Cefmetazole

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Cefmetazole
Cefmetazole.svg
Systematic (IUPAC) name
(6R,7S)-7-(2-(cyanomethylthio)acetamido)-7-methoxy-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a601206
Legal status
?
Identifiers
CAS number 56796-20-4 YesY
ATC code J01DC09
PubChem CID 42008
DrugBank DB00274
ChemSpider 38311 YesY
UNII 3J962UJT8H YesY
KEGG D00910 YesY
ChEBI CHEBI:3489 YesY
ChEMBL CHEMBL1201195 N
Chemical data
Formula C15H17N7O5S3 
Mol. mass 471.538 g/mol
 N (what is this?)  (verify)

Cefmetazole is a cephalosporin antibiotic, usually grouped with the second-generation cephalosporins.

Adverse effects[edit]

The chemical structure of cefmetazole, like that of several other cephalosporins, 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]

Spectrum of bacterial susceptibility[edit]

Cefmetazole is a broad-spectrum cephalosporin antimicrobial and has been effective in treating bacteria responsible for causing urinary tract and skin infections. The following represents MIC susceptibility data for a few medically significant microorganisms.

  • Bacteroides fragilis: 0.06 - >256 µg/ml
  • Clostridium difficile: 8 - >128 µg/ml
  • Staphylococcus aureus: 0.5 - 256 µg/ml (includes MRSA)

[2]

References[edit]

  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. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03. 
  2. ^ http://www.toku-e.com/Assets/MIC/Cefmetazole%20free%20acid.pdf