Identification

Name
Vorapaxar
Accession Number
DB09030  (DB05692)
Type
Small Molecule
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.

Structure
Thumb
Synonyms
  • [(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
  • 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
  • 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
External IDs
MFCD16038876 / SCH 530348 / SCH-530348 / SCH530348 / ZCE93644N2
Product Ingredients
IngredientUNIICASInChI Key
Vorapaxar SulfateIN66038E6C705260-08-8NQRYCIGCIAWEIC-CKLVGUEFSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ZontivityTablet2.5 mgOralAralez Pharmaceuticals Trading DacNot applicableNot applicableCanada
ZontivityTablet, film coated2.08 mg/1OralMerck Sharp & Dohme Limited2014-05-08Not applicableUs
ZontivityTablet, film coated2.08 mg/1OralAralez Pharmaceuticals Us Inc.2014-05-08Not applicableUs
Categories
UNII
ZCE93644N2
CAS number
618385-01-6
Weight
Average: 492.5817
Monoisotopic: 492.242435759
Chemical Formula
C29H33FN2O4
InChI Key
ZBGXUVOIWDMMJE-QHNZEKIYSA-N
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
IUPAC Name
N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl]-1-methyl-3-oxo-dodecahydronaphtho[2,3-c]furan-6-yl]ethoxycarboximidic acid
SMILES
[H]\C(=C(\[H])[[email protected]]1([H])[[email protected]]2([H])[[email protected]@]([H])(C)OC(=O)[[email protected]]2([H])C[[email protected]]2([H])C[[email protected]@]([H])(CC[[email protected]@]12[H])N=C(O)OCC)C1=NC=C(C=C1)C1=CC(F)=CC=C1

Pharmacology

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.

Structured Indications
Pharmacodynamics
Not Available
Mechanism of action

Vorapaxar inhibits platelet aggregation through the reversible antagonism of protease-activated receptor 1 (PAR-1), also known as thrombin receptor. PARs are a family of G-protein coupled receptors highly expressed on platelets and activated by serine protease activity of thrombin to mediate thrombotic response. By blocking PAR-1 activating, vorapaxar inhibits thrombin-induced platelet aggregation and thrombin receptor agonist peptide (TRAP)-induced platelet aggregation. Vorapaxar does not inhibit platelet aggregation induced by other agonists such as adenosine diphosphate (ADP), collagen or a thromboxane mimetic.

TargetActionsOrganism
AProteinase-activated receptor 1
antagonist
Human
Absorption

After oral administration, vorapaxar is rapidly absorbed and peak concentrations occur at a median tmax of 1 hour under faster conditions. Vorapaxar may be taken with or without food as ingestion with a high-fat meal did not result in meaningful changes in AUC. The mean absolute bioavailability is 100%.

Volume of distribution

424 L

Protein binding

Vorapaxar is extensively bound (>99%) to human plasma proteins, such as human serum albumin.

Metabolism

Vorapaxar is metabolized to its major circulating metabolite, M20, and its predominant metabolite excreted into feces, M19, by CYP3A4 and CYP 2J2.

Route of elimination

Vorapaxar is primarily eliminated as its metabolite M19 through the feces (91.5%), and partially eliminated in the urine (8.5%).

Half life

Vorapaxar has an effective half life of 3-4 days and an apparent terminal half life of 8 days.

