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Vorapaxar

PubChem CID
10077130
Structure
Vorapaxar_small.png
Vorapaxar_3D_Structure.png
Molecular Formula
Synonyms
  • Vorapaxar
  • 618385-01-6
  • SCH530348
  • SCH-530348
  • Sch 530348
Molecular Weight
492.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-10-25
  • Modify:
    2025-01-04
Description
Vorapaxar is a carbamate ester that is the ethyl ester of [(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethynyl}-1-methyl-3-oxododecahydronaphtho[2,3-c]furan-6-yl]carbamic acid. A protease-activated receptor-1 antagonist used (as its sulfate salt) for the reduction of thrombotic cardiovascular events in patients with a history of myocardial infarction (MI) or with peripheral arterial disease. It has been shown to reduce the rate of a combined endpoint of cardiovascular death, MI, stroke and urgent coronary revascularisation. It has a role as a protease-activated receptor-1 antagonist, a platelet aggregation inhibitor and a cardiovascular drug. It is a member of pyridines, a carbamate ester, an organofluorine compound, a naphthofuran and a lactone. It is a conjugate base of a vorapaxar(1+).
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.
Vorapaxar is a Protease-activated Receptor-1 Antagonist. The mechanism of action of vorapaxar is as a Protease-activated Receptor-1 Antagonist.
See also: Vorapaxar Sulfate (active moiety of).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Vorapaxar.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

ethyl N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl]-1-methyl-3-oxo-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-1H-benzo[f][2]benzofuran-6-yl]carbamate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

ZBGXUVOIWDMMJE-QHNZEKIYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCOC(=O)N[C@@H]1CC[C@@H]2[C@@H](C1)C[C@@H]3[C@H]([C@H]2/C=C/C4=NC=C(C=C4)C5=CC(=CC=C5)F)[C@H](OC3=O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C29H33FN2O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 KEGG ID

2.3.9 Metabolomics Workbench ID

2.3.10 NCI Thesaurus Code

2.3.11 Nikkaji Number

2.3.12 PharmGKB ID

2.3.13 Pharos Ligand ID

2.3.14 Wikidata

2.3.15 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • SCH 530348
  • SCH-530348
  • SCH530348
  • vorapaxar
  • Zontivity

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
492.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
5.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
492.24243570 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
492.24243570 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
77.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
36
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
821
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
7
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 LogP

5.39
ChEMBL

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Blood and blood forming organs -> Antithrombotic agents
S92 | FLUOROPHARMA | List of ~340 ATC classified fluoro-pharmaceuticals | DOI:10.5281/zenodo.5979646
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
3.3.1.1 Human Drugs
Human drugs -> Antithrombotic agents -> Human pharmacotherapeutic group -> EMA Drug Category
Paediatric drug

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug 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.
Zontivityis indicated for the reduction of atherothrombotic events in adult patients with- a history of myocardial infarction (MI), ,co-administered with acetylsalicylic acid (ASA) and, where appropriate, clopidogrel; or- symptomatic peripheral arterial disease(PAD), co-administered with acetylsalicylic acid (ASA) or, where appropriate, clopidogrel.

6.2 LiverTox Summary

Vorapaxar is an inhibitor of platelet aggregation that is used to decrease the risk of further cardiovascular thrombotic events in patients with a history of myocardial infarction or peripheral vascular disease. Vorapaxar therapy is associated with a low rate of serum aminotransferase elevations, but has not been linked to instances of clinically apparent acute liver injury.

6.3 Drug Classes

Antithrombotic Agents

6.4 Drug Labels

Drug and label

6.5 Clinical Trials

6.5.1 ClinicalTrials.gov

6.5.2 EU Clinical Trials Register

6.6 EMA Drug Information

1 of 2
Medicine
Category
Human drugs
Therapeutic area
Myocardial Infarction
Active Substance
vorapaxar sulfate
INN/Common name
vorapaxar
Pharmacotherapeutic Classes
Antithrombotic agents
Status
Withdrawn
Company
Merck Sharp Dohme Limited
Market Date
2015-01-19
2 of 2
Type
Paediatric investigation
Active Substance
Therapeutic Area
Cardiovascular diseases
Drug Form
Tablet
Administration Route
Oral use
Decision Type
PM: decision on the application for modification of an agreed PIP
Decision Date
2016-05-20

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Platelet Aggregation Inhibitors
Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)

7.2 FDA Pharmacological Classification

FDA UNII
ZCE93644N2
Active Moiety
VORAPAXAR
Pharmacological Classes
Established Pharmacologic Class [EPC] - Protease-activated Receptor-1 Antagonist
Pharmacological Classes
Mechanisms of Action [MoA] - Protease-activated Receptor-1 Antagonists
FDA Pharmacology Summary
Vorapaxar is a Protease-activated Receptor-1 Antagonist. The mechanism of action of vorapaxar is as a Protease-activated Receptor-1 Antagonist.

