Cloxacillin

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Cloxacillin
Cloxacillin.svg
Cloxacillin ball-and-stick.png
Systematic (IUPAC) name
(2S,5R,6R)-6-{[3-(2-chlorophenyl)-5-methyl-
oxazole-4-carbonyl]amino}-3,3-dimethyl-7-oxo-
4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
Trade namesCloxapen
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy cat.B (US)
Legal status?
RoutesOral, IM
Pharmacokinetic data
Bioavailability37 to 90%
Protein binding95%
Half-life30 minutes to 1 hour
ExcretionRenal and biliary
Identifiers
CAS number61-72-3 YesY
ATC codeJ01CF02 QJ51CF02 QS01AA90
PubChemCID 6098
DrugBankDB01147
ChemSpider5873 YesY
UNIIO6X5QGC2VB YesY
KEGGD07733 YesY
ChEBICHEBI:49566 YesY
ChEMBLCHEMBL891 YesY
Chemical data
FormulaC19H18ClN3O5S 
Mol. mass435.88 g/mol
 YesY (what is this?)  (verify)
 
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Cloxacillin
Cloxacillin.svg
Cloxacillin ball-and-stick.png
Systematic (IUPAC) name
(2S,5R,6R)-6-{[3-(2-chlorophenyl)-5-methyl-
oxazole-4-carbonyl]amino}-3,3-dimethyl-7-oxo-
4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
Trade namesCloxapen
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy cat.B (US)
Legal status?
RoutesOral, IM
Pharmacokinetic data
Bioavailability37 to 90%
Protein binding95%
Half-life30 minutes to 1 hour
ExcretionRenal and biliary
Identifiers
CAS number61-72-3 YesY
ATC codeJ01CF02 QJ51CF02 QS01AA90
PubChemCID 6098
DrugBankDB01147
ChemSpider5873 YesY
UNIIO6X5QGC2VB YesY
KEGGD07733 YesY
ChEBICHEBI:49566 YesY
ChEMBLCHEMBL891 YesY
Chemical data
FormulaC19H18ClN3O5S 
Mol. mass435.88 g/mol
 YesY (what is this?)  (verify)

Cloxacillin is an antibiotic useful for the treatment of a number of bacterial infections. It is semisynthetic and in the same class as penicillin.

Cloxacillin is used against staphylococci that produce beta-lactamase, due to its large R chain, which does not allow the beta-lactamases to bind. This drug has a weaker antibacterial activity than benzylpenicillin, and is devoid of serious toxicity except for allergic reactions.

Cloxacillin was discovered and developed by Beecham.[1] It is sold under a number of trade names, including Cloxapen, Cloxacap, Tegopen and Orbenin. It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[2]

See also[edit]

References[edit]

  1. ^ David Greenwood (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–. ISBN 978-0-19-953484-5. Retrieved 18 November 2010. 
  2. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014.