Cefoperazone

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Cefoperazone
Cefoperazone.svg
Cefoperazone ball-and-stick.png
Systematic (IUPAC) name
(6R,7R)-7-[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a601206
Legal status ?
Pharmacokinetic data
Excretion Hepatic
Identifiers
CAS number 62893-19-0 YesY
ATC code J01DD12 QJ51DD12
PubChem CID 44185
DrugBank DB01329
ChemSpider 40206 YesY
UNII 7U75I1278D YesY
KEGG D07645 YesY
ChEMBL CHEMBL507674 YesY
Chemical data
Formula C25H27N9O8S2 
Mol. mass 645.67 g/mol
 YesY (what is this?)  (verify)

Cefoperazone is a third-generation cephalosporin antibiotic, marketed by Pfizer under the name Cefobid, and also marked by Pharco B International under the name Cefazone and also marketed by Sigmatec Pharmaceuticals under the name Cefoperazone. 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. Gepach International markets this combination of cefoperazone with sulbactam under the brand name Bacperazone.

Spectrum of bacterial susceptibility[edit]

Cefoperazone has a broad spectrum of activity and has been used to target bacteria responsible for causing infections of the respiratory and urinary tract, skin, and the female genital tract. The following represents MIC susceptibility data for a few medically significant microorganisms.

  • Haemophilus influenzae: 0.12 - 0.25 µg/ml
  • Staphylococcus aureus: 0.125 - 32 µg/ml
  • Streptococcus pneumoniae: ≤0.007 - 1 µg/ml

[1] [2]


Adverse effects[edit]

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.[3]

References[edit]

  1. ^ http://antibiotics.toku-e.com/antimicrobial_462_1.html
  2. ^ http://www.toku-e.com/Assets/MIC/Cefoperazone%20sodium.pdf
  3. ^ 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. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.