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Cefmetazole

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Chemical compound Pharmaceutical compound
Cefmetazole
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa601206
ATC code
Identifiers
IUPAC name
  • (6R,7S)-7-(2-(cyanomethylthio)acetamido)-7-methoxy-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.054.877 Edit this at Wikidata
Chemical and physical data
FormulaC15H17N7O5S3
Molar mass471.53 g·mol
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(\CS12(OC)NC(=O)CSCC#N)CSc3nnnn3C)C(=O)O
InChI
  • InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1
  • Key:SNBUBQHDYVFSQF-HIFRSBDPSA-N
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Cefmetazole is a cephamycin antibiotic, usually grouped with the second-generation cephalosporins.

Adverse effects

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, due to inhibition of aldehyde dehydrogenase.

Spectrum of bacterial susceptibility

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.

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. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.
  2. "Cefmetazole, free acid Susceptibility and Concentration Range (μg/ml) Minimum Inhibitory Concentration (MIC) Data" (PDF). The Antimicrobial Index. TOKU-E. 6 January 2020.
Antibacterials active on the cell wall and envelope (J01C-J01D)
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking: Ramoplanin
Intracellular
Other
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