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Prasugrel Hydrochloride (formerly also known as CS-747, PCR 4099 and LY640315), a piperazine derivative, is a novel and potent thienopyridine ADP receptor (P2Y12) antagonist used for the reduction of thrombotic cardiovascular events. Prasugrel was also approved for use in Europe in February 2009. On July 10, 2009, the FDA approved the use of prasugrel for the reduction of thrombotic cardiovascular events in patients with acute coronary syndrome who are to be managed with PCI.
Physicochemical Properties
| Exact Mass | 409.091 |
| CAS # | 389574-19-0 |
| Related CAS # | Prasugrel;150322-43-3;Prasugrel (Maleic acid);389574-20-3;Prasugrel-d5;1127252-92-9 |
| PubChem CID | 10158453 |
| Appearance | Light yellow to yellow solid powder |
| Boiling Point | 493.5ºC at 760 mmHg |
| Flash Point | 252.3℃ |
| LogP | 4.63 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 27 |
| Complexity | 555 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | FC1=CC=CC=C1C(C(C2CC2)=O)N3CCC4=C(C3)C=C(S4)OC(C)=O.Cl |
| InChi Key | JALHGCPDPSNJNY-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C20H20FNO3S.ClH/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;1H |
| Chemical Name | Ethanone, 2-(2-(acetyloxy)-6,7-dihydrothieno(3,2-c)pyridin-5(4H)-yl)-1-cyclopropyl-2-(2-fluorophenyl)-, hydrochloride |
| Synonyms | Prasugrel HydrochloridePrasugrel HClCS-747CS747CS 747PCR-4099PCR4099PCR 4099LY-640315LY640315LY 640315 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro |
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| ln Vivo | With an IC50 value of 1.8 μM, the active metabolite of prasugrel hydrochloride inhibits the in vitro platelet aggregation generated by adenosine ADP (10μM) in rat platelets[2]. In vivo, prasugrel hydrochloride exhibits a greater potency and works more quickly than clopidogrel. The active antiplatelet metabolite of prasugrel hydrochloride is produced by metabolic breakdown of the inactive prodrug in vivo. From the stomach, prasugrel hydrochloride is quickly absorbed. Maximum plasma levels of the active metabolite are reached within 1 hour following oral administration of standard-loading dosages of 60 mg, and maximal inhibition of platelet aggregation occurs within 1-2 hours[1]. | ||
| Animal Protocol |
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| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation No published information is available on the use of prasugrel during breastfeeding. Until more data become available, prasugrel should be used with caution during breastfeeding, especially while nursing a newborn or preterm infant. If it is used by a nursing mother, monitor the infant for bruising and bleeding. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. |
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| References |
[1]. Anti-platelet therapy: ADP receptor antagonists. Br J Clin Pharmacol. 2011 Oct;72(4):647-57. [2]. 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. |
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| Additional Infomation |
Prasugrel Hydrochloride is the hydrochloride salt form of prasugrel, an orally bioavailable thienopyridine, with antiplatelet activity. Upon oral administration, the active metabolite of prasugrel targets and irreversibly binds to the platelet receptor for adenosine diphosphate (ADP), thereby blocking the binding of ADP to its receptor. This inhibits ADP-mediated activation of the glycoprotein complex GPIIb/IIIa, fibrinogen binding to platelets and platelet adhesion and aggregation. This results in increased bleeding time. A piperazine derivative and PLATELET AGGREGATION INHIBITOR that is used to prevent THROMBOSIS in patients with ACUTE CORONARY SYNDROME; UNSTABLE ANGINA and MYOCARDIAL INFARCTION, as well as in those undergoing PERCUTANEOUS CORONARY INTERVENTIONS. See also: Prasugrel (has active moiety). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~41.67 mg/mL (~101.66 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.07 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.07 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (5.07 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |