Cloxacillin

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Cloxacillin
Cloxacillin.svg
Cloxacillin-based-on-xtal-3D-bs-17.png
Clinical data
Trade names Cloxapen, others
AHFS/Drugs.com Micromedex Detailed Consumer Information
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
  • (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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.468 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H18ClN3O5S
Molar mass 435.88 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 Yes check.svgY
  • Key:LQOLIRLGBULYKD-JKIFEVAISA-N Yes check.svgY
   (verify)

Cloxacillin is an antibiotic useful for the treatment of several 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 can be used by mouth and by injection. [1]

Contents

Side effects include nausea, diarrhea, and allergic reactions including anaphylaxis. [1] Clostridioides 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. [4] 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.[ citation needed ]

Society and culture

Cloxacillin was discovered and developed by Beecham (now GlaxoSmithKline). [5]

It is sold under a number of trade names, including Cloxapen, Cloxacap, Tegopen and Orbenin. [6]

See also

References

  1. 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.
  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 J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN   9783527607495. Archived from the original on 2016-12-20.
  4. ↑ 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.
  5. ↑ Greenwood D (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.
  6. ↑ Gollakner R (2023-05-09). "Cloxacillin". VCA Animal Hospitals. Retrieved 2023-05-09.
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