Amoxicilin from Wikipedia

8/8/2019 Amoxicilin from Wikipedia

1/5

Amoxicillin 1

Amoxicillin

Amoxicillin

Systematic (IUPAC) name

(2S,5R,6R)- 6-{[(2R)-2-amino- 2-(4-hydroxyphenyl)- acetyl]amino}- 3,3-dimethyl- 7-oxo- 4-thia- 1-azabicyclo[3.2.0]heptane-

2-carboxylic acid

Identifiers

CAS number 26787-78-0[1]

ATC code J01 CA04[2]

QG51 AX01[3]

PubChem CID 33613[4]

DrugBank DB01060[5]

ChemSpider 31006[6]

Chemical data

Formula C16

H19

N3O

5S

Mol. mass 365.4 g/mol

SMILES eMolecules[7]

& PubChem[8]

Pharmacokinetic data

Bioavailability 95% oral

Metabolism less than 30% biotransformed in liver

Half-life 61.3 minutes

Excretion renal

Therapeutic considerations

Pregnancy cat. A(AU) B(US)

Legal status POM (UK)

Routes Oral, intravenous

(what is this?) (verify)[9]
http://en.wikipedia.org/w/index.php?&diff=cur&oldid=321803860http://en.wikipedia.org/w/index.php?title=Wikipedia:WikiProject_Chemicals/Chembox_validationhttp://en.wikipedia.org/w/index.php?title=File:Yes_check.svghttp://en.wikipedia.org/w/index.php?title=Intravenous_therapyhttp://en.wiktionary.org/wiki/oralhttp://en.wikipedia.org/w/index.php?title=Route_of_administrationhttp://en.wikipedia.org/w/index.php?title=United_Kingdomhttp://en.wikipedia.org/w/index.php?title=Prescription_drughttp://en.wikipedia.org/w/index.php?title=Regulation_of_therapeutic_goodshttp://en.wikipedia.org/w/index.php?title=United_Stateshttp://en.wikipedia.org/w/index.php?title=Australiahttp://en.wikipedia.org/w/index.php?title=Pregnancy_categoryhttp://en.wikipedia.org/w/index.php?title=Renalhttp://en.wikipedia.org/w/index.php?title=Excretionhttp://en.wikipedia.org/w/index.php?title=Biological_half-lifehttp://en.wikipedia.org/w/index.php?title=Liverhttp://en.wikipedia.org/w/index.php?title=Drug_metabolismhttp://en.wikipedia.org/w/index.php?title=Bioavailabilityhttp://pubchem.ncbi.nlm.nih.gov/search/?smarts=O%3DC%28O%29%5BC%40%40H%5D2N3C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29%5BC%40%40H%5D%28c1ccc%28O%29cc1%29N%29%5BC%40H%5D3SC2%28C%29Chttp://www.emolecules.com/cgi-bin/search?t=ex&q=O%3DC%28O%29%5BC%40%40H%5D2N3C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29%5BC%40%40H%5D%28c1ccc%28O%29cc1%29N%29%5BC%40H%5D3SC2%28C%29Chttp://en.wikipedia.org/w/index.php?title=Simplified_molecular_input_line_entry_specificationhttp://en.wikipedia.org/w/index.php?title=Molecular_masshttp://en.wikipedia.org/w/index.php?title=Sulfurhttp://en.wikipedia.org/w/index.php?title=Oxygenhttp://en.wikipedia.org/w/index.php?title=Nitrogenhttp://en.wikipedia.org/w/index.php?title=Hydrogenhttp://en.wikipedia.org/w/index.php?title=Carbonhttp://en.wikipedia.org/w/index.php?title=Chemical_formulahttp://www.chemspider.com/Chemical-Structure.31006http://en.wikipedia.org/w/index.php?title=ChemSpiderhttp://www.drugbank.ca/cgi-bin/show_drug.cgi?CARD=DB01060http://en.wikipedia.org/w/index.php?title=DrugBankhttp://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=33613http://en.wikipedia.org/w/index.php?title=PubChemhttp://www.whocc.no/atcvet/atcvet_index/?code=QG51AX01http://en.wikipedia.org/w/index.php?title=ATCvet_code_QG51http://www.whocc.no/atc_ddd_index/?code=J01CA04http://en.wikipedia.org/w/index.php?title=ATC_code_J01http://en.wikipedia.org/w/index.php?title=Anatomical_Therapeutic_Chemical_Classification_Systemhttp://www.nlm.nih.gov/cgi/mesh/2009/MB_cgi?term=26787-78-0&rn=1http://en.wikipedia.org/w/index.php?title=CAS_registry_numberhttp://en.wikipedia.org/w/index.php?title=International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/w/index.php?title=File:Amoxicillin-3D-balls.pnghttp://en.wikipedia.org/w/index.php?title=File:Amoxicillin.svg


