Cloxacillin

Cloxacillin
Clinical data
Trade names	Cloxapen, others
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of; administration	By mouth, 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	kidney 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 or 5 methyl 3(2 chlorophenyl)4 isoxazoyl penicillin;
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−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 several bacterial infections. This includes impetigo, cellulitis, pneumonia, septic arthritis, and otitis externa. It is not effective for methicillin-resistant Staphylococcus aureus (MRSA). It can be used by mouth and by injection.

Side effects include nausea, diarrhea, and allergic reactions including anaphylaxis. Clostridioides difficile diarrhea may also occur. It is not recommended in people who have previously had a penicillin allergy. Use during pregnancy appears to be relatively safe. Cloxacillin is in the penicillin family of medications.

Cloxacillin was patented in 1960 and approved for medical use in 1965. It is on the World Health Organization's List of Essential Medicines. It is not commercially available in the United States.