Structure via PubChem · Public domain (PubChem)
cefmetazole
Sign in to saveAlso known as U-72791, (6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, Cefmetazolo, Cefmetazolum
Cefmetazole is a cephamycin antibiotic, usually grouped with the second-generation cephalosporins.
Chemical data
- Formula
- C15H17N7O5S3
- Molecular weight
- 471.5 g/mol
- IUPAC name
- (6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
- InChIKey
- SNBUBQHDYVFSQF-HIFRSBDPSA-N
- XLogP
- -0.6
- Polar surface area
- 239 Ų
- H-bond donors
- 2
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1989
- Admin. routes
- parenteral
- Indications
- osteomyelitis, colorectal neoplasm, bacterial disease
via ChEMBL · EBI
Research
842 papers- [Cefmetazole].Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic] · 1993
- Cefmetazole sodium: pharmacology, pharmacokinetics, and clinical trials.Pharmacotherapy · 1991
- Cefmetazole (CS-1170), a "new" cephamycin with a decade of clinical experience.Diagnostic microbiology and infectious disease · 1989
- Cefmetazole for extended-spectrum β-lactamase-producing Enterobacteriaceae in pediatric pyelonephritis.Pediatrics international : official journal of the Japan Pediatric Society · 2019
- Cefmetazole Resistance Mechanism for Escherichia Coli Including ESBL-Producing Strains.Infection and drug resistance · 2022
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 471.045
- Has use
- medication
Show 7 more facts
- Commons category
- Cefmetazole
- chemical formula
- C₁₅H₁₇N₇O₅S₃
- subject has role
- bactericide
- canonical SMILES
- CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
- isomeric SMILES
- CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
- World Health Organisation international non-proprietary name
- cefmetazole
- defined daily dose
- 4
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Adverse effects
- Spectrum of bacterial susceptibility
- References
Cefmetazole is a cephamycin antibiotic, usually grouped with the second-generation cephalosporins.
__TOC__ ==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.
Excerpted from Wikipedia’s “cefmetazole” article, available under the CC BY-SA 4.0 licence.
Available in 10 languages
via Wikidata sitelinks · CC0