Prasugrel | CAS#150322-43-3 | Platelet inhibitor

MedKoo Cat#: 315263 | Name: Prasugrel free base

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Prasugrel is a novel platelet inhibitor for acute coronary syndromes planned for percutaneous coronary intervention (PCI). Prasugrel is a prodrug form of the platelet purinergic P2Y12 receptor antagonist R-99224. Prasugrel (0.3 and 3 mg/kg) inhibits ex vivo washed platelet aggregation in rat platelet rich-plasma. In vivo, prasugrel prevents thrombus formation (ED50 = 0.68 mg/kg) and increases tail bleeding time in rats. Formulations containing prasugrel have been used in the prevention of blood clots.

Chemical Structure

Prasugrel free base

CAS#150322-43-3 (free base)

Theoretical Analysis

MedKoo Cat#: 315263

Name: Prasugrel free base

CAS#: 150322-43-3 (free base)

Chemical Formula: C20H20FNO3S

Exact Mass: 373.1148

Molecular Weight: 373.44

Elemental Analysis: C, 64.32; H, 5.40; F, 5.09; N, 3.75; O, 12.85; S, 8.59

Price and Availability

Size	Price	Availability
25mg	USD 450.00	2 Weeks
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks
200mg	USD 1,650.00	2 Weeks

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Related CAS #

389574-19-0 (HCl) 150322-43-3 (free base)

Synonym

CS 747; CS-747; CS747; LY640315; LY-640315; LY 640315; Prasugrel free base;

IUPAC/Chemical Name

5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate

InChi Key

DTGLZDAWLRGWQN-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3

SMILES Code

CC(OC(S1)=CC2=C1CCN(C(C3=CC=CC=C3F)C(C4CC4)=O)C2)=O

Appearance

White 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

>2 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).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Prasugrel is an orally active and potent P2Y12 receptor antagonist, and inhibits ADP-induced platelet aggregation.

In vitro activity:

Prasugrel is a novel orally active thienopyridine prodrug with potent and long-lasting antiplatelet effects. Platelet inhibition reflects inhibition of P2Y(12) receptors by its active metabolite (AM). Previous studies have shown that the antiplatelet potency of prasugrel is at least 10 times higher than that of clopidogrel in rats and humans, but the mechanism of its higher potency has not yet been fully elucidated. In rat platelets, prasugrel AM inhibited in vitro platelet aggregation induced by adenosine 5'-diphosphate (ADP) (10 microm) with an IC(50) value of 1.8 microm. Reference: J Thromb Haemost. 2007 Jul;5(7):1545-51. https://pubmed.ncbi.nlm.nih.gov/17456192/

In vivo activity:

In the present study, effects of prasugrel on ex vivo platelet aggregation were examined in wild type (WT) and P2Y(12)(-/-) mice. In WT mice, prasugrel showed platelet inhibition that was 8.2 times more potent than clopidogrel. In P2Y(12)(-/-) mice, ADP induced platelet aggregation was minimal, and its extent was similar to that in prasugrel-treated WT mice. In addition, no further inhibition of platelet aggregation was observed after administration of prasugrel to P2Y(12)(-/-) mice. Furthermore, prasugrel-treated WT mice showed similar aggregation patterns using collagen- and murine PAR-4 agonist peptide to those of P2Y(12)(-/-) mice treated with vehicle or prasugrel. Reference: Biochem Pharmacol. 2007 Oct 1;74(7):1003-9. https://pubmed.ncbi.nlm.nih.gov/17681285/

	Solvent	mg/mL	mM
Solubility
	DMF	5.0	13.39
	DMSO	56.8	152.04
	Ethanol	8.0	21.42
	PBS (pH 7.2)	0.3	0.67

