Cloxacillin

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 names	Cloxapen
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	US: B (No risk in non-human studies)
Routes of administration	Oral, IM
Pharmacokinetic data
Bioavailability	37 to 90%
Protein binding	95%
Biological half-life	30 minutes to 1 hour
Excretion	Renal and biliary
Identifiers
CAS Number	61-72-3 Y
ATC code	J01CF02 (WHO) QJ51CF02 (WHO) QS01AA90 (WHO)
PubChem	CID: 6098
DrugBank	DB01147 Y
ChemSpider	5873 Y
UNII	O6X5QGC2VB Y
KEGG	D07733 Y
ChEBI	CHEBI:49566 Y
ChEMBL	CHEMBL891 Y
Chemical data
Formula	C19H18ClN3O5S
Molecular mass	435.88 g/mol
SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1ccccc1Cl)C)[C@H]4SC3(C)C
InChI InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1 Y Key:LQOLIRLGBULYKD-JKIFEVAISA-N Y
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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. 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, the most important medication needed in a basic health system.

See also

• Dicloxacillin
• Flucloxacillin
• Nafcillin
• Oxacillin