2/5

Amoxicillin 2

Amoxicillin BP

Amoxicillin (INN), formerly amoxycillin (BAN), amoxycillin

(cilamox) in Australia[10]

, abbreviated Amox,Tormoxin (in India), is

a moderate-spectrum, bacteriolytic, -lactam antibiotic used to treat

bacterial infections caused by susceptible microorganisms. It is usually

the drug of choice within the class because it is better absorbed,

following oral administration, than other -lactam antibiotics. It is alsoa treatment for cystic acne.

[11]

Amoxicillin is susceptible to degradation by -lactamase-producing

bacteria, and so may be given with clavulanic acid to decrease its

susceptibility.

Mode of action

Amoxicillin acts by inhibiting the synthesis of bacterial cell wall. It inhibits cross-linkage between the linear

peptidoglycan polymer chains that make up a major component of the cell walls of both Gram-positive andGram-negative bacteria

Formulations

Amoxicillin in trihydrate form is available as capsules, chewable and dispersible tablets plus syrup and pediatric

suspension for oral use, and as the sodium salt for intravenous administration (although the IV formulation is not

available in the United States[12]

). It is one of the most common antibiotics prescribed for children, and the liquid

forms are helpful where the patient might find it difficult to take tablets or capsules. It has three ionizable groups. A

once daily dosing form (Moxatag) was approved by the American FDA in January 2008.

Side effects

Side effects are as those for other beta-lactam antibiotics. Side effects include nausea, vomiting, rashes, and

antibiotic-associated colitis. Loose bowel movements (diarrhea) also may occur. Rarer but patient reported side

effects include mental changes, lightheadedness, confusion, suicidal thoughts, depression, anxiety, sensitivity to

lights and sounds, unclear thinking. Immediate medical care is required upon the first signs of these side effects.

The onset of an allergic reaction to amoxicillin can be very sudden and intense - emergency medical attention must

be sought as quickly as possible. The initial onset of such a reaction often starts with a change in mental state; skin

rash with intense itching (often beginning in fingertips and around groin area and rapidly spreading) and sensations

of fever, nausea, and vomiting. Any other symptoms that seem even remotely suspicious must be taken very

seriously.

Use of the amoxicillin/clavulanic acid combination for more than one week has caused moderate to severe hepatitis

in a number of patients. Young children who ingested acute overdoses of amoxicillin manifested lethargy, vomiting

and renal dysfunction.[13]

