Cloxacillin

Cloxacillin
Clinical data
Trade names	Cloxapen
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of; administration	Oral, IM
ATC code	J01CF02 (WHO) QJ51CF02 (WHO) QS01AA90 (WHO);
Pharmacokinetic data
Bioavailability	37 to 90%
Protein binding	95%
Elimination half-life	30 minutes to 1 hour
Excretion	Renal and biliary
Identifiers
	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;
CAS Number	61-72-3 ;
PubChem CID	6098;
DrugBank	DB01147 ;
ChemSpider	5873 ;
UNII	O6X5QGC2VB;
KEGG	D07733 ;
ChEBI	CHEBI:49566 ;
ChEMBL	ChEMBL891 ;
CompTox Dashboard (EPA)	DTXSID5022853 ;
ECHA InfoCard	100.000.468
Chemical and physical data
Formula	C19H18ClN3O5S
Molar mass	435.88 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:LQOLIRLGBULYKD-JKIFEVAISA-N ;
	(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, the most important medication needed in a basic health system.^[2]

References

^ 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.
^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

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[Greenwood2008-1] 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" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

[1]

[2]

See also

References