618385-01-6

Basic information

• Product Name: Vorapaxar
• Synonyms: Vorapaxar;Vorapaxar (SCH 530348);[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(1E)-2-[5-(3-Fluorophenyl)-2-pyridinyl]ethenyl]dodecahydro-1-methyl-3-oxonaphtho[2,3-c]furan-6-yl]-carbamic acid ethyl ester;Voarapaxar;Carbamic acid, N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(1E)-2-[5-(3-fluorophenyl)-2-pyridinyl]ethenyl]dodecahydro-1-methyl-3-oxonaphtho[2,3-c]furan-6-yl]-, ethyl ester;Ethyl [(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-fluorophenyl)-2-pyridinyl]vinyl}-1-methyl-3-oxododecahydronaphtho[2,3-c]furan-6-yl]carbamate;[(1R,3AR,4aR,6R,8aR,9S,9aS)-9-[(1E)-2-[5-(3-fluorophenyl)-2-pyridinyl]ethenyl]dodecahydro-1-me
• CAS NO: 618385-01-6
• Molecular Formula: C29H33FN2O4
• Molecular Weight: 492.5817232
• Product Categories: API
• Mol File: 618385-01-6.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 676 °C at 760 mmHg
• Flash Point: 362.632 °C
• Appearance: /
• Density: 1.25 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.594
• Solubility: ≥24.65 mg/mL in DMSO; insoluble in H2O; ≥10.64 mg/mL in EtOH with ultrasonic
• PKA: 12.49±0.60(Predicted)
• CAS DataBase Reference: Vorapaxar(CAS DataBase Reference)
• NIST Chemistry Reference: Vorapaxar(618385-01-6)
• EPA Substance Registry System: Vorapaxar(618385-01-6)

Safety Data

• Hazardous Substances Data: 618385-01-6(Hazardous Substances Data)

Usage

Description

Vorapaxar is an orally bioavailable competitive antagonist of the proteinase-activated receptor (PAR1; Ki = 8.1 nM), also known as the thrombin receptor. It is selective for PAR1 over other PARs, as well as a number of GPCRs, ion channels, and receptors. It inhibits platelet aggregation induced by thrombin and haTRAP (IC50s = 47 and 25 nM, respectively). Vorapaxar (0.1 mg/kg, i.v.) completely inhibits platelet aggregation in cynomolgus monkeys ex vivo. Formulations containing vorapaxar are used in the prevention of thrombotic cardiovascular events.

Definition

ChEBI: A carbamate ester that is the ethyl ester of [(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethyny }-1-methyl-3-oxododecahydronaphtho[2,3-c]furan-6-yl]carbamic acid. A protease-activated receptor-1 antagonist used (as its sulfate salt) for the reduction of thrombotic cardiovascular events in patients with a history of myocardial infarction MI) or with peripheral arterial disease. It has been shown to reduce the rate of a combined endpoint of cardiovascular death, MI, stroke and urgent coronary revascularisation.

references

[1]. chackalamannil s & xia, y. thrombin receptor (par-1) antagonists as novel antithrombotic agents. expert opinion on therapeutic patents, 2006.16:493-505.[2]. chackalamannil s, wang y, greenlee w j et al. 2008. discovery of a novel, orally active himbacine-based thrombin receptor antagonist (sch 530348) with potent antiplatelet activity. j med chem, 2008,51: 3061-3064.

InChI:InChI=1/C29H33FN2O4/c1-3-35-29(34)32-23-10-11-24-20(14-23)15-26-27(17(2)36-28(26)33)25(24)12-9-22-8-7-19(16-31-22)18-5-4-6-21(30)13-18/h4-9,12-13,16-17,20,23-27H,3,10-11,14-15H2,1-2H3,(H,32,34)/b12-9+/t17-,20+,23-,24-,25+,26-,27+/m1/s1