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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H33FN2O4
Molecular Weight 492.5817
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of VORAPAXAR

SMILES

[H][C@@]12C[C@]3([H])C[C@@]([H])(CC[C@@]3([H])[C@]([H])(\C=C\C4=CC=C(C=N4)C5=CC(F)=CC=C5)[C@]1([H])[C@@H](C)OC2=O)NC(=O)OCC

InChI

InChIKey=ZBGXUVOIWDMMJE-QHNZEKIYSA-N
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

HIDE SMILES / InChI

Molecular Formula C29H33FN2O4
Molecular Weight 492.5817
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Vorapaxar is a tricyclic himbacine-derived oral thrombin receptor antagonist that acts by reversible inhibition of the protease-activated receptor-1 (PAR-1). PAR-1 is expressed on platelets and its inhibition prevents platelets from aggregation. Vorapaxar is approved by FDA and is indicated for the reduction of recurring thrombotic cardiovascular events in patients with a history of myocardial infarction or with peripheral arterial disease. Vorapaxar at the same time may cause bleeding complications including intracranial haemorrhage (ICH), when compared to standard therapy alone. That is why Vorapaxar is contraindicated in patients with prior stroke, transient ischemic attack and ICH.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
13.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
ZONTIVITY
Preventing
ZONTIVITY

Cmax

ValueDoseCo-administeredAnalytePopulation
262 ng/mL
40 mg single, oral
VORAPAXAR plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
18400 ng × h/mL
40 mg single, oral
VORAPAXAR plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
240 h
40 mg single, oral
VORAPAXAR plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
One tablet of ZONTIVITY orally once daily (Tablets: 2.08 mg vorapaxar)
Route of Administration: Oral
In Vitro Use Guide
In human platelet-rich plasma,vorapaxar inhibited thrombin and TRAP-induced platelet aggregation with an IC50 of 47 and 25nM, respectively, without affecting aggregation induced by other reagents, such as ADP, TXA2 mimetic U46619 or collagen.
Substance Class Chemical
Record UNII
ZCE93644N2
Record Status Validated (UNII)
Record Version