CHEBI:73266 - fradafiban

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ChEBI Name fradafiban
ChEBI ID CHEBI:73266
Definition A pyrrolidinone that is pyrrolidin-2-one which is substituted at positions 3 and 5 by carboxymethyl and hydroxymethyl groups, respectively, and in which the hydrogen of the resulting alcoholic hydroxy group is replaced by a 4'-carbamimidoylbiphenyl-4-yl group (the S,S-diastereoisomer). A figrinogen receptor antagonist.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H21N3O4
Net Charge 0
Average Mass 367.39840
Monoisotopic Mass 367.15321
InChI InChI=1S/C20H21N3O4/c21-19(22)14-3-1-12(2-4-14)13-5-7-17(8-6-13)27-11-16-9-15(10-18(24)25)20(26)23-16/h1-8,15-16H,9-11H2,(H3,21,22)(H,23,26)(H,24,25)/t15-,16-/m0/s1
InChIKey IKZACQMAVUIGPY-HOTGVXAUSA-N
SMILES [H][C@@]1(COc2ccc(cc2)-c2ccc(cc2)C(N)=N)C[C@@H](CC(O)=O)C(=O)N1
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): platelet glycoprotein-IIb/IIIa receptor antagonist
Antagonist of platelet surface glycoprotein-IIb/IIIa which has a key role in hemostasis and thrombosis such as platelet adhesion and aggregation.
Application(s): platelet glycoprotein-IIb/IIIa receptor antagonist
Antagonist of platelet surface glycoprotein-IIb/IIIa which has a key role in hemostasis and thrombosis such as platelet adhesion and aggregation.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing fradafiban (CHEBI:73266) has role platelet glycoprotein-IIb/IIIa receptor antagonist (CHEBI:50433)
fradafiban (CHEBI:73266) is a carboxamidine (CHEBI:35359)
fradafiban (CHEBI:73266) is a monocarboxylic acid (CHEBI:25384)
fradafiban (CHEBI:73266) is a pyrrolidin-2-ones (CHEBI:74223)
Incoming lefradafiban (CHEBI:60634) has functional parent fradafiban (CHEBI:73266)
IUPAC Name
[(3S,5S)-5-{[(4'-carbamimidoylbiphenyl-4-yl)oxy]methyl}-2-oxopyrrolidin-3-yl]acetic acid
INNs Sources
fradafiban WHO MedNet
fradafibán WHO MedNet
fradafiban WHO MedNet
fradafibanum WHO MedNet
Synonyms Sources
(3S,5S)-5-(((4'-amidino-4-biphenylyl)oxy)methyl)-2-oxo-3-pyrrolidineacetic acid ChemIDplus
(3S-trans)-5-[[[4'-(aminoiminomethyl)[1,1'-biphenyl]-4-yl]oxy]methyl]-2-oxo-3-pyrrolidineacetic acid ChEBI
Registry Numbers Types Sources
148396-36-5 CAS Registry Number ChemIDplus
8585909 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10566068 PubMed citation Europe PMC
9286940 PubMed citation Europe PMC
9352399 PubMed citation Europe PMC
Last Modified
20 June 2013