Vorapaxar free base
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MedKoo CAT#: 330185

CAS#: 618385-01-6 (free base)

Description: Vorapaxar, also known as SCH 530348, is a thrombin receptor (protease-activated receptor, PAR-1) antagonist based on the natural product himbacine. vorapaxar was approved in 2014. Vorapaxar is a new anti-platelet drug that is part of the PAR-1 antagonist family, a new class of anti-platelet drug. It functions by inhibiting thrombin-related platelet aggregation. This mechanism works by a different pathway than other anti-platelet medications such as aspirin and P2Y12 inhibitors. Unlike many other medication, vorapaxar does not affect ADP-mediated platelet aggregation, coagulation parameters, or bleeding time.


Price and Availability

Size
Price

50mg
USD 450
500mg
USD 1950
Size
Price

100mg
USD 750
1g
USD 2950
Size
Price

200mg
USD 1250
2g
USD 5450

Vorapaxar free base, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 330185
Name: Vorapaxar free base
CAS#: 618385-01-6 (free base)
Chemical Formula: C29H33FN2O4
Exact Mass: 492.2424
Molecular Weight: 492.5914
Elemental Analysis: C, 70.71; H, 6.75; F, 3.86; N, 5.69; O, 12.99


Related CAS #: 705260-08-8 (sulfate)   618385-01-6 (free base)  

Synonym: SCH530348; SCH 530348; SCH-530348; Vorapaxar free base; Vorapaxar;

IUPAC/Chemical Name: 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

InChi Key: ZBGXUVOIWDMMJE-QHNZEKIYSA-N

InChi Code: 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

SMILES Code: O=C(OCC)N[C@H](CC1)C[C@](C[C@]23[H])([H])[C@]1([H])[C@H](/C=C/C4=NC=C(C5=CC=CC(F)=C5)C=C4)[C@]2([H])[C@@H](C)OC3=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934990300


References

1: Pang J, Hu P, Wang J, Jiang J, Lai J. Vorapaxar stabilizes permeability of the endothelial barrier under cholesterol stimulation via the AKT/JNK and NF κB signaling pathways. Mol Med Rep. 2019 Apr 30. doi: 10.3892/mmr.2019.10211. [Epub ahead of print] PubMed PMID: 31059055.

2: Patel SM, Morrow DA, Kidd SK, Goodrich EL, Scirica BM, Bonaca MP. Vorapaxar for secondary prevention in the elderly with peripheral artery disease: Insights from the TRA 2°P-TIMI 50 trial. Vasc Med. 2019 Apr;24(2):159-161. doi: 10.1177/1358863X19826681. Epub 2019 Mar 14. PubMed PMID: 30868939.

3: Ungar L, Clare RM, Rodriguez F, Kolls BJ, Armstrong PW, Aylward P, Held C, Moliterno DJ, Strony J, Van de Werf F, Wallentin L, White HD, Tricoci P, Harrington RA, Mahaffey KW, Melloni C. Stroke Outcomes With Vorapaxar Versus Placebo in Patients With Acute Coronary Syndromes: Insights From the TRACER Trial. J Am Heart Assoc. 2018 Dec 18;7(24):e009609. doi: 10.1161/JAHA.118.009609. PubMed PMID: 30526198; PubMed Central PMCID: PMC6405615.

4: Correa S, Bonaca MP, Scirica BM, Murphy SA, Goodrich EL, Morrow DA, O'Donoghue ML. Efficacy and safety of more potent antiplatelet therapy with vorapaxar in patients with impaired renal function. J Thromb Thrombolysis. 2019 Apr;47(3):353-360. doi: 10.1007/s11239-018-1779-y. PubMed PMID: 30511258.

5: ADVICE study group. Vorapaxar for HIV-associated inflammation and coagulopathy (ADVICE): a randomised, double-blind, placebo-controlled trial. Lancet HIV. 2018 Oct;5(10):e553-e559. doi: 10.1016/S2352-3018(18)30214-5. Epub 2018 Sep 23. Erratum in: Lancet HIV. 2019 Jan 25;:. PubMed PMID: 30257802; PubMed Central PMCID: PMC6237199.

6: Waasdorp M, Duitman J, Florquin S, Spek CA. Vorapaxar treatment reduces mesangial expansion in streptozotocin-induced diabetic nephropathy in mice. Oncotarget. 2018 Apr 24;9(31):21655-21662. doi: 10.18632/oncotarget.25069. eCollection 2018 Apr 24. PubMed PMID: 29774092; PubMed Central PMCID: PMC5955164.

7: Tawfik B, Pollard E, Shen YM. The Novel Protease-Activated Receptor 1 Antagonist Vorapaxar as a Treatment for Thrombosis in Afibrinogenemia. Semin Thromb Hemost. 2018 Jun;44(4):404-406. doi: 10.1055/s-0038-1654715. Epub 2018 May 15. PubMed PMID: 29763961.

8: Nair AS. Vorapaxar: The missing link in antiplatelet therapy! J Anaesthesiol Clin Pharmacol. 2017 Apr-Jun;33(2):269-270. doi: 10.4103/joacp.JOACP_363_16. PubMed PMID: 28781465; PubMed Central PMCID: PMC5520612.

