Cloxacillin

Cloxacillin
Names
Trade namesCloxapen, others
IUPAC name
  • (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
Clinical data
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • US: B (No risk in non-human studies)
    Routes of
    use
    By mouth, IM
    Defined daily dose2 gm[1]
    External links
    AHFS/Drugs.comMicromedex Detailed Consumer Information
    Pharmacokinetics
    Bioavailability37 to 90%
    Protein binding95%
    Elimination half-life30 minutes to 1 hour
    ExcretionKidney and biliary
    Chemical and physical data
    FormulaC19H18ClN3O5S
    Molar mass435.88 g·mol−1
    3D model (JSmol)
    SMILES
    • O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1ccccc1Cl)C)[C@H]4SC3(C)C
    InChI
    • 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

    Cloxacillin is an antibiotic useful for the treatment of a number of bacterial infections.[2] This includes impetigo, cellulitis, pneumonia, septic arthritis, and otitis externa.[2] It is not effective for methicillin-resistant Staphylococcus aureus (MRSA).[3] It is used by mouth and by injection.[2]

    Side effects include nausea, diarrhea, and allergic reactions including anaphylaxis.[2] Clostridium difficile diarrhea may also occur.[3] It is not recommended in people who have previously had a penicillin allergy.[2] Use during pregnancy appears to be relatively safe.[2] Cloxacillin is in the penicillin family of medications.[3]

    Cloxacillin was patented in 1960 and approved for medical use in 1965.[4] It is on the World Health Organization's List of Essential Medicines.[5] The wholesale cost in the developing world is about US$0.16 per day for the pills.[6] It is not commercially available in the United States.[3]

    Medical uses

    Cloxacillin is in the 'access' group of the WHO AWaRe Classification.[7]

    Dosage

    The defined daily dose is 2 gm by mouth and by injection.[1] In adults the typical dose is 1 gram three times per day by mouth while in children over the age of 10 the dose is 15 mg/kg three times per day.[8] Treatment duration for impetigo is 7 days.[8]

    The injectable form is typically given as 2 gm every 6 hours in adults, though 3 grams every 6 hours may be used for certain cases.[9] In children over a month the dose is 25 to 50 mg/kg by injection every six hours.[9] When the injectable form is no longer required, switching to oral cloxacillin is not recommended. People should instead be switched from the injectable treatment to either oral cephalexin or amoxicillin/clavulanic acid as soon as possible, to complete the treatment course.[9]

    For erysipelas and cellulitis, the doses of cloxacillin is usually half that for severe infections.[9]

    Cloxacillin dosage for severe infections
    Age categoryWeight (kg)By mouthBy injection over 60 min (500 mg vial, diluted in 4 ml, 125 mg/ml)
    1 to 3 mths4 to 6 1 ml 4 times/day[9]
    3 to 12 mths6 to 10 2 ml 4 times/day[9]
    1 to 5 yrs10 to 20 4 ml 4 times/day[9]
    5 to 8 yrs20 to 28 8 ml 4 times/day[9]
    8 to 12 yrs28 to 38 12 ml 4 times/day[8]
    12 to 13 yrs38 to 45 500 mg 3 times/day[8]16 ml 4 times/day[9]
    13 to 15 yrs45 to 55 750 mg 3 times/day[8]16 ml 4 times/day[9]
    Adult≥ 55 1 gm three 3 times/day[8]2 gm 4 times/day[9]

    Mechanism of action

    It is semisynthetic and in the same class as penicillin.[10] Cloxacillin is used against staphylococci that produce beta-lactamase. Cloxacillin's side chain acts as a barrier to the bacteria's enzyme and it works by breaking down the bacterial cell wall. Its absorption is reduced by food.[11] Staph. aureus has shown resistance to cloxacillin, hence requiring alternative antibiotics.[11]

    Society and culture

    Beecham (now GlaxoSmithKline) discovered and developed cloxacillin by making modifications to methicillin in the early 1960s.[10]

    Cloxacillin is sold under a number of trade names, including Cloxapen,[12] Cloxacap,[13] Tegopen,[14] and commonly for veterinary use, Orbenin.[15] It is not commercially available in the United States.[3] It is available in Canada.[11]

    See also

    References

    1. 1 2 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 21 January 2021. Retrieved 30 August 2020.
    2. 1 2 3 4 5 6 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.
    3. 1 2 3 4 5 "Cloxacillin (Professional Patient Advice)". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
    4. 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.
    5. 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.
    6. "Cloxacillin Sodium". International Drug Price Indicator Guide. Archived from the original on 25 August 2018. Retrieved 8 December 2016.
    7. Zanichelli, Veronica; Sharland, Michael; Cappello, Bernadette; Moja, Lorenzo; Getahun, Haileyesus; Pessoa-Silva, Carmem; Sati, Hatim; van Weezenbeek, Catharina; Balkhy, Hanan; Simão, Mariângela; Gandra, Sumanth; Huttner, Benedikt (1 April 2023). "The WHO AWaRe (Access, Watch, Reserve) antibiotic book and prevention of antimicrobial resistance". Bulletin of the World Health Organization. 101 (4): 290–296. doi:10.2471/BLT.22.288614. ISSN 0042-9686. Archived from the original on 7 May 2023. Retrieved 17 November 2023.
    8. 1 2 3 4 5 6 "Cloxacillin oral - Essential drugs". medicalguidelines.msf.org. Archived from the original on 29 August 2021. Retrieved 30 August 2020.
    9. 1 2 3 4 5 6 7 8 9 10 11 "Cloxacillin injectable - Essential drugs". medicalguidelines.msf.org. Archived from the original on 29 August 2021. Retrieved 1 September 2020.
    10. 1 2 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.
    11. 1 2 3 Sealock, Kara; Seneviratne, Cydnee; Lilley, Linda Lane; Collins, Shelly Rainforth; Snyder, Julie S. (2021). "43. Antibiotics Part 1. Sulfonamides, penicillins, cephalosporins, macrocodes and tetracyclines". Lilley's Pharmacology for Canadian Health Care Practice - E-Book (4th ed.). Elsevier. pp. 700–701. ISBN 978-0-323-69480-3. Archived from the original on 2021-08-29. Retrieved 2020-12-30.
    12. "Cloxapen". pubchem.ncbi.nlm.nih.gov. Archived from the original on 29 August 2021. Retrieved 30 December 2020.
    13. "Cloxacap Full Prescribing Information, Dosage & Side Effects | MIMS Singapore". www.mims.com. Archived from the original on 2021-08-29. Retrieved 2020-12-30.
    14. "Tegopen Drug Interactions". Drugs.com. Archived from the original on 12 August 2020. Retrieved 30 December 2020.
    15. "Orbenin". Drugs.com. Archived from the original on 12 August 2020. Retrieved 30 December 2020.
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