[14]
http://en.wikipedia.org/w/index.php?title=Nauseahttp://en.wikipedia.org/w/index.php?title=Beta-lactam_antibiotic%23Adverse_effectshttp://en.wikipedia.org/w/index.php?title=Adverse_drug_reactionhttp://en.wikipedia.org/w/index.php?title=Food_and_Drug_Administration_%28United_States%29http://en.wikipedia.org/w/index.php?title=Ionizablehttp://en.wikipedia.org/w/index.php?title=Antibiotichttp://en.wikipedia.org/w/index.php?title=Intravenoushttp://en.wikipedia.org/w/index.php?title=Pediatricshttp://en.wikipedia.org/w/index.php?title=Hydratehttp://en.wikipedia.org/w/index.php?title=Gram-negative_bacteriahttp://en.wikipedia.org/w/index.php?title=Gram-positive_bacteriahttp://en.wikipedia.org/w/index.php?title=Cell_wallhttp://en.wikipedia.org/w/index.php?title=Cross-linkhttp://en.wikipedia.org/w/index.php?title=Cell_wallhttp://en.wikipedia.org/w/index.php?title=Clavulanic_acidhttp://en.wikipedia.org/w/index.php?title=Beta-lactamasehttp://en.wikipedia.org/w/index.php?title=Microorganismhttp://en.wikipedia.org/w/index.php?title=Infectionhttp://en.wikipedia.org/w/index.php?title=Bacterialhttp://en.wikipedia.org/w/index.php?title=Antibiotichttp://en.wikipedia.org/w/index.php?title=Beta-lactam_antibiotichttp://en.wikipedia.org/w/index.php?title=British_Approved_Namehttp://en.wikipedia.org/w/index.php?title=International_Nonproprietary_Namehttp://en.wikipedia.org/w/index.php?title=File:Amoxicillin.JPG


3/5

Amoxicillin 3

Non-allergic amoxicillin rash

Somewhere between 3% to 10% of children taking amoxicillin (or ampicillin) show a late-developing (>72 hours

after beginning medication and having never taken penicillin-like medication previously) often itchy rash [15][16],

which is sometimes referred to as the "amoxicillin rash." The rash can also occur in adults.

The rash is described as maculopapular or morbilliform (measles-like; therefore, in medical literature,

"amoxicillin-induced morbilliform rash"[17] ). It starts on the trunk and can spread from there. This rash is unlikely to

be a true allergic reaction, and is not a contra-indication for future amoxicillin usage, nor should current regimen

necessarily be stopped. However, as mentioned above, this common amoxicillin rash and a dangerous allergic

reaction cannot easily be distinguished by inexperienced persons, and therefore a health professional should be

consulted if a rash develops. (Pichichero, 2005; Schmitt 2005)

A non-allergic amoxicillin rash may also be an indicator of infectious mononucleosis: Some studies indicate that

approximately 80-90% of patients with acute Epstein Barr virus infection treated with amoxicillin or ampicillin

develop such a rash.[18]

Non-allergic amoxicillin rash 8

days after first dose, 24 hours

after rash began. Diagnosed by

pediatric resident at local

university hospital.

8 hours after first photo. Individual

spots have grown and begun to

merge.

23 hours after first photo. Color apparently

fading, much of rash has spread to

confluence.

Proprietary preparations

Novamoxin Prescription Drug - 500mg

Amoxicillin Trihydrate

Amoxicillin is one of the semi-synthetic penicillins discovered by

Beecham scientists. The patent for amoxicillin has expired, thusamoxicillin is marketed under many trade names, including:',