Clearance
Not Available
Toxicity

There is an increased risk of bleeding and intracranial hemorrhage (ICH), which is why the use of vorapaxar is contraindicated in patients with a history of stroke, trans-ischemic attack (TIA), ICH, or active pathological bleeding such as peptic ulcer. Animal studies have suggested that there is a low probability of embryo/fetal toxicities, however there are no adequate and well-controlled studies describing use in pregnant women. Vorapaxar should also be avoided during breastfeeding as it is unknown whether vorapaxar or its metabolites are excreted in human milk, however it has been shown to be actively secreted in the milk of rats.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbciximabThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Abciximab.Approved
AcenocoumarolThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Acenocoumarol.Approved
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Acetylsalicylic acid.Approved, Vet Approved
AloxiprinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Aloxiprin.Experimental
AlprostadilAlprostadil may increase the anticoagulant activities of Vorapaxar.Approved, Investigational
AlteplaseVorapaxar may increase the anticoagulant activities of Alteplase.Approved
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Aminosalicylic Acid.Approved
AmiodaroneThe serum concentration of Vorapaxar can be increased when it is combined with Amiodarone.Approved, Investigational
AnagrelideVorapaxar may increase the anticoagulant activities of Anagrelide.Approved
AncrodThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Ancrod.Investigational
AndrographolideAndrographolide may increase the anticoagulant activities of Vorapaxar.Investigational
AnistreplaseVorapaxar may increase the anticoagulant activities of Anistreplase.Approved
Antithrombin III humanThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Antithrombin III human.Approved
ApixabanThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Apixaban.Approved
AprotininThe therapeutic efficacy of Vorapaxar can be decreased when used in combination with Aprotinin.Approved, Withdrawn
ArdeparinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Ardeparin.Approved, Investigational, Withdrawn
ArgatrobanThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Argatroban.Approved, Investigational
AstaxanthinVorapaxar may increase the anticoagulant activities of Astaxanthin.Investigational
AtazanavirThe serum concentration of Vorapaxar can be increased when it is combined with Atazanavir.Approved, Investigational
AzelastineAzelastine may increase the anticoagulant activities of Vorapaxar.Approved
BalsalazideThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Balsalazide.Approved, Investigational
BatroxobinVorapaxar may increase the anticoagulant activities of Batroxobin.Experimental
BecaplerminThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Becaplermin.Approved, Investigational
BemiparinVorapaxar may increase the anticoagulant activities of Bemiparin.Approved, Investigational
BeraprostVorapaxar may increase the anticoagulant activities of Beraprost.Investigational
BivalirudinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Vorapaxar can be increased when it is combined with Boceprevir.Approved, Withdrawn
BrinaseVorapaxar may increase the anticoagulant activities of Brinase.Experimental
BuflomedilBuflomedil may increase the anticoagulant activities of Vorapaxar.Experimental
ButylphthalideButylphthalide may increase the anticoagulant activities of Vorapaxar.Investigational
CangrelorVorapaxar may increase the anticoagulant activities of Cangrelor.Approved
CaplacizumabVorapaxar may increase the anticoagulant activities of Caplacizumab.Investigational
CarbamazepineThe serum concentration of Vorapaxar can be decreased when it is combined with Carbamazepine.Approved, Investigational
Carbaspirin calciumThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Carbaspirin calcium.Experimental, Investigational
CeritinibThe serum concentration of Vorapaxar can be increased when it is combined with Ceritinib.Approved
CertoparinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Certoparin.Approved, Investigational
CilostazolVorapaxar may increase the anticoagulant activities of Cilostazol.Approved
Citric AcidThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Citric Acid.Approved, Nutraceutical, Vet Approved
ClarithromycinThe serum concentration of Vorapaxar can be increased when it is combined with Clarithromycin.Approved
ClopidogrelClopidogrel may increase the anticoagulant activities of Vorapaxar.Approved
CloricromenVorapaxar may increase the anticoagulant activities of Cloricromen.Experimental