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 373.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Johnston LR, La Flamme AC, Larsen PD, Harding SA. Prasugrel inhibits platelet-enhanced pro-inflammatory CD4+ T cell responses in humans. Atherosclerosis. 2015 Mar;239(1):283-6. doi: 10.1016/j.atherosclerosis.2015.01.006. Epub 2015 Jan 14. PMID: 25635327. 2. Sugidachi A, Ogawa T, Kurihara A, Hagihara K, Jakubowski JA, Hashimoto M, Niitsu Y, Asai F. The greater in vivo antiplatelet effects of prasugrel as compared to clopidogrel reflect more efficient generation of its active metabolite with similar antiplatelet activity to that of clopidogrel's active metabolite. J Thromb Haemost. 2007 Jul;5(7):1545-51. doi: 10.1111/j.1538-7836.2007.02598.x. Epub 2007 Apr 19. Erratum in: J Thromb Haemost. 2007 Sep;5(9):1995. PMID: 17456192. 3. Ogawa T, Hashimoto M, Niitsu Y, Jakubowski JA, Tani Y, Otsuguro K, Asai F, Sugidachi A. Effects of prasugrel, a novel P2Y(12) inhibitor, in rat models of cerebral and peripheral artery occlusive diseases. Eur J Pharmacol. 2009 Jun 10;612(1-3):29-34. doi: 10.1016/j.ejphar.2009.03.073. Epub 2009 Apr 6. PMID: 19356727. 4. Hashimoto M, Sugidachi A, Isobe T, Niitsu Y, Ogawa T, Jakubowski JA, Asai F. The influence of P2Y12 receptor deficiency on the platelet inhibitory activities of prasugrel in a mouse model: evidence for specific inhibition of P2Y12 receptors by prasugrel. Biochem Pharmacol. 2007 Oct 1;74(7):1003-9. doi: 10.1016/j.bcp.2007.06.027. Epub 2007 Jun 23. PMID: 17681285.

In vitro protocol:

In vivo protocol:

1. Ogawa T, Hashimoto M, Niitsu Y, Jakubowski JA, Tani Y, Otsuguro K, Asai F, Sugidachi A. Effects of prasugrel, a novel P2Y(12) inhibitor, in rat models of cerebral and peripheral artery occlusive diseases. Eur J Pharmacol. 2009 Jun 10;612(1-3):29-34. doi: 10.1016/j.ejphar.2009.03.073. Epub 2009 Apr 6. PMID: 19356727. 2. Hashimoto M, Sugidachi A, Isobe T, Niitsu Y, Ogawa T, Jakubowski JA, Asai F. The influence of P2Y12 receptor deficiency on the platelet inhibitory activities of prasugrel in a mouse model: evidence for specific inhibition of P2Y12 receptors by prasugrel. Biochem Pharmacol. 2007 Oct 1;74(7):1003-9. doi: 10.1016/j.bcp.2007.06.027. Epub 2007 Jun 23. PMID: 17681285.

