hi thanks for the tip looks like it was a spelling error Ive corrected it 1
WHATS THIS
Subscribe Add Disqus to your sited Privacy
Recommend 7
Share rsaquo
Share rsaquo
Drug created on June 13 2005 0724 Updated on September 16 2013 1708
1431753133823464 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1212
(httpwwwaihealthsolutionsca) (httpgenomealbertaca) (httpgenomebcca)
(httpgenomecanadaca)
This project is supported by the Canadian Institutes of Health Research (httpwwwcihrshyirscgcca) (award 111062) Alberta Innovates shy Health Solutions(httpwwwaihealthsolutionsca) and by The Metabolomics Innovation Centre (TMIC) (httpwwwmetabolomicscentreca) a nationallyshyfunded research and corefacility that supports a wide range of cuttingshyedge metabolomic studies TMIC is funded by Genome Alberta (httpwwwgenomealbertaca) Genome British Columbia(httpwwwgenomebcca) and Genome Canada (httpwwwgenomecanadaca) a notshyforshyprofit organization that is leading Canadas national genomics strategy with$900 million in funding from the federal government
DrugBank Version 42 mdash Contact Us (httpdrugbankwcontact)
1431753133823464 DrugBank Azithromycin (DB00207)
httpwwwdrugbankcadrugsDB00207 1212
(httpwwwaihealthsolutionsca) (httpgenomealbertaca) (httpgenomebcca)
(httpgenomecanadaca)
This project is supported by the Canadian Institutes of Health Research (httpwwwcihrshyirscgcca) (award 111062) Alberta Innovates shy Health Solutions(httpwwwaihealthsolutionsca) and by The Metabolomics Innovation Centre (TMIC) (httpwwwmetabolomicscentreca) a nationallyshyfunded research and corefacility that supports a wide range of cuttingshyedge metabolomic studies TMIC is funded by Genome Alberta (httpwwwgenomealbertaca) Genome British Columbia(httpwwwgenomebcca) and Genome Canada (httpwwwgenomecanadaca) a notshyforshyprofit organization that is leading Canadas national genomics strategy with$900 million in funding from the federal government
DrugBank Version 42 mdash Contact Us (httpdrugbankwcontact)