ClorindioneVorapaxar may increase the anticoagulant activities of Clorindione.Experimental
CobicistatThe serum concentration of Vorapaxar can be increased when it is combined with Cobicistat.Approved
Collagenase clostridium histolyticumThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Collagenase clostridium histolyticum.Approved, Investigational
Dabigatran etexilateVorapaxar may increase the anticoagulant activities of Dabigatran etexilate.Approved
DalteparinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Dalteparin.Approved
DanaparoidThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Danaparoid.Approved, Withdrawn
DarexabanThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Darexaban.Investigational
DarunavirThe serum concentration of Vorapaxar can be increased when it is combined with Darunavir.Approved
DasatinibDasatinib may increase the anticoagulant activities of Vorapaxar.Approved, Investigational
DefibrotideVorapaxar may increase the anticoagulant activities of Defibrotide.Approved, Investigational
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Deoxycholic Acid.Approved
DersalazineThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Dersalazine.Investigational
DesirudinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Desirudin.Approved
DesmoteplaseVorapaxar may increase the anticoagulant activities of Desmoteplase.Investigational
DextranThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Dextran.Approved, Vet Approved
Dextran 40The risk or severity of adverse effects can be increased when Vorapaxar is combined with Dextran 40.Approved
Dextran 70The risk or severity of adverse effects can be increased when Vorapaxar is combined with Dextran 70.Approved
Dextran 75The risk or severity of adverse effects can be increased when Vorapaxar is combined with Dextran 75.Approved
DicoumarolThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Dicoumarol.Approved
DiflunisalThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Diflunisal.Approved
DiphenadioneVorapaxar may increase the anticoagulant activities of Diphenadione.Experimental
DipyridamoleDipyridamole may increase the anticoagulant activities of Vorapaxar.Approved
DitazoleVorapaxar may increase the anticoagulant activities of Ditazole.Approved, Withdrawn
Drotrecogin alfaVorapaxar may increase the anticoagulant activities of Drotrecogin alfa.Approved, Investigational, Withdrawn
Edetic AcidThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Edetic Acid.Approved, Vet Approved
EdoxabanThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Edoxaban.Approved
EnoxaparinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Enoxaparin.Approved
EnzalutamideThe serum concentration of Vorapaxar can be decreased when it is combined with Enzalutamide.Approved
EpinastineEpinastine may increase the anticoagulant activities of Vorapaxar.Approved, Investigational
EplivanserinVorapaxar may increase the anticoagulant activities of Eplivanserin.Investigational
eplivanserineVorapaxar may increase the anticoagulant activities of eplivanserine.Investigational
EpoprostenolVorapaxar may increase the anticoagulant activities of Epoprostenol.Approved
EptifibatideEptifibatide may increase the anticoagulant activities of Vorapaxar.Approved, Investigational
Ethyl biscoumacetateThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Ethyl biscoumacetate.Withdrawn
Ferulic acidThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Ferulic acid.Experimental
FibrinolysinVorapaxar may increase the anticoagulant activities of Fibrinolysin.Investigational
FluindioneThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Fluindione.Investigational
FondaparinuxThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Fondaparinux.Investigational
Fondaparinux sodiumThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Fondaparinux sodium.Approved, Investigational
FosphenytoinThe serum concentration of Vorapaxar can be decreased when it is combined with Fosphenytoin.Approved
GabexateThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Gabexate.Investigational
GlucosamineGlucosamine may increase the antiplatelet activities of Vorapaxar.Approved
GuacetisalThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Guacetisal.Experimental
Hemoglobin crosfumarilThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Hemoglobin crosfumaril.Experimental
HeparinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Heparin.Approved, Investigational
HigenamineVorapaxar may increase the anticoagulant activities of Higenamine.Investigational
HydroxytyrosolHydroxytyrosol may increase the anticoagulant activities of Vorapaxar.Investigational
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Ibritumomab tiuxetan.Approved
