Cloxacillin

Cloxacillin
Cloxacillin
Systematic (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
Clinical data
Trade names Cloxapen
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy cat. B(US)
Legal status  ?
Routes Oral, IM
Pharmacokinetic data
Bioavailability 37 to 90%
Protein binding 95%
Half-life 30 minutes to 1 hour
Excretion Renal and biliary
Identifiers
CAS number 61-72-3 YesY
ATC code J01CF02 QJ51CF02 QS01AA90
PubChem CID 6098
DrugBank APRD00882
ChemSpider 5873 YesY
UNII O6X5QGC2VB YesY
KEGG D07733 YesY
ChEBI CHEBI:49566 YesY
ChEMBL CHEMBL891 YesY
Chemical data
Formula C19H18ClN3O5S 
Mol. mass 435.88 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Cloxacillin is a semisynthetic antibiotic in the same class as penicillin. Cloxacillin was discovered and developed by Beecham.[1] It is sold under a number of trade names, including Cloxapen, Cloxacap, Tegopen and Orbenin.

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.

It has been suggested, in one study, that increased use of cloxacillin may permit reduced use of vancomycin.[2]

See also

References

  1. ^ David Greenwood (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–. ISBN 9780199534845. http://books.google.com/books?id=i4_FZHmzjzwC&pg=PA124. Retrieved 18 November 2010. 
  2. ^ Lawrence SL, Roth V, Slinger R, Toye B, Gaboury I, Lemyre B (2005). "Cloxacillin versus vancomycin for presumed late-onset sepsis in the Neonatal Intensive Care Unit and the impact upon outcome of coagulase negative staphylococcal bacteremia: a retrospective cohort study". BMC Pediatr 5: 49. doi:10.1186/1471-2431-5-49. PMC 1343548. PMID 16375769. http://www.biomedcentral.com/1471-2431/5/49. 
v · d · eAntibacterials: cell envelope antibiotics (J01C-J01D)
Intracellular
inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) • DADAL/AR inhibitors (Cycloserine) • bactoprenol inhibitors (Bacitracin)
Glycopeptide
inhibit PG chain elongation: Vancomycin# (Oritavancin, Telavancin) • Teicoplanin (Dalbavancin) • Ramoplanin
β-lactams/
(inhibit PBP
cross-links)
Penicillins/
(penams)

Benzylpenicillin (G)#: Clometocillin • Benzathine benzylpenicillin#  • Procaine benzylpenicillin# • Azidocillin • Penamecillin

Phenoxymethylpenicillin (V)#: Propicillin • Benzathine phenoxymethylpenicillin • Pheneticillin
Penems
Biapenem • Ertapenem • antipseudomonal (Doripenem • Imipenem • Meropenem) • Panipenem
4th (antips-)
Ceftobiprole • Ceftaroline fosamil
Aztreonam • Tigemonam • Carumonam • Tabtoxin
Combinations
Other
polymyxins/detergent (Colistin, Polymyxin B) • depolarizing (Daptomycin) • hydrolyze NAM-NAG (Lysozyme) • Gramicidin

M: BAC

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)
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