vorapaxar   Click here for help

GtoPdb Ligand ID: 4047

Synonyms: SCH 530348 | SCH-530348 | SCH530348 | Zontivity®
Approved drug PDB Ligand
vorapaxar is an approved drug (FDA (2014))
Compound class: Synthetic organic
Comment: Vorapaxar is an orally active thrombin receptor (PAR1) antagonist based on the natural product himbacine [1], that is used as an anti-thrombosis drug.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 77.52
Molecular weight 492.24
XLogP 5.52
No. Lipinski's rules broken 1
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Canonical SMILES CCOC(=O)NC1CCC2C(C1)CC1C(C2C=Cc2ccc(cn2)c2cccc(c2)F)C(OC1=O)C
Isomeric SMILES CCOC(=O)N[C@@H]1CC[C@@H]2[C@@H](C1)C[C@@H]1[C@H]([C@H]2/C=C/c2ccc(cn2)c2cccc(c2)F)[C@H](OC1=O)C
InChI InChI=1S/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
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Summary of Clinical Use Click here for help
Approved to reduce the risk of thrombotic cardiovascular events in patients with a history of myocardial infarction (MI) or with peripheral arterial disease (PAD).
SARS-CoV-2 and COVID-19: Antagonism of PAR1 and the resulting anti-thrombotic action may be applicable to the management of pathological thrombosis and endotheliitis in patients with severe COVID-19 [2].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Vorapaxar is an antagonist of the protease-activated receptor-1 (PAR1) expressed on platelets. The effect is to inhibit thrombin-induced and thrombin receptor agonist peptide (TRAP)-induced platelet aggregation. Drug action reduces the formation of blood clots and reduces the risk of cardiovascular events and stroke. Due to its long receptor dissociation half-life of (~20 hours) it acts effectively in an irreversible fashion. Its very long elimination half-life, means it is long-acting, displaying significant inhibition of platelet aggregation for up to 4 weeks after discontinuation [3].
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