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CHEBI:60634 - lefradafiban

ChEBI IDCHEBI:60634
ChEBI Namelefradafiban
Stars
DefinitionA member of the class of pyrrolidin-2-ones that is pyrrolidin-2-one in which the 3-pro-S-hydrogen is substituted by a 2-methoxy-2-oxoethyl group, while the 5-pro-S-hydrogen is substituted by a ({4'-[N-(methoxycarbonyl)carbamimidoyl]biphenyl-4-yl}oxy)methyl group. It is an orally active prodrug of fradafiban, a figrinogen receptor antagonist.
Secondary ChEBI IDCHEBI:60715
Last Modified30 March 2015
DownloadsMolfile
FormulaC23H25N3O6
Net Charge0
Average Mass439.468
Monoisotopic Mass439.17434
SMILES[H][C@@]1(COc2ccc(-c3ccc(C(=N)NC(=O)OC)cc3)cc2)C[C@@H](CC(=O)OC)C(=O)N1
InChIInChI=1S/C23H25N3O6/c1-30-20(27)12-17-11-18(25-22(17)28)13-32-19-9-7-15(8-10-19)14-3-5-16(6-4-14)21(24)26-23(29)31-2/h3-10,17-18H,11-13H2,1-2H3,(H,25,28)(H2,24,26,29)/t17-,18-/m0/s1
InChIKeyPGCFXITVMNNKON-ROUUACIJSA-N
Roles Classification
Biological Role:
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.
Applications:
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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.
ChEBI Ontology
Outgoing Relation(s)
lefradafiban (CHEBI:60634) has functional parent fradafiban (CHEBI:73266)
lefradafiban (CHEBI:60634) has role platelet glycoprotein-IIb/IIIa receptor antagonist (CHEBI:50433)
lefradafiban (CHEBI:60634) has role prodrug (CHEBI:50266)
lefradafiban (CHEBI:60634) is a methyl ester (CHEBI:25248)
lefradafiban (CHEBI:60634) is a pyrrolidin-2-ones (CHEBI:74223)
IUPAC Names 
methyl {(3S,5S)-5-[({4'-[N-(methoxycarbonyl)carbamimidoyl]([1,1'-biphenyl]-4-yl)}oxy)methyl]-2-oxopyrrolidin-3-yl}acetate
methyl {(3S,5S)-5-[({4'-[N-(methoxycarbonyl)carbamimidoyl]biphenyl-4-yl}oxy)methyl]-2-oxopyrrolidin-3-yl}acetate
INNs  Source
lefradafibanChemIDplus
lefradafibanumWHO MedNet
léfradafibanWHO MedNet
lefradafibánWHO MedNet
Synonyms  Source
3-pyrrolidineacetic acid, 5-[[[4'-[imino[(methoxycarbonyl) amino]methyl] [1,1'-biphenyl]-4-yl]oxy]methyl]-2-oxo-,methyl ester, (3S-trans)ChEBI
(3S,5S)-5-[(4'-methoxycarbonylamidino-4-biphenylyl)-oxymethyl]-3-[(methoxycarbonyl)methyl]-2-pyrrolidinoneChEBI
FP-007SEChEBI
Registry NumbersSources
Reaxys:14535302Reaxys
CAS:149503-79-7ChemIDplus
Citations