Actimoxi, Alphamox, Amocla, AMK, Amoksibos, Amoxiclav Sandoz,

Amoxidal, Amoxil, Amoxin, Amoksiklav, Amoxibiotic, Amoxicilina,

Apo-Amoxi, Augmentin (with clavulanic acid), Bactox, Betalaktam,

Cilamox, Curam, Dedoxil, Dispermox, Duomox, E-Mox, Enhancin,

Gimalxina, Geramox, Hiconcil, Isimoxin, Klavox, Lamoxy, Moxatag,

Moxilen, Moxypen, Moxyvit, Nobactam, Novamoxin, Ospamox,

Panklav, Pamoxicillin, Panamox, Polymox, Samthongcillin, Clamoxyl,

Senox, Sinacilin, Trimox, Tolodina, Tormoxin (India), Wymox, Yucla,

Zerrsox and Zimox.
http://en.wikipedia.org/w/index.php?title=Clavulanic_acidhttp://en.wikipedia.org/w/index.php?title=Beecham_%28pharmaceutical_company%29http://en.wikipedia.org/w/index.php?title=File:NOVAMOXIN.JPGhttp://en.wikipedia.org/w/index.php?title=File:Amoxicillin_rash_26_hours_after_17th_dose.JPGhttp://en.wikipedia.org/w/index.php?title=File:Amoxicillin_rash_11_hours_after_17th_dose.JPGhttp://en.wikipedia.org/w/index.php?title=File:Amoxicillin_rash_3_hours_after_17th_dose.JPGhttp://en.wikipedia.org/w/index.php?title=Ampicillinhttp://en.wikipedia.org/w/index.php?title=Epstein_Barr_virushttp://en.wikipedia.org/w/index.php?title=Infectious_mononucleosishttp://en.wikipedia.org/w/index.php?title=Measleshttp://en.wikipedia.org/w/index.php?title=Maculopapularhttp://www.medhelp.org/posts/Allergy/Rash-from-Amoxicillin/show/4008http://forums.wrongdiagnosis.com/showthread.php?t=15875http://en.wikipedia.org/w/index.php?title=Ampicillin


4/5

Amoxicillin 4

References

Middlebrook Pharmaceuticals (March 2009). "MiddleBrook Pharmaceuticals Launches MOXATAG(TM), the

First and Only FDA-Approved Once-Daily Amoxicillin"[19]

.

GlaxoSmithKline (February 2006). "Amoxil - Prescribing information"[20]

(PDF).

Neal, M. J. (2002).Medical pharmacology at a glance (4th ed.). Oxford: Blackwell Science.

ISBN 0-632-05244-9.

Pichichero ME (April 2005). "A review of evidence supporting the American Academy of Pediatrics

recommendation for prescribing cephalosporin antibiotics for penicillin-allergic patients"[21]

.Pediatrics115 (4):

104857. doi:10.1542/peds.2004-1276. PMID 15805383.

Schmitt, Barton D. (2005). Your child's health: the parents' one-stop reference guide to symptoms, emergencies,

common illnesses, behavior problems, healthy development(2nd ed.). New York: Bantam Books.

ISBN 0-553-38369-8.

British National Formulary 45 March 2003

External links

University of Michigan Mott's Children's Hospital article about "amoxicillin rash."[22]

(Very similar to Schmitt

2005 content)

Amoxicillin Side Effect Experiences[23]

U.S. National Library of Medicine: Drug Information Portal - Amoxicillin[24]

References

[1] http://www.nlm. nih.gov/cgi/mesh/2009/MB_cgi?term=26787-78-0&rn=1

[2] http://www.whocc. no/atc_ddd_index/?code=J01CA04

[3] http://www.whocc. no/atcvet/atcvet_index/?code=QG51AX01

[4] http://pubchem.ncbi. nlm.nih.gov/summary/summary.cgi?cid=33613

[5] http://www.drugbank. ca/cgi-bin/show_drug.cgi?CARD=DB01060

[6] http://www.chemspider. com/Chemical-Structure.31006

[7] http://www.emolecules.com/cgi-bin/search?t=ex&

q=O%3DC%28O%29%5BC%40%40H%5D2N3C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29%5BC%40%40H%5D%28c1ccc%28O%29cc1

[8] http://pubchem.ncbi. nlm.nih.gov/search/

?smarts=O%3DC%28O%29%5BC%40%40H%5D2N3C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29%5BC%40%40H%5D%28c1ccc%28O%

[9] http://en. wikipedia. org/w/index. php?&diff=cur&oldid=321803860

[10] (http://www.racgp. org. au/cmi/txcamoxc. pdf), Royal Australian College of General Practitioners Leaflet.

[11] "Adolescent Acne: Management" (http://www.medscape.com/viewarticle/430534_5). .

[12] www.UpToDate.com

[13] Cundiff J, Joe S. Amoxicillin-clavulanic acid-induced hepatitis. Amer. J. Otolaryngol. 28: 28-30, 2007.

[14] R. Baselt,Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 81-83.

[15] http://forums.wrongdiagnosis. com/showthread.php?t=15875

[16] http://www.medhelp. org/posts/Allergy/Rash-from-Amoxicillin/show/4008

[17] e.g.Role of delayed cellular hypersensitivity and adhesion molecules in amoxicillin-induced morbilliform rashes (http://cat. inist.fr/

?aModele=afficheN&cpsidt=2654598)

[18] Kagan, B (1977). "Ampicillin rash" (http://www.pubmedcentral. nih.gov/articlerender. fcgi?artid=1237570). Western Journal of

Medicine126 (4): 333335. PMID 855325. PMC 1237570. .

