Cloxacillin

Cloxacillin
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
    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

    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

    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

    References

    1. 1 2 3 4 5 6 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. 1 2 3 4 "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.


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