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 Y
PubChem CID	6098
DrugBank	DB01147 Y
ChemSpider	5873 Y
UNII	O6X5QGC2VB
KEGG	D07733 Y
ChEBI	CHEBI:49566 Y
ChEMBL	ChEMBL891 Y
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 Y Key:LQOLIRLGBULYKD-JKIFEVAISA-N Y
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Cloxacillin is an antibiotic useful for the treatment of several bacterial infections.^[1] This includes impetigo, cellulitis, pneumonia, septic arthritis, and otitis externa.^[1] It is not effective for methicillin-resistant Staphylococcus aureus (MRSA).^[2] It can be used by mouth and by injection.^[1]

Side effects include nausea, diarrhea, and allergic reactions including anaphylaxis.^[1] Clostridioides difficile diarrhea may also occur.^[2] It is not recommended in people who have previously had a penicillin allergy.^[1] Use during pregnancy appears to be relatively safe.^[1] Cloxacillin is in the penicillin family of medications.^[2]

Cloxacillin was patented in 1960 and approved for medical use in 1965.^[3] It is on the World Health Organization's List of Essential Medicines.^[4] It is not commercially available in the United States.^[2]

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.^{[citation needed]}

Cloxacillin was discovered and developed by Beecham (now GlaxoSmithKline).^[5]

It is sold under a number of trade names, including Cloxapen, Cloxacap, Tegopen and Orbenin.^[6]

• Dicloxacillin
• Flucloxacillin
• Nafcillin
• Oxacillin

• "Cloxacillin". Drug Information Portal. U.S. National Library of Medicine.

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