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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