| Identification | Back Directory | [Name]
Vorapaxar | [CAS]
618385-01-6 | [Synonyms]
CS-1663
CS-2015
MK-5348
Vorapaxar
Voarapaxar
Vorapaxar (SCH 530348)
[(1R,3AR,4aR,6R,8aR,9S,9aS)-9-[(1E)-2-[5-(3-fluorophenyl)-2-pyridinyl]ethenyl]dodecahydro-1-me
ethyl((1R,3aR,4aR,8aR,9aS)-9-((E)-2-(5-(3-fluorophenyl)pyridin-2-yl)vinyl)-1-methyl-3-oxododecahydronaphtho[2,3-c]furan-6-yl)carbamate
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-methyl-3-oxonaphtho[2,3-c]furan-6-yl]-carbamic acid ethyl ester
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 | [Molecular Formula]
C29H33FN2O4 | [MDL Number]
MFCD16038876 | [MOL File]
618385-01-6.mol | [Molecular Weight]
492.582 |
| Chemical Properties | Back Directory | [Boiling point ]
676.0±55.0 °C(Predicted) | [density ]
1.24±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20° C | [solubility ]
≥24.65 mg/mL in DMSO; insoluble in H2O; ≥10.64 mg/mL in EtOH with ultrasonic | [form ]
solid | [pka]
12.49±0.60(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Description]
Vorapaxar is an orally bioavailable competitive antagonist of the proteinase-activated receptor (PAR1; Ki = 8.1 nM), also known as the thrombin receptor.1 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 (Item No. 13188) 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. | [Uses]
Vorapaxar (SCH 530348), an antiplatelet agent, is a selective, orally active, and competitive thrombin receptor protease-activated receptor (PAR-1) antagonist (Ki=8.1 nM). Vorapaxar (SCH 530348) inhibits thrombin receptor-activating peptide (TRAP)-induced platelet aggregation in a dose-dependent manner[1]. | [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. | [IC 50]
PAR1: 8.1 nM (Ki) | [storage]
Store at -20° C | [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. |
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