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| Clinical data | |
|---|---|
| Trade names | Cloxapen, others |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| Routes of administration | By mouth, IM |
| ATC code | |
| Pharmacokinetic data | |
| Bioavailability | 37 to 90% |
| Protein binding | 95% |
| Elimination half-life | 30 minutes to 1 hour |
| Excretion | kidney and biliary |
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| PubChem CID | |
| DrugBank |
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| ChemSpider |
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| UNII | |
| KEGG |
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| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.000.468  |
| Chemical and physical data | |
| Formula | C19H18ClN3O5S |
| Molar mass | 435.88 g·mol−1 |
| 3D model (JSmol) | |
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Cloxacillin is an antibiotic useful for the treatment of a number of 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] Clostridium 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]
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