CHEBI:3499 - cefotetan

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ChEBI Name cefotetan
ChEBI ID CHEBI:3499
Definition A semi-synthetic second-generation cephamycin antibiotic with [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl, methoxy and {[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl}amino groups at the 3, 7α, and 7β positions, respectively, of the cephem skeleton. It is resistant to a wide range of β-lactamases and is active against a broad spectrum of aerobic and anaerobic Gram-positive and Gram-negative microorganisms.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:558729
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Formula C17H17N7O8S4
Net Charge 0
Average Mass 575.61900
Monoisotopic Mass 575.002
InChI InChI=1S/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/b12-6-/t13?,15-,17+/m1/s1
InChIKey SRZNHPXWXCNNDU-IXOPCIAXSA-N
SMILES [H][C@]12SCC(CSc3nnnn3C)=C(N1C(=O)[C@]2(NC(=O)C1SC(S1)=C(C(N)=O)C(O)=O)OC)C(O)=O
Roles Classification
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
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.
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ChEBI Ontology
Outgoing cefotetan (CHEBI:3499) has role antibacterial drug (CHEBI:36047)
cefotetan (CHEBI:3499) is a cephamycin (CHEBI:55429)
cefotetan (CHEBI:3499) is conjugate acid of cefotetan(2−) (CHEBI:59358)
Incoming cefotetan(2−) (CHEBI:59358) is conjugate base of cefotetan (CHEBI:3499)
IUPAC Names
(6R,7S)-7-({[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl}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
7β-({[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl}amino)-7α-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-3,4-didehydrocepham-4-carboxylic acid
INNs Sources
cefotetan ChemIDplus
cefotetanum ChemIDplus
Synonyms Sources
(6R,7S)-7-(4-(carbamoylcarboxymethylene)-1,3-dithiethane-2-carboxamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5- yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2- carboxylic acid ChemIDplus
cefotetan ChEMBL
Cefotetan KEGG COMPOUND
Manual Xrefs Databases
547 DrugCentral
C06886 KEGG COMPOUND
Cefotetan Wikipedia
D00260 KEGG DRUG
DB01330 DrugBank
DE2824559 Patent
LSM-5961 LINCS
US4263432 Patent
View more database links
Registry Numbers Types Sources
5697364 Beilstein Registry Number Beilstein
5697364 Reaxys Registry Number Reaxys
69712-56-7 CAS Registry Number KEGG COMPOUND
69712-56-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17664321 PubMed citation ChEMBL
29017833 PubMed citation Europe PMC
Last Modified
13 March 2018