Beta-lactam antibiotic
Cloxacillin Trade names Cloxapen, others AHFS /Drugs.com Micromedex Detailed Consumer Information Routes of administration By mouth , IM ATC code Bioavailability 37 to 90% Protein binding 95% Elimination half-life 30 minutes to 1 hour Excretion kidney and biliary
(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 PubChem CID DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.000.468 Formula C 19 H 18 Cl N 3 O 5 S Molar mass 435.88 g·mol−1 3D model (JSmol )
O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1ccccc1Cl)C)[C@H]4SC3(C)C
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
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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]
Mechanism of action
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 ]
Society and culture
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]
See also
References
External links
"Cloxacillin" . Drug Information Portal . U.S. National Library of Medicine.