Cefmetazole

Cefmetazole

File: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
Identifiers
CAS Number	56796-20-4 Y
ATC code	J01DC09 (WHO)
PubChem	CID: 42008
DrugBank	DB00274 Y
ChemSpider	38311 Y
UNII	3J962UJT8H Y
KEGG	D00910 Y
ChEBI	CHEBI:3489 Y
ChEMBL	CHEMBL1201195 N
Chemical data
Formula	C15H17N7O5S3
Molecular mass	471.538 g/mol
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@]2(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 Y Key:SNBUBQHDYVFSQF-HIFRSBDPSA-N Y
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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 (Antabuse®), 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.

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