Cloxacillin

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Cloxacillin
Cloxacillin.svg
Cloxacillin ball-and-stick.png
Clinical data
Trade names Cloxapen, others
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy
category
  • US: B (No risk in non-human studies)
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
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.000.468 Edit this at Wikidata
Chemical and physical data
Formula C19H18ClN3O5S
Molar mass 435.88 g/mol
3D model (JSmol)
  (verify)

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 is 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, the most effective and safe medicines needed in a health system.[4] The wholesale cost in the developing world is about 0.16 USD per day for the pills.[5] It is not commercially available in the United States.[2]

Mechanism of action[edit]

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.

Society and culture[edit]

Cloxacillin was discovered and developed by Beecham.[6]

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

See also[edit]

References[edit]

  1. ^ a b c d e f WHO Model Formulary 2008 (PDF). World Health Organization. 2009. pp. 110, 586. ISBN 9789241547659. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
  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, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495. Archived from the original on 2016-12-20.
  4. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
  5. ^ "Cloxacillin Sodium". International Drug Price Indicator Guide. Retrieved 8 December 2016.
  6. ^ David Greenwood (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–. ISBN 978-0-19-953484-5. Archived from the original on 6 June 2013. Retrieved 18 November 2010.