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Identification
NameVorapaxar
Accession NumberDB09030
TypeSmall Molecule
GroupsApproved
DescriptionVorapaxar 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 Identifiers
  • MFCD16038876
  • SCH 530348
  • SCH-530348
  • SCH530348
  • ZCE93644N2
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ZontivityTablet, film coated2.08 mg/1OralMerck Sharp & Dohme Corp.2014-05-08Not applicableUs
ZontivityTablet2.5 mgOralAralez Pharmaceuticals Trading DacNot applicableNot applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Vorapaxar Sulfate
Thumb
  • InChI Key: NQRYCIGCIAWEIC-CKLVGUEFSA-N
  • Monoisotopic Mass: 590.209815432
  • Average Mass: 590.66
DBSALT001104
Categories
UNIIZCE93644N2
CAS number618385-01-6
WeightAverage: 492.5817
Monoisotopic: 492.242435759
Chemical FormulaC29H33FN2O4
InChI KeyZBGXUVOIWDMMJE-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])[C@]1([H])[C@]2([H])[C@@]([H])(C)OC(=O)[C@]2([H])C[C@]2([H])C[C@@]([H])(CC[C@@]12[H])N=C(O)OCC)C1=NC=C(C=C1)C1=CC(F)=CC=C1
Pharmacology
IndicationVorapaxar 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
PharmacodynamicsNot Available
Mechanism of actionVorapaxar 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Proteinase-activated receptor 1Proteinyes
antagonist
HumanP25116 details
Related Articles
AbsorptionAfter 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 bindingVorapaxar 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.

SubstrateEnzymesProduct
Vorapaxar
amine metabolite (M19)Details
Vorapaxar
monohydroxy-vorapaxar (M20)Details
Route of eliminationVorapaxar is primarily eliminated as its metabolite M19 through the feces (91.5%), and partially eliminated in the urine (8.5%).
Half lifeVorapaxar has an effective half life of 3-4 days and an apparent terminal half life of 8 days.
ClearanceNot Available
ToxicityThere 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 organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot 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
AlprostadilAlprostadil may increase the anticoagulant activities of Vorapaxar.Approved, Investigational
AlteplaseVorapaxar may increase the anticoagulant activities of Alteplase.Approved
ALX-0081Vorapaxar may increase the anticoagulant activities of ALX-0081.Investigational
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
AnagrelideAnagrelide may increase the anticoagulant activities of Vorapaxar.Approved
AncrodThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Ancrod.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, 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
BeraprostBeraprost may increase the anticoagulant activities of Vorapaxar.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
ButylphthalideButylphthalide may increase the anticoagulant activities of Vorapaxar.Investigational
CangrelorCangrelor may increase the anticoagulant activities of Vorapaxar.Approved
CarbamazepineThe serum concentration of Vorapaxar can be decreased when it is combined with Carbamazepine.Approved, 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
CilostazolCilostazol may increase the anticoagulant activities of Vorapaxar.Approved
Citric AcidThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Citric Acid.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, Nutraceutical
CobicistatThe serum concentration of Vorapaxar can be increased when it is combined with Cobicistat.Approved
CollagenaseThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Collagenase.Approved
Dabigatran etexilateThe risk or severity of adverse effects can be increased when Vorapaxar is combined with 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
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
DefibrotideDefibrotide may increase the anticoagulant activities of Vorapaxar.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
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
eplivanserineVorapaxar may increase the anticoagulant activities of eplivanserine.Investigational
EpoprostenolEpoprostenol may increase the antiplatelet activities of Vorapaxar.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
FibrinolysinVorapaxar may increase the anticoagulant activities of Fibrinolysin.Approved
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
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
HirulogThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Hirulog.Experimental
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, Withdrawn
IloprostIloprost may increase the antiplatelet activities of Vorapaxar.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
Kct 0809Vorapaxar may increase the anticoagulant activities of Kct 0809.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
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Vorapaxar.Approved
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
MesalazineThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Mesalazine.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.Investigational
NaftopidilNaftopidil may increase the anticoagulant activities of Vorapaxar.Investigational
NCX 4016The risk or severity of adverse effects can be increased when Vorapaxar is combined with NCX 4016.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, 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
OtamixabanThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Otamixaban.Investigational
ParnaparinVorapaxar may increase the anticoagulant activities of Parnaparin.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 Vorapaxar is combined with Pentosan Polysulfate.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
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
PhenytoinThe serum concentration of Vorapaxar can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PlasminVorapaxar may increase the anticoagulant activities of Plasmin.Investigational
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
ResveratrolResveratrol may increase the anticoagulant activities of Vorapaxar.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
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
RitonavirThe serum concentration of Vorapaxar can be increased when it is combined with Ritonavir.Approved, Investigational
RivaroxabanThe risk or severity of adverse effects can be increased when Vorapaxar is combined with 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
SCH-530348SCH-530348 may increase the anticoagulant activities of Vorapaxar.Investigational
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.Nutraceutical
StreptokinaseVorapaxar may increase the anticoagulant activities of Streptokinase.Approved
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
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
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
TranilastTranilast may increase the anticoagulant activities of Vorapaxar.Approved, Investigational
TrapidilTrapidil may increase the anticoagulant activities of Vorapaxar.Approved
TreprostinilTreprostinil may increase the antiplatelet activities of Vorapaxar.Approved, Investigational
TriflusalTriflusal may increase the anticoagulant activities of Vorapaxar.Approved
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
Ym150The risk or severity of adverse effects can be increased when Vorapaxar is combined with Ym150.Investigational
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesB01AC26
AHFS Codes
  • 20:12.18
PDB EntriesNot Available
FDA labelDownload (651 KB)
MSDSDownload (49.5 KB)
ADMET
Predicted ADMET featuresNot Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
TabletOral2.5 mg
Tablet, film coatedOral2.08 mg/1
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7235567 No2001-06-132021-06-13Us
US7304078 No2004-04-062024-04-06Us
Properties
StateSolid
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthofurans
Sub ClassNot Available
Direct ParentNaphthofurans
Alternative Parents
Substituents
  • Naphthofuran
  • 3-phenylpyridine
  • Halobenzene
  • Fluorobenzene
  • Cyclohexylamine
  • Benzenoid
  • Pyridine
  • Gamma butyrolactone
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Oxolane
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

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
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 ]
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Drug created on February 09, 2015 15:24 / Updated on December 05, 2016 02:44