[19] http://www.middlebrookpharma. com/releasedetail.cfm?ReleaseID=427462

[20] http://us. gsk. com/products/assets/us_amoxil.pdf

[21] http://pediatrics.aappublications.org/cgi/content/full/115/4/1048

[22] http://www.med.umich. edu/1libr/pa/pa_ampirash_hhg.htm

[23] http://www.amoxicillinsideeffects.net/

[24] http://druginfo.nlm. nih.gov/drugportal/dpdirect.jsp?name=Amoxicillin+anhydrous
http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=Amoxicillin+anhydroushttp://www.amoxicillinsideeffects.net/http://www.med.umich.edu/1libr/pa/pa_ampirash_hhg.htmhttp://pediatrics.aappublications.org/cgi/content/full/115/4/1048http://us.gsk.com/products/assets/us_amoxil.pdfhttp://www.middlebrookpharma.com/releasedetail.cfm?ReleaseID=427462http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1237570http://cat.inist.fr/?aModele=afficheN&cpsidt=2654598http://cat.inist.fr/?aModele=afficheN&cpsidt=2654598http://www.medhelp.org/posts/Allergy/Rash-from-Amoxicillin/show/4008http://forums.wrongdiagnosis.com/showthread.php?t=15875http://www.medscape.com/viewarticle/430534_5http://www.racgp.org.au/cmi/txcamoxc.pdfhttp://en.wikipedia.org/w/index.php?&diff=cur&oldid=321803860http://pubchem.ncbi.nlm.nih.gov/search/?smarts=O%3DC%28O%29%5BC%40%40H%5D2N3C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29%5BC%40%40H%5D%28c1ccc%28O%29cc1%29N%29%5BC%40H%5D3SC2%28C%29Chttp://pubchem.ncbi.nlm.nih.gov/search/?smarts=O%3DC%28O%29%5BC%40%40H%5D2N3C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29%5BC%40%40H%5D%28c1ccc%28O%29cc1%29N%29%5BC%40H%5D3SC2%28C%29Chttp://www.emolecules.com/cgi-bin/search?t=ex&q=O%3DC%28O%29%5BC%40%40H%5D2N3C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29%5BC%40%40H%5D%28c1ccc%28O%29cc1%29N%29%5BC%40H%5D3SC2%28C%29Chttp://www.emolecules.com/cgi-bin/search?t=ex&q=O%3DC%28O%29%5BC%40%40H%5D2N3C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29%5BC%40%40H%5D%28c1ccc%28O%29cc1%29N%29%5BC%40H%5D3SC2%28C%29Chttp://www.chemspider.com/Chemical-Structure.31006http://www.drugbank.ca/cgi-bin/show_drug.cgi?CARD=DB01060http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=33613http://www.whocc.no/atcvet/atcvet_index/?code=QG51AX01http://www.whocc.no/atc_ddd_index/?code=J01CA04http://www.nlm.nih.gov/cgi/mesh/2009/MB_cgi?term=26787-78-0&rn=1http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=Amoxicillin+anhydroushttp://www.amoxicillinsideeffects.net/http://www.med.umich.edu/1libr/pa/pa_ampirash_hhg.htmhttp://en.wikipedia.org/w/index.php?title=British_National_Formularyhttp://pediatrics.aappublications.org/cgi/content/full/115/4/1048http://us.gsk.com/products/assets/us_amoxil.pdfhttp://en.wikipedia.org/w/index.php?title=GlaxoSmithKlinehttp://www.middlebrookpharma.com/releasedetail.cfm?ReleaseID=427462


5/5

Article Sources and Contributors 5

Article Sources and ContributorsAmoxicillin Source: http://en.wikipedia.org/w/index.php?oldid=382655420 Contributors: 213.253.39.xxx, Abhishek727, Adambro, Alchaemist, Algebraist, Allstarecho, AllyUnion, Amcfreely,