1: Nambu K, Misaki K, Uno T, Tsutsui T, Kamide T, Nakada M. Periprocedural antiplatelet medication assessed by VerifyNow for neuroendovascular treatment: Comparison of prasugrel with clopidogrel. Interv Neuroradiol. 2023 Dec 11:15910199231219019. doi: 10.1177/15910199231219019. Epub ahead of print. PMID: 38082549. 2: Flynn LM, Mohamed E, Dobbs N, Nania A, Du Plessis J, Keston PM, Downer JJ. Safety of dual antiplatelet therapy using aspirin and low-dose Prasugrel with platelet reactivity testing in flow diverter treatment of intracranial aneurysms. Interv Neuroradiol. 2023 Nov 29:15910199231217142. doi: 10.1177/15910199231217142. Epub ahead of print. PMID: 38031444. 3: Kitahara H, Tateishi K, Shiko Y, Inaba Y, Kobayashi Y, Inoue T. Correction: Comparison of short-term clinical outcomes between low-dose prasugrel and clopidogrel as part of triple antithrombotic therapy in patients requiring oral anticoagulant therapy and percutaneous coronary intervention. PLoS One. 2023 Oct 31;18(10):e0293937. doi: 10.1371/journal.pone.0293937. Erratum for: PLoS One. 2022 Jul 28;17(7):e0272140. PMID: 37906590; PMCID: PMC10617684. 4: Suyama K, Nakahara I, Matsumoto S, Morioka J, Tanabe J, Hasebe A, Watanabe S. Efficacy and Safety of Dual Antiplatelet Therapy with the Routine Use of Prasugrel for Flow Diversion of Cerebral Unruptured Aneurysms. Clin Neuroradiol. 2023 Oct 17. doi: 10.1007/s00062-023-01355-2. Epub ahead of print. PMID: 37847296. 5: Choi HH, Lee HS, Lee SH, Kim K, Cho WS, Kim JE, Kang HS. Delayed ischemic events with low-dose prasugrel medication for stent-assisted coil embolization in intracranial aneurysm patients. Neurosurg Focus. 2023 Oct;55(4):E12. doi: 10.3171/2023.7.FOCUS22654. PMID: 37778045. 6: Institute for Quality and Efficiency in Health Care (IQWiG). Clopidogrel, prasugrel and ticagrelor for acute coronary syndrome: IQWiG Reports – Commission No. A21-41 [Internet]. Cologne (Germany): Institute for Quality and Efficiency in Health Care (IQWiG); 2023 Sep 27. PMID: 37878733. 7: Shah RP, Shafiq A, Hamza M, Maniya MT, Duhan S, Keisham B, Patel B, Alamzaib SM, Yashi K, Uppal D, Sattar Y, Tiwari D, Paul TK, AlJaroudi W, Alraies MC. Ticagrelor Versus Prasugrel in Patients With Acute Coronary Syndrome: A Systematic Review and Meta-Analysis. Am J Cardiol. 2023 Nov 15;207:206-214. doi: 10.1016/j.amjcard.2023.08.117. Epub 2023 Sep 24. PMID: 37751668. 8: Paszek E, Natorska J, Ząbczyk M, Klajmon A, Undas A. Therapy with ticagrelor/prasugrel is associated with enhanced fibrinolysis and suppressed platelet activation as compared to clopidogrel in chronic coronary syndrome. Kardiol Pol. 2023;81(11):1130-1133. doi: 10.33963/v.kp.97391. Epub 2023 Sep 18. PMID: 37718582. 9: Jang KM, Jang JS, Choi H, Cho YD. Safety and efficacy of tailored antiplatelet therapy using prasugrel or ticagrelor based on clopidogrel responsiveness in endovascular treatment for intracranial aneurysms: a meta- analysis. J Neurointerv Surg. 2023 Aug 23:jnis-2023-020548. doi: 10.1136/jnis-2023-020548. Epub ahead of print. PMID: 37611940. 10: Franchi F, Rollini F, Ortega-Paz L, Been L, Giordano S, Galli M, Ghanem G, Garabedian H, Al Saleh T, Uzunoglu E, Rivas A, Pineda AM, Suryadevara S, Soffer D, Zenni MM, Mahowald M, Reiter B, Jilma B, Angiolillo DJ. Switching From Cangrelor to Prasugrel in Patients Undergoing Percutaneous Coronary Intervention: The Switching Antiplatelet-6 (SWAP-6) Study. JACC Cardiovasc Interv. 