Cloxacillin

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Cloxacillin
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
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 a semisynthetic antibiotic in the same class as penicillin. Cloxacillin was discovered and developed by Beecham.[1] It is sold under a number of trade names, including Cloxapen, Cloxacap, Tegopen and Orbenin.

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.

It has been suggested, in one study, that increased use of cloxacillin may permit reduced use of vancomycin.[2]

See also[edit]

References[edit]