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Cefoperazone
Systematic (IUPAC) name
(6R,7S)-7-{[2-[(4-ethyl-2,3-dioxo-piperazine-1-
carbonyl)amino]-2-(4-hydroxyphenyl)acetyl}amino]-
3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-
1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Identifiers
CAS number 62893-19-0
ATC code J01DD12 QJ51DA32
PubChem 44185
ChemSpider 40206
Chemical data
Formula C 25H27N9O8S2  
Mol. mass 645.67 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion Hepatic
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?
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Cefoperazone is a third generation cephalosporin antibiotic, marketed by Pfizer under the name Cefobid, and also marked by pharco B international under the name of Cefazone. It is one of few cephalosporin antibiotics effective in treating Pseudomonas bacterial infections which are otherwise resistant to these antibiotics.

Cefina-SB is a combination of sulbactam and cefoperazone. Cefoperazone exerts its bactericidal effect by inhibiting the bacterial cell wall synthesis, and sulbactam acts as a beta-lactamase inhibitor, to increase the antibacterial activity of cefoperazone against beta-lactamase producing organisms. In some countries, the combination is sold as Sulperazone.

Adverse effects

Cefoperazone contains an N-methylthiotetrazole (NMTT or 1-MTT) side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.[1]

References

  1. ^ Stork CM (2006). "Antibiotics, antifungals, and antivirals". in Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. pp. 847. ISBN 0-07-143763-0. http://books.google.com/books?id=cvJuLqBxGUcC&pg=PA847. Retrieved 2009-07-03.  


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