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Vorapaxar.Approved
IbudilastIbudilast may increase the anticoagulant activities of Vorapaxar.Approved, Investigational
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Vorapaxar.Approved, Nutraceutical
IdelalisibThe serum concentration of Vorapaxar can be increased when it is combined with Idelalisib.Approved
IdraparinuxThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Idraparinux.Investigational
IfenprodilIfenprodil may increase the anticoagulant activities of Vorapaxar.Approved, Investigational, Withdrawn
IfetrobanIfetroban may increase the anticoagulant activities of Vorapaxar.Investigational
IloprostVorapaxar may increase the anticoagulant activities of Iloprost.Approved, Investigational
IndinavirThe serum concentration of Vorapaxar can be increased when it is combined with Indinavir.Approved
IndobufenVorapaxar may increase the anticoagulant activities of Indobufen.Investigational
ItraconazoleThe serum concentration of Vorapaxar can be increased when it is combined with Itraconazole.Approved, Investigational
KetanserinKetanserin may increase the anticoagulant activities of Vorapaxar.Investigational
KetoconazoleThe serum concentration of Vorapaxar can be increased when it is combined with Ketoconazole.Approved, Investigational
LepirudinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Lepirudin.Approved
LetaxabanThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Letaxaban.Investigational
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Vorapaxar.Approved, Investigational
LinsidomineLinsidomine may increase the anticoagulant activities of Vorapaxar.Experimental
LopinavirThe serum concentration of Vorapaxar can be increased when it is combined with Lopinavir.Approved
LumacaftorThe serum concentration of Vorapaxar can be decreased when it is combined with Lumacaftor.Approved
MelagatranThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Melagatran.Experimental
MesalazineThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Mesalazine.Approved
Methyl salicylateThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Methyl salicylate.Approved, Vet Approved
MilrinoneMilrinone may increase the anticoagulant activities of Vorapaxar.Approved
MitotaneThe serum concentration of Vorapaxar can be decreased when it is combined with Mitotane.Approved
NadroparinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Nadroparin.Approved
NafamostatThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Nafamostat.Approved, Investigational
NaftopidilNaftopidil may increase the anticoagulant activities of Vorapaxar.Investigational
NefazodoneThe serum concentration of Vorapaxar can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Vorapaxar can be increased when it is combined with Nelfinavir.Approved
NevirapineThe serum concentration of Vorapaxar can be decreased when it is combined with Nevirapine.Approved
NimesulideNimesulide may increase the anticoagulant activities of Vorapaxar.Approved, Investigational, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Nitroaspirin.Investigational
ObinutuzumabThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Obinutuzumab.Approved
OlsalazineThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Olsalazine.Approved
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Vorapaxar.Approved, Nutraceutical
OtamixabanThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Otamixaban.Investigational
OzagrelVorapaxar may increase the anticoagulant activities of Ozagrel.Investigational
ParnaparinVorapaxar may increase the anticoagulant activities of Parnaparin.Approved, Investigational
Pentaerythritol TetranitrateThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Pentaerythritol Tetranitrate.Approved
PentobarbitalThe serum concentration of Vorapaxar can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Vorapaxar.Approved
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Vorapaxar.Approved, Investigational
PhenindioneThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Phenindione.Approved, Investigational
PhenobarbitalThe serum concentration of Vorapaxar can be decreased when it is combined with Phenobarbital.Approved
PhenprocoumonThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Phenprocoumon.Approved, Investigational
PhenytoinThe serum concentration of Vorapaxar can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PicotamideVorapaxar may increase the anticoagulant activities of Picotamide.Experimental
PosaconazoleThe serum concentration of Vorapaxar can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrasugrelPrasugrel may increase the anticoagulant activities of Vorapaxar.Approved
