Cefmetazole

Cefmetazole
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601206
ATC code	J01DC09 (WHO) ;
Identifiers
	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;
CAS Number	56796-20-4 ;
PubChem CID	42008;
DrugBank	DB00274 ;
ChemSpider	38311 ;
UNII	3J962UJT8H;
KEGG	D00910 ;
ChEBI	CHEBI:3489 ;
ChEMBL	ChEMBL1201195 ;
CompTox Dashboard (EPA)	DTXSID7022756 ;
ECHA InfoCard	100.054.877
Chemical and physical data
Formula	C15H17N7O5S3
Molar mass	471.53 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:SNBUBQHDYVFSQF-HIFRSBDPSA-N ;
	(verify)

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.^[1]

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)^[2]

References

^ 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.
^ "Cefmetazole, free acid Susceptibility and Concentration Range (μg/ml) Minimum Inhibitory Concentration (MIC) Data" (PDF). The Antimicrobial Index. TOKU-E. 6 January 2020.

[Goldfrank-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.

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