Anakenabcn, Anastrophe, Anclation, Anonymous Dissident, Anypodetos, AtonX, Avono, Beetstra, Bemoeial, Benjah-bmm27, Bmramon, Bobbhy01, Boing! said Zebedee, BrickBreyer,

BrokenSegue, Bryan Derksen, Bwhack, Can't sleep, clown will eat me, Carl.bunderson, Carlo Banez, Casforty, Cburnett, Chepry, Chowbok, Cjcollier, Constants, Conversion script,

CrazyChemGuy, Crazynas, DTOx, Dailone, Daisystanton, Daniel,levine, Danny, Davidruben, Desperado28, Divide, Dreamyshade, Drphilharmonic, DuLithgow, Dubaduba, Dyslexic3,

Dysmorodrepanis, Earthlyreason, Echuck215, Eckhart Wrner, Edruc Limited, Eleassar, Excirial, Facts707, Falcon8765, Fenghan06, Flamma, Fvasconcellos, Gaius Cornelius, GamblinMonkey,

Gil Gamesh, Gimboid, GorgeCustersSabre, Gothick, GraemeLeggett, Gregfitzy, Guanaco, Gubernator, Gurch, Guy Harris, Haham hanuka, Hanser, Havaska, Hazard-SJ, HazyM, Hehkuviini, Ian

Goddard, Insanity Incarnate, Iridescent, J.delanoy, J3ff, JForget, Javsav, Jfdwolff, Jhaochen, Kami Shkval, Khoikhoi, Kvn8907, Lenilucho, Leszek Jaczuk, Liberty Miller, Ligand13, LilHelpa,Literaturegeek, Maddiekate, Maderibeyza, Maximus Rex, Mazin07, Mboverload, Melsit, MightyWarrior, Mimarx, MithrandirAgain, Mjp797, Morr, Muchie11791, Mygerardromance, Mykhal,

Nk, Nunh-huh, Ohnoitsjamie, Omicronpersei8, P-kun80, Pcworld08g, Pharaoh of the Wizards, Philosophistry, Piano non troppo, Powertool4, Priestley1628, R. S. Shaw, Radagast83, Ralmin,

RavenFeat, Ravenous, Rbaselt, Rd232, Revjmyoung, Rgamble, Rholton, Rifleman 82, Rjwilmsi, Robert in sacramento, RoseParks, Rotring, SD6-Agent, SLi, Shawthorn, Siddhant, Silvermask,

SiobhanHansa, Skarebo, Skittleys, Skoch3, Smile a While, Snowolf, SpK, Sumeetvingkar, Tarawneh, Techelf, Terrace4, TexasPharma, Thricecube, Thumperward, Tim bates, Tmd63, Tslocum,

Tybalt01, Ukexpat, Vary, Vina, VoxLuna, WDM27, WhatamIdoing, Wright93, Xezbeth, Xiphosurus, Yodan, Zamondothegreat, , 251 anonymous edits

Image Sources, Licenses and Contributorsfile:Amoxicillin.svg Source: http://en.wikipedia.org/w/index.php?title=File:Amoxicillin.svg License: Public Domain Contributors: Ayacop, Fvasconcellos

file:Amoxicillin-3D-balls.png Source: http://en.wikipedia.org/w/index.php?title=File:Amoxicillin-3D-balls.png License: Public Domain Contributors: Benjah-bmm27, Ephemeronium

File:Yes check.svg Source: http://en.wikipedia.org/w/index.php?title=File:Yes_check.svg License: Public Domain Contributors: User:Gmaxwell, User:WarX

Image:Amoxicillin.JPG Source: http://en.wikipedia.org/w/index.php?title=File:Amoxicillin.JPG License: Creative Commons Attribution 3.0 Contributors: User:Smile a While

Image:Amoxicillin rash 3 hours after 17th dose.JPG Source: http://en.wikipedia.org/w/index.php?title=File:Amoxicillin_rash_3_hours_after_17th_dose.JPGLicense: GNU Free

Documentation License Contributors: User:Skoch3

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