PrimidoneThe serum concentration of Vorapaxar can be decreased when it is combined with Primidone.Approved, Vet Approved
Protein CThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Protein C.Approved
Protein S humanThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Protein S human.Approved
ProtocatechualdehydeThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Protocatechualdehyde.Approved
RamatrobanRamatroban may increase the anticoagulant activities of Vorapaxar.Investigational
RelcovaptanRelcovaptan may increase the anticoagulant activities of Vorapaxar.Investigational
ResveratrolResveratrol may increase the anticoagulant activities of Vorapaxar.Approved, Experimental, Investigational
ReteplaseVorapaxar may increase the anticoagulant activities of Reteplase.Approved
ReviparinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Reviparin.Approved, Investigational
RidogrelRidogrel may increase the anticoagulant activities of Vorapaxar.Approved
RifabutinThe serum concentration of Vorapaxar can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Vorapaxar can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Vorapaxar can be decreased when it is combined with Rifapentine.Approved
RivaroxabanVorapaxar may increase the anticoagulant activities of Rivaroxaban.Approved
RosiglitazoneVorapaxar may increase the anticoagulant activities of Rosiglitazone.Approved, Investigational
Salicylic acidThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Salicylic acid.Approved, Vet Approved
SaquinavirThe serum concentration of Vorapaxar can be increased when it is combined with Saquinavir.Approved, Investigational
SarpogrelateVorapaxar may increase the anticoagulant activities of Sarpogrelate.Investigational
SaruplaseVorapaxar may increase the anticoagulant activities of Saruplase.Experimental
SelexipagVorapaxar may increase the anticoagulant activities of Selexipag.Approved
SevofluraneSevoflurane may increase the anticoagulant activities of Vorapaxar.Approved, Vet Approved
SRT501SRT501 may increase the anticoagulant activities of Vorapaxar.Investigational
St. John's WortThe serum concentration of Vorapaxar can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Vorapaxar can be increased when it is combined with Stiripentol.Approved
StreptokinaseVorapaxar may increase the anticoagulant activities of Streptokinase.Approved, Investigational
SulodexideThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Sulodexide.Approved, Investigational
TelaprevirThe serum concentration of Vorapaxar can be increased when it is combined with Telaprevir.Approved, Withdrawn
TelithromycinThe serum concentration of Vorapaxar can be increased when it is combined with Telithromycin.Approved
TenecteplaseVorapaxar may increase the anticoagulant activities of Tenecteplase.Approved
TesmilifeneTesmilifene may increase the anticoagulant activities of Vorapaxar.Investigational
TicagrelorVorapaxar may increase the anticoagulant activities of Ticagrelor.Approved
TiclopidineTiclopidine may increase the anticoagulant activities of Vorapaxar.Approved
TinzaparinVorapaxar may increase the anticoagulant activities of Tinzaparin.Approved
TioclomarolVorapaxar may increase the anticoagulant activities of Tioclomarol.Experimental
TipranavirTipranavir may increase the antiplatelet activities of Vorapaxar.Approved, Investigational
TirofibanTirofiban may increase the anticoagulant activities of Vorapaxar.Approved
TositumomabThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Tositumomab.Approved, Investigational
TranilastTranilast may increase the anticoagulant activities of Vorapaxar.Approved, Investigational
TrapidilTrapidil may increase the anticoagulant activities of Vorapaxar.Approved
TreprostinilVorapaxar may increase the anticoagulant activities of Treprostinil.Approved, Investigational
TriflusalVorapaxar may increase the anticoagulant activities of Triflusal.Approved, Investigational
Trolamine salicylateThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Trolamine salicylate.Approved
TroxerutinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Troxerutin.Investigational
UrokinaseVorapaxar may increase the anticoagulant activities of Urokinase.Approved, Investigational, Withdrawn
Vitamin EVitamin E may increase the antiplatelet activities of Vorapaxar.Approved, Nutraceutical, Vet Approved
VoriconazoleThe serum concentration of Vorapaxar can be increased when it is combined with Voriconazole.Approved, Investigational
WarfarinThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Warfarin.Approved
XimelagatranThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Ximelagatran.Approved, Investigational, Withdrawn
Food Interactions
Not Available

