Cloxacillin






































































































Cloxacillin
Cloxacillin.svg
Cloxacillin ball-and-stick.png
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

  • J01CF02 (WHO) QJ51CF02 (WHO) QS01AA90 (WHO)

Pharmacokinetic data
Bioavailability 37 to 90%
Protein binding 95%
Elimination half-life
 30 minutes to 1 hour
Excretion
kidney and biliary
Identifiers
CAS Number

  • 61-72-3 ☑Y

PubChem CID
  • 6098
DrugBank

  • DB01147 ☑Y
ChemSpider

  • 5873 ☑Y
UNII
  • O6X5QGC2VB
KEGG

  • D07733 ☑Y
ChEBI

  • CHEBI:49566 ☑Y
ChEMBL

  • ChEMBL891 ☑Y
ECHA InfoCard
100.000.468 Edit this at Wikidata
Chemical and physical data
Formula
C19H18ClN3O5S
Molar mass 435.88 g/mol
3D model (JSmol)
  • Interactive image

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  (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 US$0.16 per day for the pills.[5] It is not commercially available in the United States.[2]




Contents






  • 1 Mechanism of action


  • 2 Society and culture


  • 3 See also


  • 4 References





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



  • Dicloxacillin

  • Flucloxacillin

  • Nafcillin

  • Oxacillin



References





  1. ^ abcdef 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..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}


  2. ^ abcd "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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