Cloxacillin

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Cloxacillin
Names
Trade namesCloxapen, others
  • (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 AWaRe
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)
  • 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

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 category Weight (kg) By mouth By injection over 60 min (500 mg vial, diluted in 4 ml, 125 mg/ml)
1 to 3 mths 4 to 6 1 ml 4 times/day[9]
3 to 12 mths 6 to 10 2 ml 4 times/day[9]
1 to 5 yrs 10 to 20 4 ml 4 times/day[9]
5 to 8 yrs 20 to 28 8 ml 4 times/day[9]
8 to 12 yrs 28 to 38 12 ml 4 times/day[8]
12 to 13 yrs 38 to 45 500 mg 3 times/day[8] 16 ml 4 times/day[9]
13 to 15 yrs 45 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. ↑ 1.0 1.1 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 21 January 2021. Retrieved 30 August 2020.
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 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. ↑ 3.0 3.1 3.2 3.3 3.4 "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. ↑ 8.0 8.1 8.2 8.3 8.4 8.5 "Cloxacillin oral - Essential drugs". medicalguidelines.msf.org. Archived from the original on 29 August 2021. Retrieved 30 August 2020.
  9. ↑ 9.00 9.01 9.02 9.03 9.04 9.05 9.06 9.07 9.08 9.09 9.10 "Cloxacillin injectable - Essential drugs". medicalguidelines.msf.org. Archived from the original on 29 August 2021. Retrieved 1 September 2020.
  10. ↑ 10.0 10.1 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. ↑ 11.0 11.1 11.2 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.

External links

External sites:
Identifiers:
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