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CHEBI:131730 - cefatrizine

ChEBI IDCHEBI:131730
ChEBI Namecefatrizine
Stars
DefinitionA 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.
Last Modified13 February 2018
SubmitterKevin
DownloadsMolfile
FormulaC18H18N6O5S2
Net Charge0
Average Mass462.513
Monoisotopic Mass462.07801
SMILES[H][C@]12SCC(CSc3cnnn3)=C(C(=O)O)N1C(=O)[C@@]2([H])NC(=O)[C@H](N)c1ccc(O)cc1
InChIInChI=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
InChIKeyUOCJDOLVGGIYIQ-PBFPGSCMSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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).
antibacterial drug  A drug used to treat or prevent bacterial infections.
drug allergen  Any drug which causes the onset of an allergic reaction.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Applications:
antibacterial drug  A drug used to treat or prevent bacterial infections.
drug allergen  Any drug which causes the onset of an allergic reaction.
ChEBI Ontology
Outgoing Relation(s)
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  Source
cefatrizineWHO MedNet
cefatrizinaWHO MedNet
céfatrizineWHO MedNet
cefatrizinumWHO MedNet
Synonyms  Source
(7R)-7-(α-D-4-hydroxyphenylglycylamino)-3-(1H-1,2,3-triazol-4-ylthiomethyl)-3-cephem-4-carboxylic acidChEBI
SKF 60771ChemIDplus
antibiotic BL-S 640ChemIDplus
BLS 640ChemIDplus
BL-S640ChemIDplus
BL-S 640ChemIDplus
Manual XrefsDatabases
D02406KEGG DRUG
CefatrizineWikipedia
DE2316866Patent
DE2364192Patent
US3867380Patent
529DrugCentral
Registry NumbersSources
Reaxys:8172545Reaxys
CAS:51627-14-6KEGG DRUG
CAS:51627-14-6ChemIDplus
Citations