Cefmetazole
- J01DC09 (WHO)
- (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
- 56796-20-4 Y
- 42008
- DB00274 Y
- 38311 Y
- 3J962UJT8H
- D00910 Y
- CHEBI:3489 Y
- ChEMBL1201195 N
- DTXSID7022756
- Interactive image
- O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)CSCC#N)CSc3nnnn3C)C(=O)O
- 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
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. [citation needed]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.
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(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Glycopeptides Lipoglycopeptides |
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Lipopeptides |
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Polymyxins |
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Other |
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- Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
- Hydrolyze NAM-NAG
- Tyrothricin
- Isoniazid#
- Teixobactin
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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