References

General References
  1. Ghosal A, Lu X, Penner N, Gao L, Ramanathan R, Chowdhury SK, Kishnani NS, Alton KB: Identification of human liver cytochrome P450 enzymes involved in the metabolism of SCH 530348 (Vorapaxar), a potent oral thrombin protease-activated receptor 1 antagonist. Drug Metab Dispos. 2011 Jan;39(1):30-8. doi: 10.1124/dmd.110.035493. Epub 2010 Oct 6. [PubMed:20926621]
  2. Lhermusier T, Baker NC, Waksman R: Overview of the 2014 Food and Drug Administration Cardiovascular and Renal Drugs Advisory Committee meeting regarding cangrelor. Am J Cardiol. 2015 Apr 15;115(8):1154-61. doi: 10.1016/j.amjcard.2015.01.551. Epub 2015 Feb 3. [PubMed:25728646]
  3. Tricoci P, Huang Z, Held C, Moliterno DJ, Armstrong PW, Van de Werf F, White HD, Aylward PE, Wallentin L, Chen E, Lokhnygina Y, Pei J, Leonardi S, Rorick TL, Kilian AM, Jennings LH, Ambrosio G, Bode C, Cequier A, Cornel JH, Diaz R, Erkan A, Huber K, Hudson MP, Jiang L, Jukema JW, Lewis BS, Lincoff AM, Montalescot G, Nicolau JC, Ogawa H, Pfisterer M, Prieto JC, Ruzyllo W, Sinnaeve PR, Storey RF, Valgimigli M, Whellan DJ, Widimsky P, Strony J, Harrington RA, Mahaffey KW: Thrombin-receptor antagonist vorapaxar in acute coronary syndromes. N Engl J Med. 2012 Jan 5;366(1):20-33. doi: 10.1056/NEJMoa1109719. Epub 2011 Nov 13. [PubMed:22077816]
  4. Cheng JW, Colucci V, Howard PA, Nappi JM, Spinler SA: Vorapaxar in atherosclerotic disease management. Ann Pharmacother. 2015 May;49(5):599-606. doi: 10.1177/1060028015571410. Epub 2015 Feb 13. [PubMed:25680760]
External Links
KEGG Drug
D09766
PubChem Compound
10077130
PubChem Substance
310264983
ChemSpider
8252668
BindingDB
50261110
ChEBI
82702
ChEMBL
CHEMBL493982
HET
VPX
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Vorapaxar
ATC Codes
B01AC26 — Vorapaxar
AHFS Codes
  • 20:12.18 — Platelet Aggregation Inhibitors
PDB Entries
3vw7
FDA label
Download (651 KB)
MSDS
Download (49.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAcute Coronary Syndromes (ACS)1
1, 2RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
2CompletedPreventionArterial Obstructive Diseases / Coronary Heart Disease (CHD)1
2CompletedTreatmentAtherosclerosis / Myocardial Infarction (MI) / Myocardial Ischemia1
2CompletedTreatmentCerebral Infarctions1
2CompletedTreatmentFistula / Fistula Function Maturation1
3CompletedPreventionAtherosclerosis / Cerebrovascular Accidents / Myocardial Infarction (MI) / Peripheral Arterial Disease (PAD) / Transient ischemia attacks1
3CompletedPreventionAtherosclerosis / Cerebrovascular Accidents / Myocardial Infarction (MI) / Transient ischemia attacks1
3TerminatedPreventionAtherosclerosis / Myocardial Infarction (MI) / Myocardial Ischemia1
4CompletedTreatmentHealthy Volunteers1
4Not Yet RecruitingHealth Services ResearchCoronary Artery Disease1
4Not Yet RecruitingOtherPeripheral Artery Disease (PAD)1
4RecruitingHealth Services ResearchCoronary Artery Disease / Myocardial Infarction (MI) / Peripheral Vascular Disease (PVD)1
4RecruitingTreatmentDiabetes Mellitus (DM) / Myocardial Infarction (MI) / Peripheral Arterial Disease (PAD)1
4RecruitingTreatmentMyocardial Infarction (MI)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral2.5 mg
Tablet, film coatedOral2.08 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7304078No2004-04-062024-04-06Us
US7235567No2001-06-132021-06-13Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP5.39ChEMBL
Predicted Properties
PropertyValueSource
Water Solubility0.000787 mg/mLALOGPS
logP5.2ALOGPS
logP5.82ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)8ChemAxon
pKa (Strongest Basic)4.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area81.01 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity135.31 m3·mol-1ChemAxon
Polarizability54.8 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as naphthofurans. These are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Naphthofurans
Sub Class
Not Available
Direct Parent
Naphthofurans
Alternative Parents
Phenylpyridines / Fluorobenzenes / Aryl fluorides / Gamma butyrolactones / Tetrahydrofurans / Carbamate esters / Heteroaromatic compounds / Carboxylic acid esters / Organic carbonic acids and derivatives / Oxacyclic compounds
show 8 more
Substituents
Naphthofuran / 3-phenylpyridine / Fluorobenzene / Halobenzene / Aryl fluoride / Aryl halide / Monocyclic benzene moiety / Gamma butyrolactone / Pyridine / Benzenoid
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, carbamate ester, pyridines, lactone, naphthofuran (CHEBI:82702)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Thrombin receptor activity
Specific Function
High affinity receptor for activated thrombin coupled to G proteins that stimulate phosphoinositide hydrolysis. May play a role in platelets activation and in vascular development.
Gene Name
F2R
Uniprot ID
P25116
Uniprot Name
Proteinase-activated receptor 1
Molecular Weight
47439.83 Da
References
  1. Bonaca MP, Morrow DA: SCH 530348: a novel oral thrombin receptor antagonist. Future Cardiol. 2009 Sep;5(5):435-42. doi: 10.2217/fca.09.27. [PubMed:19715408]

Drug created on February 09, 2015 15:24 / Updated on January 15, 2018 08:58