CHEBI:131730 - cefatrizine

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ChEBI Name cefatrizine
ChEBI ID CHEBI:131730
Definition A cephalosporin compound having (1H-1,2,3-triazol-4-ylsulfanyl)methyl and [(2R)-2-amino-2-(4-hydroxyphenyl)]acetamido side-groups. An antibacterial drug first prepared in the 1970s, it has more recently been found to be an inhibitor of eukaryotic elongation factor-2 kinase (eEF2K), which is known to regulate apoptosis, autophagy and ER stress in many types of human cancers.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kevin
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Formula C18H18N6O5S2
Net Charge 0
Average Mass 462.506
Monoisotopic Mass 462.078
InChI InChI=1S/C18H18N6O5S2/c19-12(8-1-3-10(25)4-2-8)15(26)21-13-16(27)24-14(18(28)29)9(7-31-17(13)24)6-30-11-5-20-23-22-11/h1-5,12-13,17,25H,6-7,19H2,(H,21,26)(H,28,29)(H,20,22,23)/t12-,13-,17-/m1/s1
InChIKey UOCJDOLVGGIYIQ-PBFPGSCMSA-N
SMILES N=1NC=C(N1)SCC2=C(N3[C@](SC2)([C@@](C3=O)(NC([C@H](N)C=4C=CC(=CC4)O)=O)[H])[H])C(=O)O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
EC 2.7.11.20 (elongation factor 2 kinase) inhibitor
Any EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of elongation factor 2 kinase (EC 2.7.11.20).
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 cefatrizine (CHEBI:131730) has role antibacterial drug (CHEBI:36047)
cefatrizine (CHEBI:131730) has role EC 2.7.11.20 (elongation factor 2 kinase) inhibitor (CHEBI:131734)
cefatrizine (CHEBI:131730) is a amino acid amide (CHEBI:22475)
cefatrizine (CHEBI:131730) is a carboxylic acid (CHEBI:33575)
cefatrizine (CHEBI:131730) is a cephalosporin (CHEBI:23066)
cefatrizine (CHEBI:131730) is a phenols (CHEBI:33853)
cefatrizine (CHEBI:131730) is a semisynthetic derivative (CHEBI:72588)
cefatrizine (CHEBI:131730) is a triazoles (CHEBI:35727)
IUPAC Name
(6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-[(1H-1,2,3-triazol-4-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
INNs Sources
cefatrizina WHO MedNet
céfatrizine WHO MedNet
cefatrizine WHO MedNet
cefatrizinum WHO MedNet
Synonyms Sources
(7R)-7-(α-D-4-hydroxyphenylglycylamino)-3-(1H-1,2,3-triazol-4-ylthiomethyl)-3-cephem-4-carboxylic acid ChEBI
antibiotic BL-S 640 ChemIDplus
BL-S 640 ChemIDplus
BL-S640 ChemIDplus
BLS 640 ChemIDplus
SKF 60771 ChemIDplus
Manual Xrefs Databases
529 DrugCentral
Cefatrizine Wikipedia
D02406 KEGG DRUG
DE2316866 Patent
DE2364192 Patent
US3867380 Patent
View more database links
Registry Numbers Types Sources
51627-14-6 CAS Registry Number ChemIDplus
51627-14-6 CAS Registry Number KEGG DRUG
8172545 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
1137381 PubMed citation Europe PMC
2329468 PubMed citation Europe PMC
23894823 PubMed citation Europe PMC
239917 PubMed citation Europe PMC
26776155 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
3915469 PubMed citation Europe PMC
6660858 PubMed citation Europe PMC
813573 PubMed citation Europe PMC
Last Modified
13 February 2018