9: Kei A, Elisaf M. Vorapaxar in secondary prevention: where we stand. Curr Med Res Opin. 2017 Nov;33(11):2077-2079. doi: 10.1080/03007995.2017.1341405. Epub 2017 Jul 6. PubMed PMID: 28604119.

10: Moon JY, Franchi F, Rollini F, Angiolillo DJ. Role for Thrombin Receptor Antagonism With Vorapaxar in Secondary Prevention of Atherothrombotic Events: From Bench to Bedside. J Cardiovasc Pharmacol Ther. 2018 Jan;23(1):23-37. doi: 10.1177/1074248417708617. Epub 2017 May 31. Review. PubMed PMID: 28565918.

11: Anderson MS, Kosoglou T, Statkevich P, Li J, Rotonda J, Meehan AG, Cutler DL. No Pharmacokinetic Drug-Drug Interaction Between Prasugrel and Vorapaxar Following Multiple-Dose Administration in Healthy Volunteers. Clin Pharmacol Drug Dev. 2018 Feb;7(2):143-150. doi: 10.1002/cpdd.354. Epub 2017 Apr 12. PubMed PMID: 28403576; PubMed Central PMCID: PMC5811915.

12: Du M, Chase M, Oguz M, Davies G. State transition model: vorapaxar added to standard antiplatelet therapy to prevent thrombosis post myocardial infarction or peripheral artery disease. Curr Med Res Opin. 2017 Sep;33(9):1535-1543. doi: 10.1080/03007995.2017.1301902. Epub 2017 Mar 12. PubMed PMID: 28277861.

13: Serebruany VL, Fortmann SD, Hanley DF, Kim MH. Vorapaxar and Amyotrophic Lateral Sclerosis: Coincidence or Adverse Association? Am J Ther. 2017 Mar/Apr;24(2):e139-e143. doi: 10.1097/MJT.0000000000000395. Review. PubMed PMID: 28267691.

14: Perez-Rivera JA, Monedero-Campo J, Cieza-Borrella C, Ruiz-Perez P. Pharmacokinetic drug evaluation of vorapaxar for secondary prevention after acute coronary syndrome. Expert Opin Drug Metab Toxicol. 2017 Mar;13(3):339-350. doi: 10.1080/17425255.2017.1289175. Epub 2017 Feb 7. Review. PubMed PMID: 28135897.

15: Gryka RJ, Buckley LF, Anderson SM. Vorapaxar: The Current Role and Future Directions of a Novel Protease-Activated Receptor Antagonist for Risk Reduction in Atherosclerotic Disease. Drugs R D. 2017 Mar;17(1):65-72. doi: 10.1007/s40268-016-0158-4. Review. PubMed PMID: 28063023; PubMed Central PMCID: PMC5318326.

16: Sharma A, Helft G, Garg A, Agrawal S, Chatterjee S, Lavie CJ, Goel S, Mukherjee D, Marmur JD. Safety and efficacy of vorapaxar in secondary prevention of atherosclerotic disease: A meta-analysis of randomized control trials. Int J Cardiol. 2017 Jan 15;227:617-624. doi: 10.1016/j.ijcard.2016.10.088. Epub 2016 Oct 29. PubMed PMID: 27810296.

17: Safian RD. Appropriate Use of Vorapaxar in Patients With Peripheral Artery Disease. JACC Cardiovasc Interv. 2016 Oct 24;9(20):2165-2166. doi: 10.1016/j.jcin.2016.08.042. PubMed PMID: 27765313.

18: Bonaca MP, Creager MA, Olin J, Scirica BM, Gilchrist IC Jr, Murphy SA, Goodrich EL, Braunwald E, Morrow DA. Peripheral Revascularization in Patients With Peripheral Artery Disease With Vorapaxar: Insights From the TRA 2°P-TIMI 50 Trial. JACC Cardiovasc Interv. 2016 Oct 24;9(20):2157-2164. doi: 10.1016/j.jcin.2016.07.034. PubMed PMID: 27765312.

19: Armaganijan LV, Alexander KP, Huang Z, Tricoci P, Held C, Van de Werf F, Armstrong PW, Aylward PE, White HD, Moliterno DJ, Wallentin L, Chen E, Harrington RA, Strony J, Mahaffey KW, Lopes RD. Effect of age on efficacy and safety of vorapaxar in patients with non-ST-segment elevation acute coronary syndrome: Insights from the Thrombin Receptor Antagonist for Clinical Event Reduction in Acute Coronary Syndrome (TRACER) trial. Am Heart J. 2016 Aug;178:176-84. doi: 10.1016/j.ahj.2016.05.012. Epub 2016 Jun 9. PubMed PMID: 27502866.

20: Moschonas IC, Tselepis AD. Increased Benefit With Vorapaxar Use in Patients With a History of Myocardial Infarction and Diabetes Mellitus: What the Data Show Us. J Cardiovasc Pharmacol Ther. 2017 Mar;22(2):133-141. doi: 10.1177/1074248416662347. Epub 2016 Aug 11. PubMed PMID: 27489245.