VPX

ethyl [(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl}-1-methyl-3-oxododecahydronaphtho[2,3-c]fur an-6-yl]carbamate

Created:	2012-08-23
Last modified:	2020-06-05

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1 entries where VPX is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	69
Chiral Atom Count	7
Bond Count	73
Aromatic Bond Count	12

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Chemical Component Summary
Name	ethyl [(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl}-1-methyl-3-oxododecahydronaphtho[2,3-c]fur an-6-yl]carbamate
Synonyms	vorapaxar
Systematic Name (OpenEye OEToolkits)	ethyl N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl]-1-methyl-3-oxidanylidene-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-1H-benzo[f][2]benzofuran-6-yl]carbamate
Formula	C₂₉ H₃₃ F N₂ O₄
Molecular Weight	492.582
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	Fc1cccc(c1)c2ccc(nc2)\C=C\C4C3C(CC(NC(=O)OCC)CC3)CC5C(=O)OC(C45)C
SMILES	CACTVS	3.370	CCOC(=O)N[CH]1CC[CH]2[CH](C1)C[CH]3[CH]([CH](C)OC3=O)[CH]2C=Cc4ccc(cn4)c5cccc(F)c5
SMILES	OpenEye OEToolkits	1.7.6	CCOC(=O)NC1CCC2C(C1)CC3C(C2C=Cc4ccc(cn4)c5cccc(c5)F)C(OC3=O)C
Canonical SMILES	CACTVS	3.370	CCOC(=O)N[C@@H]1CC[C@@H]2[C@@H](C1)C[C@@H]3[C@@H]([C@@H](C)OC3=O)[C@H]2\C=C\c4ccc(cn4)c5cccc(F)c5
Canonical SMILES	OpenEye OEToolkits	1.7.6	CCOC(=O)N[C@@H]1CC[C@@H]2[C@@H](C1)C[C@@H]3[C@H]([C@H]2/C=C/c4ccc(cn4)c5cccc(c5)F)[C@H](OC3=O)C
InChI	InChI	1.03	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
InChIKey	InChI	1.03	ZBGXUVOIWDMMJE-QHNZEKIYSA-N

Drug Info: DrugBank

DrugBank ID	DB09030
Name	Vorapaxar
Groups	approved
Description	Vorapaxar is a tricyclic himbacine-derived selective inhibitor of protease activated receptor (PAR-1) indicated for reducing the incidence of thrombotic cardiovascular events in patients with a history of myocardial infarction (MI) or with peripheral arterial disease (PAD). By inhibiting PAR-1, a thrombin receptor expressed on platelets, vorapaxar prevents thrombin-related platelet aggregation.
Synonyms	Vorapaxar sulfate Carbamic acid, [(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 Carbamic acid, N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(E)-2-[5-(3-fluorophenyl)-2-pyridinyl]ethenyl]dodecahydro-1-methyl-3-oxonaphtho[2,3-c]furan-6-yl]-, ethyl ester [(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-Fluorophényl)-2-pyridinyl]vinyl}-1-méthyl-3-oxododécahydronaphto[2,3-c]furan-6-yl]carbamate d'éthyle Ethyl N-[(3R,3aS,4S,4aR,7R,8aR,9aR)-4-[(E)-2-[5-(3-fluorophenyl)-2-pyridyl]vinyl]-3-methyl-1-oxo-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-3H-benzo[f]isobenzofuran-7-yl]carbamate Vorapaxar
Brand Names	Zontivity
Indication	Vorapaxar is indicated for the reduction of thrombotic cardiovascular events in patients with a history of myocardial infarction (MI) or peripheral arterial disease (PAD). It is usually co-administered with acetylsalicylic acid (ASA) and/or clopidogrel, and should therefore be administered as an addition to these medications as it has not been studied alone.
Categories	Anticoagulants Antiplatelet agents Blood and Blood Forming Organs Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates (strength unknown) Cytochrome P-450 Substrates Hematologic Agents P-glycoprotein inhibitors Platelet Aggregation Inhibitors Excl. Heparin Protease-activated Receptor-1 Antagonist Protease-activated Receptor-1 Antagonists Receptor, PAR-1, antagonists & inhibitors Receptors, Thrombin, antagonists & inhibitors
ATC-Code	B01AC26
CAS number	618385-01-6

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Proteinase-activated receptor 1	MGPRRLLLVAACFSLCGPLLSARTRARRPESKATNATLDPRSFLLRNPND...	unknown	antagonist
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 2J2	MLAAMGSLAAALWAVVHPRTLLLGTVAFLLAADFLKRRRPKNYPPGPWRL...	unknown	substrate
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682