Prasugrel Hydrochloride

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Cat Number

API0232150

CAS Number

389574-19-0

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CAS Number

389574-19-0

EINECS

627-126-4

Storage

Store at room temperature

Synonyms

Prasugrel HCl; Prasu doc; LY 640315; DTXSID1049067; G89JQ59I13; DTXCID6028993

Molecular Formula

C20H21ClFNO3S

Molecular Weight

409.9

Smiles

CC(=O)OC1=CC2=C(S1)CCN(C2)C(C3=CC=CC=C3F)C(=O)C4CC4.Cl

Appearance

White to light brown crystalline solid

General Description

Prasugrel hydrochloride is a thienopyridine prodrug that irreversibly inhibits the platelet P2Y12 ADP receptor. Its structure contains a cyclopropyl group and a fluorine atom, which enhance metabolic conversion to the active metabolite. The hydrochloride salt provides stability. Prasugrel is more potent and has a faster onset than clopidogrel due to more efficient hepatic activation.

Mechanism of Action

Prasugrel is converted to its active metabolite via two sequential cytochrome P450 reactions (primarily CYP3A4 and CYP2B6, with minor contributions from CYP2C9 and CYP2C19). The active metabolite forms a covalent disulfide bond with the P2Y12 receptor on platelets, irreversibly blocking ADP binding and preventing GPIIb/IIIa receptor activation. This inhibits platelet aggregation for the lifespan of the platelet (7‑10 days).

Application

Prasugrel is indicated for the prevention of thrombotic cardiovascular events (stent thrombosis, myocardial infarction, stroke) in patients with acute coronary syndrome (ACS) undergoing percutaneous coronary intervention (PCI). It is more effective than clopidogrel but carries a higher risk of bleeding, particularly in patients with low body weight, age >75, or history of stroke or TIA.

This meta‑analysis of 11 randomized trials (6,098 patients with acute coronary syndrome, weighted mean follow‑up 11 months) compared prasugrel and ticagrelor. No significant difference was found in the primary composite endpoint of myocardial infarction, stroke, or cardiovascular death (RR 1.17, 95% CI 0.96‑1.42). Secondary outcomes (stroke, cardiovascular death, major bleeding, stent thrombosis, all‑cause death) also did not differ significantly. However, ticagrelor was associated with a higher risk of myocardial infarction (RR 1.38, 95% CI 1.05‑1.81, p=0.02). The authors conclude that prasugrel may offer an advantage in reducing MI risk.

Fig. 1 Central illustration: comparing the efficacy of prasugrel and ticagrelor among acute coronary syndrome patients. (Fong LCW, et al., 2022)

References

Fong LCW, et al. Comparison of Prasugrel and Ticagrelor for Patients with Acute Coronary Syndrome: A Systematic Review and Meta-Analysis. Cardiology. 2022;147(1):1-13.

In STEMI patients receiving prasugrel, chewed tablets produced higher levels of the intermediate metabolite (PIM; R‑95913) than integral tablets (AUC 73 vs. 33 ng·h/mL, P<0.05). PIM negatively correlated with platelet aggregation inhibition. In vitro, PIM dose‑dependently antagonized the anti‑aggregatory effect of the active metabolite (PAM; R‑138727) (maximum effect ‑49.5%, P<0.001). Molecular dynamics simulations showed PIM competes reversibly with PAM at the same P2Y₁₂ binding site. PIM is an antagonist of prasugrel’s active metabolite, reducing its antiplatelet activity.

Fig. 2 Structural in silico analysis of inactive and active metabolites of prasugrel. (Minuz P, et al., 2025)

References

Minuz P, et al. Prasugrel Intermediate Metabolite Modulates Platelet Inhibition by Negatively Interfering With an Active Metabolite: An Ex Vivo, In Vitro, and In Silico Study. Arterioscler Thromb Vasc Biol. 2025;45(5):792-804.

Does Prasugrel Hydrochloride require protection from moisture during storage?

Yes, it is hygroscopic and prone to hydrolysis of the thiophene ester. Store in tightly sealed, moisture-proof containers with desiccant.

What is the recommended storage temperature for Prasugrel Hydrochloride?

Store at controlled room temperature (15-25°C). Avoid temperatures above 30°C, which accelerate degradation to the inactive thiolactone impurity.

Is Prasugrel Hydrochloride stable in tablet formulations with standard excipients?

Yes, when formulated with moisture-protective packaging (e.g., blisters with desiccant).

How is the impurity prasugrel thiolactone (hydrolysis product) monitored?

This primary degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within ICH limits.