Lefradafiban

Status : investigational

Category

Antianginal Agents

Description

Lefradafiban is an oral platelet glycoprotein IIb/IIIa receptor antagonist being investigated in the treatment of angina.

Used

For the treatment of unstable angina.

Mechanism Of Action

GPIIb/IIIa inhibitors, such as lefradafiban, block the final common pathway of platelet aggregation.

Pharmacodynamics

Lefradafiban, an orally active prodrug of fradafiban, is a novel glycoprotein (IIb/IIIa) inhibitor for the treatment of unstable angina. Development was discontinued in 2000 due to lack of efficacy.

Chemical Classification

This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Biphenyls and derivatives

Organic compounds

Benzenoids

Benzene and substituted derivatives

Biphenyls and derivatives

Calculated Property

kind Value Source
logP 2.57 ALOGPS
logS -4.7 ALOGPS
Water Solubility 8.80e-03 g/l ALOGPS
logP 1.66 ChemAxon
IUPAC Name methyl 2-[(3S,5S)-5-(4-{4-[(1Z)-amino[(methoxycarbonyl)imino]methyl]phenyl}phenoxymethyl)-2-oxopyrrolidin-3-yl]acetate ChemAxon
Traditional IUPAC Name methyl 2-[(3S,5S)-5-(4-{4-[(1Z)-amino[(methoxycarbonyl)imino]methyl]phenyl}phenoxymethyl)-2-oxopyrrolidin-3-yl]acetate ChemAxon
Molecular Weight 439.4611 ChemAxon
Monoisotopic Weight 439.174335547 ChemAxon
SMILES COC(=O)C[C@@H]1C[C@@H](COC2=CC=C(C=C2)C2=CC=C(C=C2)C(N)=NC(=O)OC)NC1=O ChemAxon
Molecular Formula C23H25N3O6 ChemAxon
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 ChemAxon
InChIKey InChIKey=PGCFXITVMNNKON-ROUUACIJSA-N ChemAxon
Polar Surface Area (PSA) 129.31 ChemAxon
Refractivity 115.47 ChemAxon
Polarizability 47.13 ChemAxon
Rotatable Bond Count 9 ChemAxon
H Bond Acceptor Count 6 ChemAxon
H Bond Donor Count 2 ChemAxon
pKa (strongest acidic) 14 ChemAxon
pKa (strongest basic) 0.71 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 3 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 1 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Integrin alpha-IIb : in Human
  • Integrin beta-3 : in Human