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Ampicillin 1

Ampicillin

Ampicillin

Systematic (IUPAC) name

(2S,5R,6R)-6-([(2R)-2-amino-2-phenylacetyl]amino)

-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-

carboxylic acid

Identifiers

CAS number 69-53-4[1]

ATC code J01 CA01[2]

S01 AA19[3]

QJ51 CA01[4]

PubChem CID 6249[5]

DrugBankDB00415

[6]

ChemSpider 6013[7]

Chemical data

Formula C16

H19

N3O

4S

Mol. mass 349.41 gmol1

SMILES eMolecules[8]

& PubChem[9]

Pharmacokinetic data

Bioavailability 40% (oral)

Protein binding 15 to 25%

Metabolism 12 to 50%

Half-life approx 1 hour

Excretion 75 to 85% renal

Therapeutic considerations

Pregnancy cat. A (Au), B (U.S.)

Legal status

Routes Oral, intravenous

(what is this?) (verify)[10]

http://en.wikipedia.org/w/index.php?&diff=cur&oldid=321808428http://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.wikipedia.org/w/index.php?title=Route_of_administrationhttp://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=Drug_metabolismhttp://en.wikipedia.org/w/index.php?title=Plasma_protein_bindinghttp://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%28c1ccccc1%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%28c1ccccc1%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=Molhttp://en.wikipedia.org/w/index.php?title=Grammhttp://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.6013http://en.wikipedia.org/w/index.php?title=ChemSpiderhttp://www.drugbank.ca/cgi-bin/show_drug.cgi?CARD=DB00415http://en.wikipedia.org/w/index.php?title=DrugBankhttp://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6249http://en.wikipedia.org/w/index.php?title=PubChemhttp://www.whocc.no/atcvet/atcvet_index/?code=QJ51CA01http://en.wikipedia.org/w/index.php?title=ATCvet_code_QJ51http://www.whocc.no/atc_ddd_index/?code=S01AA19http://en.wikipedia.org/w/index.php?title=ATC_code_S01http://www.whocc.no/atc_ddd_index/?code=J01CA01http://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=69-53-4&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:Ampicillin_3d_structure.pnghttp://en.wikipedia.org/w/index.php?title=File:Ampicillin_Structural_Formulae_V.1.svg

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Ampicillin 2

Ampicillin is a beta-lactam antibiotic that has been used extensively to treat bacterial infections since 1961. Until the

introduction of ampicillin by the British company Beecham, penicillin therapies had only been effective against

Gram-positive organisms such as staphylococci and streptococci. Ampicillin (originally branded as 'Penbritin') also

demonstrated activity against Gram-negative organisms such asH. influenzae, coliforms andProteus spp. Ampicillin

was the first of a number of so-called broad spectrum penicillins subsequently introduced by Beecham. Ampicillin is

part of the aminopenicillin family and is roughly equivalent to its successor, amoxicillin in terms of spectrum and

level of activity[11]

. It can sometimes result in reactions that range in severity from a rash (in the case of patients that

may unwittingly have mononucleosis) to potentially lethal allergic reactions such as anaphylaxis. However, as with

other penicillin drugs, it is relatively non-toxic and adverse effects of a serious nature are encountered only

infrequently.

Mechanism of action

Belonging to the penicillin group of beta-lactam antibiotics, ampicillin is able to penetrate Gram-positive and some

Gram-negative bacteria. It differs from penicillin only by the presence of an amino group. That amino group helps

the drug penetrate the outer membrane of gram-negative bacteria.

Ampicillin acts as a competitive inhibitor of the enzyme transpeptidase, which is needed by bacteria to make their

cell walls.[11]

It inhibits the third and final stage of bacterial cell wall synthesis in binary fission, which ultimately

leads to cell lysis. The holes that appear in the cell walls allow the bodys immune system to take over and fight off

the bacteria. Ampicillin has received FDA approval for its action of mechanism.

Effects on chloroplast division

Ampicillin, like other -lactam antibiotics, not only blocks the division of bacteria, but also the division of

chloroplasts of the Glaucophytes (called cyanelles) and chloroplasts of the mossPhyscomitrella patens, a bryophyte.

In contrast, it has no effect on the plastids of the higher developed vascular plant Lycopersicon esculentum L.

(tomato)[12]

.

Application

Ampicillin is closely related to amoxicillin, another type of penicillin, and both are used to treat urinary tract

infections, otitis media, uncomplicated community-acquired pneumonia,Haemophilus influenzae, salmonellosis and

Listeria meningitis. It is used with flucloxacillin in the combination antibiotic co-fluampicil for empiric treatment of

cellulitis; providing cover against Group A streptococcal infection whilst the flucloxacillin acts against the

Staphylococcus aureus bacterium. Of concern is the number of bacteria that become resistant to Ampicillin

necessitating combination therapy or use of other antibiotics.

