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Compound Detail

CHEMBL493982

VORAPAXAR
💊 Approved Drug
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💊 Approved Drug
CCOC(=O)N[C@@H]1CC[C@@H]2[C@@H](C1)C[C@H]1C(=O)O[C@H](C)[C@H]1[C@H]2/C=C/c1ccc(-c2cccc(F)c2)cn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL493982
Name VORAPAXAR
Phase Approved
Structure Type MOL
InChI Key ZBGXUVOIWDMMJE-QHNZEKIYSA-N
Therapeutic ✓ Yes

Known Names

Vorapaxar
4
Targets
17
Activities
2
Assay Types
19
PK Parameters
20
Publications
1
Known Names
3
Indications

Molecular Properties

492.6
MW (Da)
5.63
ALogP
5
HBA
1
HBD
77.5
PSA (Ų)
0.55
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2014
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning First in Class
USAN Stem -paxar
USAN Year 2009

Extended Properties

Molecular Formula C29H33FN2O4
MW 492.59
Aromatic Rings 2
Heavy Atoms 36
NP-Likeness -0.08

Indications

Thrombosis Cerebral Infarction HIV Infections

ATC Classification

B01AC26
vorapaxar
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: ANTITHROMBOTIC AGENTS

Activity Summary

IC50 12 meas. best 8.96
Ki 5 meas. best 8.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Proteinase-activated receptor 1
CHEMBL3974
 IC50 8.96 7.5578 1.1 9
Proteinase-activated receptor 1
CHEMBL3974
 Ki 8.96 8.222 1.1 5
Platelet
CHEMBL4296519
 IC50 7.33 7.33 47.0 1
G-protein coupled receptor 183
CHEMBL3259470
 IC50 5.32 5.32 4765.2 1
G-protein coupled receptor 35
CHEMBL1293267
 IC50 5.12 5.12 7574.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2610.73 ng.hr.mL-1 Rattus norvegicus
AUC 4925.9 ng.hr.mL-1 Macaca mulatta
AUC 98.52 ng.hr.mL-1 Macaca fascicularis
AUC 3064.0 ng.hr.mL-1 Rattus norvegicus
AUC 3064.0 ng.hr.mL-1 Rattus norvegicus
AUC 3500.0 ng.hr.mL-1 Rattus norvegicus
Cmax 670.0 nM Rattus norvegicus
Cmax 1300.0 nM Macaca mulatta
Cmax 18.0 nM Macaca fascicularis
Cmax 1977.3 nM Rattus norvegicus
Cmax 893.24 nM Rattus norvegicus
F 33.0 % Rattus norvegicus
F 86.0 % Macaca mulatta
F 94.0 % Rattus norvegicus
T1/2 5.1 hr Rattus norvegicus
T1/2 13.0 hr Macaca mulatta
T1/2 4.0 hr Rattus norvegicus
Tmax 3.0 hr Rattus norvegicus
Tmax 1.0 hr Macaca mulatta

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Proteinase-activated receptor 1 IC50 = 1.1 nM 8.96 Displacement of [3H]haTRAP from PAR1 in human platelet membranes after 60 mins b... 24900604
Proteinase-activated receptor 1 Ki = 1.1 nM 8.96 Antagonist activity at human PAR1 in HCASMC assessed as inhibition of thrombin-i... 18447380
Proteinase-activated receptor 1 IC50 = 1.5 nM 8.82 Antagonist activity at PAR1 in washed human platelets assessed as inhibition of ... 24900604
Proteinase-activated receptor 1 Ki = 8.0 nM 8.1 Displacement of high affinity TRAP form human platelet PAR1 20888225
Proteinase-activated receptor 1 Ki = 8.1 nM 8.09 Displacement of [3H]haTRAP from PAR1 in human platelets 18447380
Proteinase-activated receptor 1 Ki = 8.5 nM 8.07 Displacement of [3H]haTRAP from PAR-1 isolated from human platelets by liquid sc... 24900795
Proteinase-activated receptor 1 Ki = 13.0 nM 7.89 Antagonist activity at human PAR1 in HCASMC assessed as inhibition of thrombin-i... 18447380
Proteinase-activated receptor 1 IC50 = 25.0 nM 7.6 Antagonist activity at PAR1 in human platelets assessed as inhibition of haTRAP-... 18447380
Proteinase-activated receptor 1 IC50 = 31.0 nM 7.51 Antagonist activity at PAR1 in human platelet-rich plasma assessed as reduction ... 28745507
Platelet IC50 = 47.0 nM 7.33 Inhibition of thrombin-induced human platelet aggregation 38889609
Proteinase-activated receptor 1 IC50 = 47.0 nM 7.33 Antagonist activity at PAR1 in human platelets assessed as inhibition of thrombi... 18447380
Proteinase-activated receptor 1 IC50 = 64.0 nM 7.19 Antagonist activity at human PAR1 expressed in HEK293 cells co-expressing Galpha... 28745507
Proteinase-activated receptor 1 IC50 = 81.0 nM 7.09 Antagonist activity at PAR1 in human platelet-rich plasma assessed as reduction ... 28745507
Proteinase-activated receptor 1 IC50 = 120.0 nM 6.92 Antagonist activity at PAR1 in human platelet rich plasma assessed as inhibition... 24900604
Proteinase-activated receptor 1 IC50 = 250.0 nM 6.6 Antagonist activity at human PAR1 expressed in KNRK cells assessed as inhibition... 32122739
G-protein coupled receptor 183 IC50 = 4765.24 nM 5.32 GPCR PRESTO-Tango dose-response in antagonist mode with target: GPR183 -
G-protein coupled receptor 35 IC50 = 7574.0 nM 5.12 GPCR PRESTO-Tango dose-response in antagonist mode with target: GPR35 -

Literature References

PubMed DOI Target Context # Activities
20926621 10.1124/dmd.110.035493 Liver microsome 18
18447380 10.1021/jm800180e Proteinase-activated receptor 1 9
- 10.6019/CHEMBL5058564 Fibroblast 8
- 10.6019/CHEMBL5058564 HEK-293T 7
18447380 10.1021/jm800180e Rattus norvegicus 6
18447380 10.1021/jm800180e Rhesus monkey 6
20926621 10.1124/dmd.110.035493 ADMET 6
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5
32122739 10.1016/j.bmcl.2020.127046 ADMET 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 5
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 Apelin receptor 5
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 5
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 5
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5

Data from ChEMBL 36 via Core Engine