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Merck
CN

SML3834

Vorapaxar

≥98% (HPLC)

Synonym(s):

Ethyl [(3aR,4aR,8aR,9aS)-9(S)-[(E)-2-[5-(3-fluorophenyl)-2-pyridinyl]ethenyl]dodecahydro-1(R)-methyl-3-oxonaphtho[2,3-c]furan-6(R)-yl]carbamate, MK 5348, MK-5348, MK5348, SCH 530348, SCH-530348, SCH530348

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About This Item

Empirical Formula (Hill Notation):
C29H33FN2O4
CAS Number:
618385-01-6
Molecular Weight:
492.58
UNSPSC Code:
51111800
NACRES:
NA.77
MDL number:
MFCD16038876

Key Documents

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SMILES string

Fc1cc(ccc1)c2cnc(cc2)\C=C\[C@@H]3[C@H]4[C@@H](C[C@H]5[C@H]3CC[C@H](C5)NC(=O)OCC)C(=O)O[C@@H]4C

InChI key

ZBGXUVOIWDMMJE-QHNZEKIYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

Quality Level

100

Biochem/physiol Actions

Orally active, potent and selective thrombin receptor (PAR-1) antagonist with anti-platelet aggregation efficacy in vitro and in vivo.
Vorapaxar (MK-5348; SCH 530348) is an orally active, potent and selective thrombin receptor (PAR-1) antagonist with good selectivity over a panel of GPCRs, ion channels, and receptors, including PAR-2, PAR-3 and PAR-4. Vorapaxar inhibitis thrombin-induced calcium transient and thymidine incorporation in human coronary artery smoothmuscle cells (HCASMC; Ki = 1.1 and 13 nM, respectively), as well as aggregation in human platelet-rich plasma (PRP) induced by 10 nM thrombin or 15 μM haTRAP (IC50 = 47 and 25 nM, respectively), but not 20 μM ADP or 5 μM collagen. Oral administration (0.1 mg/kg to cynomolgus monkeys) prevents haTRAP-induced platelet aggregation ex vivo.

pictograms

Environment
GHS09

signalword

Warning

hcodes

H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000440026
0000440026
0000269623
0000269624
0000261952

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Vorapaxar proven to be a promising candidate for pulmonary fibrosis by intervening in the PAR1/JAK2/STAT1/3 signaling pathway-an experimental in vitro and vivo study
European Journal of Pharmacology, 943, 175438-175438 (2023)
Targeting senescent hepatocytes using the thrombomodulin-PAR1 inhibitor vorapaxar ameliorates NAFLD progression
Hepatology (2023)
Samuel Chackalamannil et al.
Journal of medicinal chemistry, 51(11), 3061-3064 (2008-05-02)
The discovery of an exceptionally potent series of thrombin receptor (PAR-1) antagonists based on the natural product himbacine is described. Optimization of this series has led to the discovery of 4 (SCH 530348), a potent, oral antiplatelet agent that is

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