Clopidogrel | Antiplatelet Agent | CAS 113665-84-2 | P2Y₁₂ Inhibitor
Product Name: Clopidogrel
CAS No.: 113665-84-2
Molecular Formula: C₁₆H₁₆ClNO₂S
Appearance: White or almost white crystalline powder
Solubility: Practically insoluble in water at neutral pH; soluble in methanol. Often used as salts (bisulfate or hydrochloride) to improve solubility and bioavailability.
1. Introduction
Clopidogrel is an antiplatelet agent belonging to the thienopyridine class. It is a prodrug that, after metabolic activation in the liver, irreversibly inhibits P2Y₁₂ platelet receptors, preventing ADP-induced platelet aggregation. Clopidogrel is widely used for the prevention of atherothrombotic events in patients with coronary artery disease, prior myocardial infarction, stroke, or peripheral arterial disease.
Platelet aggregation plays a central role in the pathogenesis of atherothrombosis, which underlies serious cardiovascular events such as myocardial infarction and ischemic stroke. Clopidogrel, due to its ability to suppress platelet activation and aggregation, has become a key drug for secondary prevention of these conditions and is widely used in combination with aspirin (dual antiplatelet therapy) following percutaneous coronary interventions.
2. Chemical Structure & Synthesis
Clopidogrel is a thieno[3,2-c]pyridine derivative. It exists as a racemic mixture, but only the S-enantiomer exhibits antiplatelet activity after metabolic activation.
Molecular Formula: C₁₆H₁₆ClNO₂S
The synthesis of clopidogrel involves several steps, the key of which is the construction of the thienopyridine core followed by the introduction of ester and chlorophenyl groups. Special attention is given to obtaining the optically active S-enantiomer when used as a single isomer (e.g., clopidogrel bisulfate).
3. Physicochemical Properties & Pharmacology
| Property | Description |
|---|---|
| Appearance | White or almost white crystalline powder |
| Solubility | Practically insoluble in water (neutral pH); soluble in methanol |
| Mechanism of Action | Prodrug. Active metabolite selectively and irreversibly binds to P2Y₁₂ receptors on platelet surfaces, blocking ADP binding and subsequent ADP-dependent activation of the GPIIb/IIIa complex, leading to inhibition of platelet aggregation |
| Absorption | Rapidly absorbed after oral administration |
| Metabolism | Hepatic (cytochrome P450, primarily CYP2C19) to active metabolite |
| Excretion | Urine and feces |
| Onset | Inhibition of platelet aggregation occurs within hours; maximum effect after several days of regular use |
4. Applications
| Indication | Use |
|---|---|
| Secondary Prevention of Atherothrombotic Events | Patients with prior myocardial infarction (several days to 35 days); ischemic stroke (7 days to 6 months); established peripheral arterial disease |
| Acute Coronary Syndrome (ACS) | Non-ST-segment elevation ACS (unstable angina, non-Q-wave MI) – in combination with aspirin; ST-segment elevation ACS – in combination with aspirin for patients receiving medical treatment or percutaneous coronary intervention (PCI) |
| Post-PCI / Stenting | Prevention of thrombotic complications after coronary stenting (as part of dual antiplatelet therapy) |
5. Conclusion
Clopidogrel is an important antiplatelet drug proven effective in reducing the risk of atherothrombotic complications in a wide range of patients with cardiovascular disease. Its use, particularly as part of dual antiplatelet therapy, has become the standard of care for acute coronary syndrome and after coronary stenting. However, individual differences in drug metabolism (CYP2C19 genetic polymorphism) and bleeding risk should be considered when prescribing.
