Cloxacillin

Cloxacillin
Clinical data
Trade namesCloxapen, others
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		By mouth, IM
ATC code
Pharmacokinetic data
Bioavailability37 to 90%
Protein binding95%
Elimination half-life30 minutes to 1 hour
Excretionkidney and biliary
Identifiers
  • (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 InfoCard100.000.468 Edit this at Wikidata
Chemical and physical data
FormulaC19H18ClN3O5S
Molar mass435.88 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 checkY
  • Key:LQOLIRLGBULYKD-JKIFEVAISA-N checkY
  (verify)

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]

  1. ^ a b c d e f World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 98, 100, 110–111, 586, 602, 614, 623. hdl:10665/44053. ISBN 9789241547659.
  2. ^ a b c d "Cloxacillin (Professional Patient Advice)". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
  3. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495. Archived from the original on 2016-12-20.
  4. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.