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Revision as of 12:17, 4 March 2015 editJytdog (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers187,951 editsm Undid revision 649809466 by 80.42.29.75 (talk) revert edits by sock of blocked editor Nuklear← Previous edit Revision as of 14:13, 27 June 2015 edit undoDePiep (talk | contribs)Extended confirmed users294,285 editsm Infobox drug: rm/replace deprecated params. Fix unk parameters (via AWB script)Next edit →
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| image = Cloxacillin.svg | image = Cloxacillin.svg
| image2 = Cloxacillin ball-and-stick.png | image2 = Cloxacillin ball-and-stick.png

<!--Clinical data--> <!--Clinical data-->
| tradename = Cloxapen | tradename = Cloxapen
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| legal_status = | legal_status =
| routes_of_administration = Oral, ] | routes_of_administration = Oral, ]

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 37 to 90% | bioavailability = 37 to 90%
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| elimination_half-life = 30 minutes to 1 hour | elimination_half-life = 30 minutes to 1 hour
| excretion = ] and biliary | excretion = ] and biliary

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 61-72-3 | CAS_number = 61-72-3
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| PubChem = 6098 | PubChem = 6098
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01147 | DrugBank = DB01147
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5873 | ChemSpiderID = 5873
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| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 891 | ChEMBL = 891

<!--Chemical data--> <!--Chemical data-->
| C=19 | H=18 | Cl=1 | N=3 | O=5 | S=1 | C=19 | H=18 | Cl=1 | N=3 | O=5 | S=1
| molecular_weight = 435.88 g/mol | molecular_weight = 435.88 g/mol
| smiles = O=C(O)3N4C(=O)(NC(=O)c2c(onc2c1ccccc1Cl)C)4SC3(C)C | smiles = O=C(O)3N4C(=O)(NC(=O)c2c(onc2c1ccccc1Cl)C)4SC3(C)C

Revision as of 14:13, 27 June 2015

Pharmaceutical compound
Cloxacillin
Clinical data
Trade namesCloxapen
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Oral, IM
ATC code
Pharmacokinetic data
Bioavailability37 to 90%
Protein binding95%
Elimination half-life30 minutes to 1 hour
ExcretionRenal and biliary
Identifiers
IUPAC name
  • (2S,5R,6R)-6-{amino}-3,3-dimethyl-7-oxo-
    4-thia-1-azabicycloheptane-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.468 Edit this at Wikidata
Chemical and physical data
FormulaC19H18ClN3O5S
Molar mass435.88 g/mol g·mol
3D model (JSmol)
SMILES
  • O=C(O)3N4C(=O)(NC(=O)c2c(onc2c1ccccc1Cl)C)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
  • Key:LQOLIRLGBULYKD-JKIFEVAISA-N
  (verify)

Cloxacillin is an antibiotic useful for the treatment of a number of bacterial infections. 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.

Cloxacillin was discovered and developed by Beecham. It is sold under a number of trade names, including Cloxapen, Cloxacap, Tegopen and Orbenin. It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.

See also

References

  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. Retrieved 18 November 2010.
  2. "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
Antibacterials active on the cell wall and envelope (J01C-J01D)
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking: Ramoplanin
Intracellular
Other
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