Cefoperazone

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Cefoperazone
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Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601206
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Pharmacokinetic data
ExcretionHepatic
Identifiers
  • (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
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Chemical and physical data
FormulaC25H27N9O8S2
Molar mass645.67 g·mol−1
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  • InChI=1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15-,16-,22-/m1/s1 checkY
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Cefoperazone is a third-generation cephalosporin antibiotic, marketed by Pfizer under the name Cefobid. It is one of few cephalosporin antibiotics effective in treating Pseudomonas bacterial infections which are otherwise resistant to these antibiotics.

It was patented in 1974 and approved for medical use in 1981.[1] Cefoperazone/sulbactam (Sulperazon) is a co-formulation with sulbactam.

Spectrum of bacterial susceptibility

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[2]

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 effect), due to inhibition of aldehyde dehydrogenase.[3]


References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 494. ISBN 9783527607495.
  2. ^ Page Module:Citation/CS1/styles.css has no content."Cefoperazone (Cefobid) - The Antimicrobial Index Knowledgebase - TOKU-E". antibiotics.toku-e.com.
  3. ^ Page Module:Citation/CS1/styles.css has no content.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.

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