Cefmetazole

{{Short description|Chemical compound}}

{{Drugbox

|image2=Cefmetazole 3D.png

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 460023468

| 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

| image = Cefmetazole.svg

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| Drugs.com = {{drugs.com|international|cefmetazole}}

| MedlinePlus = a601206

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 56796-20-4

| ATC_prefix = J01

| ATC_suffix = DC09

| PubChem = 42008

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00274

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 38311

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 3J962UJT8H

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00910

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 3489

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1201195

| C=15 | H=17 | N=7 | O=5 | S=3

| smiles = O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)CSCC#N)CSc3nnnn3C)C(=O)O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SNBUBQHDYVFSQF-HIFRSBDPSA-N

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

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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.{{cite book | vauthors = Stork CM |veditors=Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA |title=Goldfrank's toxicologic emergencies |chapter=Antibiotics, antifungals, and antivirals |chapter-url=https://books.google.com/books?id=cvJuLqBxGUcC&pg=PA847 |publisher=McGraw-Hill |location=New York |year=2006 |pages=847 |isbn=0-07-143763-0 |access-date=2009-07-03}}

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. {{cn|date=January 2023}}The following represents MIC susceptibility data for a few medically significant microorganisms.

  • Bacteroides fragilis: 0.06 - >256 μg/ml
  • Clostridioides difficile: 8 - >128 μg/ml
  • Staphylococcus aureus: 0.5 - 256 μg/ml (includes MRSA){{cite web | url = http://www.toku-e.com/Assets/MIC/Cefmetazole%20free%20acid.pdf | title = Cefmetazole, free acid Susceptibility and Concentration Range (μg/ml) Minimum Inhibitory Concentration (MIC) Data | work = The Antimicrobial Index | publisher = TOKU-E | date = 6 January 2020 }}

References