7.3 ATC Code

B01

B - Blood and blood forming organs

B01 - Antithrombotic agents

B01A - Antithrombotic agents

B01AC - Platelet aggregation inhibitors excl. heparin

B01AC26 - Vorapaxar

7.4 Absorption, Distribution and Excretion

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%.
Route of Elimination
Vorapaxar is primarily eliminated as its metabolite M19 through the feces (91.5%), and partially eliminated in the urine (8.5%).
Volume of Distribution
424 L

7.5 Metabolism / Metabolites

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

7.6 Biological Half-Life

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

7.7 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.

7.8 Transformations

8 Use and Manufacturing

8.1 Uses

8.1.1 Use Classification

Human drugs -> Antithrombotic agents -> Human pharmacotherapeutic group -> EMA Drug Category
Human Drugs -> EU pediatric investigation plans

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Health Hazard
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H371 (100%): May cause damage to organs [Warning Specific target organ toxicity, single exposure]

H373 (100%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P260, P264, P270, P273, P308+P316, P319, P391, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

STOT SE 2 (100%)

STOT RE 2 (100%)

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

10 Toxicity

10.1 Toxicological Information

10.1.1 Hepatotoxicity

Vorapaxar is associated with a low rate of serum enzyme elevations during therapy that was similar to the rate that occurred with placebo or comparator therapies. In a large controlled trial in over 10,000 patients monitored over a 2 year period, ALT elevations above 5 times the upper limit of normal occurred in 1% of vorapaxar vs 1.4% of placebo patients. In pooled analyses of laboratory studies from more than 39,000 patients receiving vorapaxar or placebo, GGT was the only liver test that was abnormal in a higher proportion of patients receiving vorapaxar (3.8%) than placebo (3.3%), and there were no reports of liver related serious adverse events or clinically apparent liver injury. Thus, liver injury from vorapaxar must be rare, if it occurs at all.

Likelihood score: E (unlikely cause of clinically apparent liver injury).

10.1.2 Protein Binding

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

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Wiley References

12.6 Chemical Co-Occurrences in Literature

12.7 Chemical-Gene Co-Occurrences in Literature

12.8 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Protein Bound 3D Structures

14.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

14.2 Chemical-Target Interactions

14.3 Drug-Drug Interactions

14.4 Drug-Food Interactions

  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Additive antiplatelet activity may increase the risk of bleeding. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
  • Avoid St. John's Wort. This herb induces the CYP3A metabolism of vorapaxar and may reduce its serum concentration.
  • Exercise caution with grapefruit products. Coadministration of vorapaxar with moderate CYP3A4 inhibitors does not require intervention, but coadministration with strong inhibitors should be avoided.
  • Take with or without food.

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 NCI Thesaurus Tree

16.3 ChEBI Ontology

16.4 KEGG: ATC

16.5 KEGG: Target-based Classification of Drugs

16.6 KEGG: Drug Groups

16.7 WHO ATC Classification System

16.8 FDA Pharm Classes

16.9 ChemIDplus

16.10 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

16.11 ChEMBL Target Tree

16.12 UN GHS Classification

16.13 NORMAN Suspect List Exchange Classification

16.14 EPA DSSTox Classification

16.15 PFAS and Fluorinated Organic Compounds in PubChem

16.16 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
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    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    Carbamic acid, N-[(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
    https://echa.europa.eu/substance-information/-/substanceinfo/100.116.767
    Carbamic acid, N-[(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 (EC: 612-523-7)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/51947
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. ChEBI
  8. FDA Pharm Classes
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  9. LiverTox
  10. NCI Thesaurus (NCIt)
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    https://www.cancer.gov/policies/copyright-reuse
  11. Open Targets
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    https://platform-docs.opentargets.org/licence
  12. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  13. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  14. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  15. IUPHAR/BPS Guide to PHARMACOLOGY
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    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  16. Therapeutic Target Database (TTD)
  17. DailyMed
  18. European Medicines Agency (EMA)
    LICENSE
    Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
    https://www.ema.europa.eu/en/about-us/legal-notice
  19. EU Clinical Trials Register
  20. WHO Anatomical Therapeutic Chemical (ATC) Classification
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    https://www.whocc.no/copyright_disclaimer/
  21. Japan Chemical Substance Dictionary (Nikkaji)
  22. KEGG
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    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
  23. Metabolomics Workbench
  24. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Vorapaxar
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  25. PharmGKB
    LICENSE
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    https://www.pharmgkb.org/page/policies
  26. Pharos
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  27. Protein Data Bank in Europe (PDBe)
  28. RCSB Protein Data Bank (RCSB PDB)
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  29. Springer Nature
  30. Thieme Chemistry
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  35. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
    Platelet Aggregation Inhibitors
    https://www.ncbi.nlm.nih.gov/mesh/68010975
  36. GHS Classification (UNECE)
  37. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  38. PATENTSCOPE (WIPO)
CONTENTS