AllPseudomonas and most strains ofKlebsiella andAerobacterare considered resistant.[13]

Use in research

Ampicillin is often used as a selective agent in molecular biology to select for and to confirm the uptake of genes

(e.g., of plasmids) by bacteria (e.g.,E. coli). A gene that is to be inserted into a bacterium is coupled to a gene coding

for an ampicillin resistance (inE. coli, usually the bla (TEM-1) gene, coding for -lactamase). The treated bacteria

are then grown in a medium containing ampicillin (typically 50100 mg/L). Only the bacteria that successfully take

up the desired genes become ampicillin resistant, and therefore contain the other desired gene as well. It can be used

with Cloaxicillin as well. As a powder ampicillin is white with slight yellow cast and is soluble in water

(150 mg/ml).

http://en.wikipedia.org/w/index.php?title=Beta-lactamasehttp://en.wikipedia.org/w/index.php?title=E._colihttp://en.wikipedia.org/w/index.php?title=Plasmidhttp://en.wikipedia.org/w/index.php?title=Genehttp://en.wikipedia.org/w/index.php?title=Molecular_biologyhttp://en.wikipedia.org/w/index.php?title=Aerobacterhttp://en.wikipedia.org/w/index.php?title=Klebsiellahttp://en.wikipedia.org/w/index.php?title=Pseudomonashttp://en.wikipedia.org/w/index.php?title=Antibioticshttp://en.wikipedia.org/w/index.php?title=Antibiotic_resistancehttp://en.wikipedia.org/w/index.php?title=Staphylococcus_aureushttp://en.wikipedia.org/w/index.php?title=Group_A_streptococcal_infectionhttp://en.wikipedia.org/w/index.php?title=Cellulitishttp://en.wikipedia.org/w/index.php?title=Empiricalhttp://en.wikipedia.org/w/index.php?title=Co-fluampicilhttp://en.wikipedia.org/w/index.php?title=Flucloxacillinhttp://en.wikipedia.org/w/index.php?title=Meningitishttp://en.wikipedia.org/w/index.php?title=Listeriosishttp://en.wikipedia.org/w/index.php?title=Salmonellosishttp://en.wikipedia.org/w/index.php?title=Haemophilus_influenzaehttp://en.wikipedia.org/w/index.php?title=Pneumoniahttp://en.wikipedia.org/w/index.php?title=Otitis_mediahttp://en.wikipedia.org/w/index.php?title=Urinary_tract_infectionshttp://en.wikipedia.org/w/index.php?title=Urinary_tract_infectionshttp://en.wikipedia.org/w/index.php?title=Amoxicillinhttp://en.wikipedia.org/w/index.php?title=Tomatohttp://en.wikipedia.org/w/index.php?title=Vascular_planthttp://en.wikipedia.org/w/index.php?title=Plastidhttp://en.wikipedia.org/w/index.php?title=Bryophytehttp://en.wikipedia.org/w/index.php?title=Physcomitrella_patenshttp://en.wikipedia.org/w/index.php?title=Glaucophytehttp://en.wikipedia.org/w/index.php?title=Chloroplasthttp://en.wikipedia.org/w/index.php?title=Beta-lactamhttp://en.wikipedia.org/w/index.php?title=Lysishttp://en.wikipedia.org/w/index.php?title=Binary_fissionhttp://en.wikipedia.org/w/index.php?title=Cell_wallhttp://en.wikipedia.org/w/index.php?title=DD-transpeptidasehttp://en.wikipedia.org/w/index.php?title=Aminohttp://en.wikipedia.org/w/index.php?title=Gram-negativehttp://en.wikipedia.org/w/index.php?title=Gram-positivehttp://en.wikipedia.org/w/index.php?title=Penicillinhttp://en.wikipedia.org/w/index.php?title=Anaphylaxishttp://en.wikipedia.org/w/index.php?title=Infectious_mononucleosishttp://en.wikipedia.org/w/index.php?title=Rashhttp://en.wikipedia.org/w/index.php?title=Amoxicillinhttp://en.wikipedia.org/w/index.php?title=Aminopenicillinhttp://en.wikipedia.org/w/index.php?title=Proteushttp://en.wikipedia.org/w/index.php?title=Coliformhttp://en.wikipedia.org/w/index.php?title=H._influenzaehttp://en.wikipedia.org/w/index.php?title=Gram-negativehttp://en.wikipedia.org/w/index.php?title=Streptococcushttp://en.wikipedia.org/w/index.php?title=Staphylococcushttp://en.wikipedia.org/w/index.php?title=Gram-positivehttp://en.wikipedia.org/w/index.php?title=Beecham_%28pharmaceutical_company%29http://en.wikipedia.org/w/index.php?title=Infectionhttp://en.wikipedia.org/w/index.php?title=Bacteriumhttp://en.wikipedia.org/w/index.php?title=Antibiotichttp://en.wikipedia.org/w/index.php?title=Beta-lactam_antibiotic

