CHEBI:60634 - lefradafiban

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ChEBI Name lefradafiban
ChEBI ID CHEBI:60634
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Anonymous
Secondary ChEBI IDs CHEBI:60715
Supplier Information
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Formula C23H25N3O6
Net Charge 0
Average Mass 439.46110
Monoisotopic Mass 439.17434
InChI InChI=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
InChIKey PGCFXITVMNNKON-ROUUACIJSA-N
SMILES COC(=O)C[C@@H]1C[C@@H](COc2ccc(cc2)-c2ccc(cc2)C(=N)NC(=O)OC)NC1=O
Roles Classification
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): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
léfradafiban WHO MedNet
lefradafibán WHO MedNet
lefradafiban ChemIDplus
lefradafibanum WHO MedNet
Synonyms Sources
(3S,5S)-5-[(4'-methoxycarbonylamidino-4-biphenylyl)-oxymethyl]-3-[(methoxycarbonyl)methyl]-2-pyrrolidinone ChEBI
3-pyrrolidineacetic acid, 5-[[[4'-[imino[(methoxycarbonyl) amino]methyl] [1,1'-biphenyl]-4-yl]oxy]methyl]-2-oxo-,methyl ester, (3S-trans) ChEBI
FP-007SE ChEBI
Registry Numbers Types Sources
14535302 Reaxys Registry Number Reaxys
149503-79-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10566070 PubMed citation Europe PMC
10886122 PubMed citation Europe PMC
11102255 PubMed citation Europe PMC
11250974 PubMed citation Europe PMC
21081137 PubMed citation Europe PMC
9286940 PubMed citation Europe PMC
Last Modified
30 March 2015