2023 Oct 23;16(20):2528-2539. doi: 10.1016/j.jcin.2023.08.009. Epub 2023 Aug 21. PMID: 37609698. 11: Yildirim M, Mueller-Hennessen M, Milles BR, Biener M, Hund H, Frey N, Giannitsis E, Salbach C. Real-World Evidence on Disparities on the Initiation of Ticagrelor Versus Prasugrel in Patients With Acute Coronary Syndrome. J Am Heart Assoc. 2023 Aug 15;12(16):e030879. doi: 10.1161/JAHA.123.030879. Epub 2023 Aug 10. PMID: 37581388; PMCID: PMC10492934. 12: Asai K, Taniguchi M, Nakamura H, Tateishi A, Irizato N, Okubata H, Fukuya S, Yoshimura K, Yamamoto K, Kishima H, Wakayama A. Safety and Efficacy of Prasugrel Administration in Emergent Endovascular Treatment for Intracranial Atherosclerotic Disease. J Neuroendovasc Ther. 2023;17(7):125-131. doi: 10.5797/jnet.oa.2023-0008. Epub 2023 Jun 2. PMID: 37546344; PMCID: PMC10400910. 13: de Castro-Afonso LH, Machado JP, Nakiri GS, Abud TG, Monsignore LM, Freitas RK, de Oliveira RS, Colli BO, Abud DG. Two year follow-up of distal unruptured intracranial aneurysms treated with a surface modified flow diverter under prasugrel monotherapy. J Neurointerv Surg. 2023 Jul 31:jnis-2023-020397. doi: 10.1136/jnis-2023-020397. Epub ahead of print. PMID: 37524519. 14: Şen S. Comparison of bleeding risk between standard ticagrelor and prasugrel therapies without de-escalation strategy. Eur Heart J. 2023 Aug 22;44(32):3100-3101. doi: 10.1093/eurheartj/ehad432. PMID: 37477371. 15: Kang J, Park KW, Kim HS. Comparison of standard ticagrelor and prasugrel therapies based on previous trials. Eur Heart J. 2023 Aug 22;44(32):3102-3103. doi: 10.1093/eurheartj/ehad433. PMID: 37477206. 16: Agrawal RS, Yusuf J, Mahajan B, Mehta V, Mandal S, Mukhopadhyay S. Effect of prasugrel versus ticagrelor on coronary microcirculation in patients undergoing pharmacoinvasive strategy - acute and short-term results. Coron Artery Dis. 2023 Sep 1;34(6):381-388. doi: 10.1097/MCA.0000000000001265. Epub 2023 Jul 4. PMID: 37471285. 17: Chiarito M, Cao D, Sartori S, Zhang Z, Vogel B, Spirito A, Smith KF, Weintraub W, Strauss C, Toma C, DeFranco A, Effron MB, Stefanini G, Keller S, Kapadia S, Rao SV, Henry TD, Pocock S, Sharma S, Dangas G, Kini A, Baber U, Mehran R. Thrombotic risk in patients with acute coronary syndromes discharged on prasugrel or clopidogrel: results from the PROMETHEUS study. Eur Heart J Acute Cardiovasc Care. 2023 Sep 25;12(9):594-603. doi: 10.1093/ehjacc/zuad083. PMID: 37459570. 18: Ray A, Najmi A, Khandelwal G, Jhaj R, Sadasivam B. Usefulness of the PRECISE-DAPT score at differentiating between ticagrelor and prasugrel for dual antiplatelet therapy initiation. J Thromb Thrombolysis. 2023 Oct;56(3):411-413. doi: 10.1007/s11239-023-02857-z. Epub 2023 Jul 4. PMID: 37402078. 19: Hong N, Kim SB, Yang HJ, Son YJ. Variability of response on prophylactic prasugrel for endovascular treatment of intracranial aneurysms: Clinical implications. PLoS One. 2023 Jun 23;18(6):e0287190. doi: 10.1371/journal.pone.0287190. PMID: 37352283; PMCID: PMC10289319. 20: Goto H, Saito Y, Matsumoto T, Sato T, Yamashita D, Suzuki S, Wakabayashi S, Kitahara H, Sano K, Kobayashi Y. Differential Impact of Clinical Factors for Predicting High Platelet Reactivity on Clinical Outcomes in Acute Myocardial Infarction Patients Treated With Clopidogrel and Prasugrel. J Atheroscler Thromb. 2023 Dec 1;30(12):1791-1802. doi: 10.5551/jat.64217. Epub 2023 Jun 13. PMID: 37316266; PMCID: PMC10703564.