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Ampicillin 3

References

[1] http://www.nlm. nih.gov/cgi/mesh/2009/MB_cgi?term=69-53-4&rn=1

[2] http://www.whocc. no/atc_ddd_index/?code=J01CA01

[3] http://www.whocc. no/atc_ddd_index/?code=S01AA19

[4] http://www.whocc. no/atcvet/atcvet_index/?code=QJ51CA01

[5] http://pubchem.ncbi. nlm.nih.gov/summary/summary.cgi?cid=6249

[6] http://www.drugbank. ca/cgi-bin/show_drug.cgi?CARD=DB00415[7] http://www.chemspider. com/Chemical-Structure.6013

[8] 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%28c1ccccc1%29N%29

[9] 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%28c1ccccc1%29

[10] http://en.wikipedia.org/w/index. php?&diff=cur&oldid=321808428

[11] AHFS DRUG INFORMATION 2006(2006 ed.). American Society of Health-System Pharmacists. 2006.

[12] Britta Kasten und Ralf Reski (1997): -lactam antibiotics inhibit chloroplast division in a moss (Physcomitrella patens) but not in tomato

(Lycopersicon esculentum). Journal of Plant Physiology 150, 137-140. (http://cat.inist. fr/?aModele=afficheN&cpsidt=2640663)

[13] Mosby's Drug Consult 2006(16 ed.). Mosby, Inc.. 2006.

http://cat.inist.fr/?aModele=afficheN&cpsidt=2640663http://en.wikipedia.org/w/index.php?title=Plant_Physiologyhttp://en.wikipedia.org/w/index.php?title=Beta-lactamhttp://en.wikipedia.org/w/index.php?title=Ralf_Reskihttp://en.wikipedia.org/w/index.php?&diff=cur&oldid=321808428http://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%28c1ccccc1%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%28c1ccccc1%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%28c1ccccc1%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%28c1ccccc1%29N%29%5BC%40H%5D3SC2%28C%29Chttp://www.chemspider.com/Chemical-Structure.6013http://www.drugbank.ca/cgi-bin/show_drug.cgi?CARD=DB00415http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6249http://www.whocc.no/atcvet/atcvet_index/?code=QJ51CA01http://www.whocc.no/atc_ddd_index/?code=S01AA19http://www.whocc.no/atc_ddd_index/?code=J01CA01http://www.nlm.nih.gov/cgi/mesh/2009/MB_cgi?term=69-53-4&rn=1

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Article Sources and Contributors 4

Article Sources and ContributorsAmpicillin Source: http://en.wikipedia.org/w/index.php?oldid=379888677 Contributors: Alasdair, Alnokta, Anypodetos, Arcadian, AxelBoldt, Badgernet, Beetstra, Benjah-bmm27, Bernfarr,

Casforty, Chowbok, ClockworkSoul, ClockworkTroll, Conversion script, Courcelles, Davidruben, Ddorn 1999, Eakka, ElAmericano, Epbr123, Fvasconcellos, Fythrion, Giorgiogp2, Gogo Dodo,

Grafen, Gutsul, Harbinary, Heegoop, Hehkuviini, Heron, Jfdwolff, J, Kappa, Katalaveno, Kpjas, Linefeed, LittleT889, Lucas Duke, Lucubrator Lem, M1ss1ontomars2k4, M3a1xx, Magnus

Manske, MarcoTolo, Mcorazao, Michael Hardy, Mysid, Nikkimaria, Nirmos, Noisy, Nunh-huh, Outriggr, Pcworld08g, Phuzion, Pmaclean, RJHall, Rifleman 82, Rocaveli, Sabedon, Sabisteb,

Sedmic, Selket, Shaggyjacobs, Sirmelle, Slucas, Snow64, Techelf, Thricecube, Vedran12, Welsh, Wickey-nl, , 85 anonymous edits

Image Sources, Licenses and Contributorsfile:Ampicillin Structural Formulae V.1.svg Source: http://en.wikipedia.org/w/index.php?title=File:Ampicillin_Structural_Formulae_V.1.svgLicense: Public Domain Contributors: User:J

file:Ampicillin_3d_structure.png Source: http://en.wikipedia.org/w/index.php?title=File:Ampicillin_3d_structure.pngLicense: Creative Commons Attribution-Sharealike 3.0 Contributors:

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