CHEBI:3489 - cefmetazole

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ChEBI Name cefmetazole
ChEBI ID CHEBI:3489
Definition A second-generation cephalosporin antibiotic having N1-methyltetrazol-5-ylthiomethyl, {[(cyanomethyl)sulfanyl]acetyl}amino and methoxy side-groups at positions 3, 7β and 7α respectively of the parent cephem bicyclic structure.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H17N7O5S3
Net Charge 0
Average Mass 471.53400
Monoisotopic Mass 471.045
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
InChIKey SNBUBQHDYVFSQF-HIFRSBDPSA-N
SMILES [H][C@]12SCC(CSc3nnnn3C)=C(N1C(=O)[C@]2(NC(=O)CSCC#N)OC)C(O)=O
Roles Classification
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cefmetazole (CHEBI:3489) has role antibacterial drug (CHEBI:36047)
cefmetazole (CHEBI:3489) is a cephalosporin (CHEBI:23066)
cefmetazole (CHEBI:3489) is conjugate acid of cefmetazole(1−) (CHEBI:52439)
Incoming cefmetazole(1−) (CHEBI:52439) is conjugate base of cefmetazole (CHEBI:3489)
IUPAC Name
7β-{[(cyanomethyl)sulfanyl]acetamido}-7α-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic acid
INNs Sources
cefmetazole KEGG DRUG
cefmetazolo DrugBank
cefmetazolum DrugBank
Synonym Source
(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 IUPAC
Manual Xrefs Databases
539 DrugCentral
C08103 KEGG COMPOUND
Cefmetazole Wikipedia
D00910 KEGG DRUG
DB00274 DrugBank
LSM-5594 LINCS
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Registry Numbers Types Sources
5406306 Beilstein Registry Number Beilstein
56796-20-4 CAS Registry Number KEGG COMPOUND
56796-20-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10109799 PubMed citation Europe PMC
23140947 PubMed citation Europe PMC
23705013 PubMed citation Europe PMC
2416589 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
8452349 PubMed citation Europe PMC
Last Modified
13 March 2018