Clopidogrel Bisulfate

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Cat Number

API120202666

CAS Number

120202-66-6

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Product Detail Description Scientific Support Customer Q&A

CAS Number

120202-66-6

EINECS

601-679-1

Storage

Store at room temperature

Synonyms

Clopidogrel bisulphate; Clopidogrel hemisulfate; clopidogrel hydrogen sulphate; Clopidogrel BMS; Isocover; Clopidogrel zentiva; SR-25990C

Molecular Formula

C16H18ClNO6S2

Molecular Weight

419.9

Smiles

COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O

Appearance

White to off-white crystalline powder

Melting Point

184℃

Boiling Point

447.3℃

General Description

Clopidogrel bisulfate is an oral thienopyridine antiplatelet agent that irreversibly inhibits platelet activation and aggregation. It is a prodrug requiring hepatic biotransformation to generate its active metabolite, which selectively targets the P2Y12 subtype of platelet adenosine diphosphate (ADP) receptors. This agent is a cornerstone of dual antiplatelet therapy following acute coronary syndromes and percutaneous coronary interventions.

Mechanism of Action

Following intestinal absorption, clopidogrel undergoes oxidative metabolism via cytochrome P450 enzymes, primarily CYP2C19, to produce an active thiol metabolite. This metabolite forms a covalent disulfide bond with the platelet P2Y12 ADP receptor, irreversibly blocking ADP binding and preventing ADP-mediated activation of the GPIIb/IIIa receptor complex. The resulting inhibition of platelet aggregation persists for the lifespan of the platelet, typically 7 to 10 days.

Application

It is indicated for the reduction of major adverse cardiovascular events in patients with recent myocardial infarction, stroke, or established peripheral arterial disease. It is also used in combination with aspirin for the management of acute coronary syndromes, including non-ST-elevation MI and ST-elevation MI managed with percutaneous coronary intervention. Genetic testing for CYP2C19 loss-of-function alleles may guide therapy in selected patients, as poor metabolizers have reduced antiplatelet efficacy.

In this multicenter, double‑blind, placebo‑controlled trial (OPT‑BIRISK), 7758 patients with acute coronary syndromes (ACS) at both high bleeding and ischemic risk who had completed 9–12 months of dual antiplatelet therapy (DAPT) after drug‑eluting stent implantation were randomized to clopidogrel plus placebo or clopidogrel plus aspirin for an additional 9 months. The primary bleeding endpoint (BARC types 2,3,5) occurred in 2.5% vs. 3.3% (HR 0.75; P=0.03). The key secondary endpoint (major adverse cardiac and cerebral events) was 2.6% vs. 3.5% (HR 0.74; P=0.02 for superiority). Extended clopidogrel monotherapy reduced clinically relevant bleeding without increasing ischemic events, establishing it as a superior maintenance strategy in this birisk population.

Fig. 1 Kaplan-Meier Curves for the Principal 9-Month Study Outcomes. (Li Y, et al., 2024)

References

Li Y, et al. Extended Clopidogrel Monotherapy vs DAPT in Patients With Acute Coronary Syndromes at High Ischemic and Bleeding Risk: The OPT-BIRISK Randomized Clinical Trial. JAMA Cardiol. 2024; 9(6):523-531.

Does Clopidogrel Bisulfate require protection from moisture during storage?

Yes, it is highly hygroscopic and can absorb moisture, leading to hydrolysis and formation of the carboxylic acid impurity. Store in tightly sealed, moisture-proof containers with desiccant.

What is the recommended storage temperature for Clopidogrel Bisulfate?

Store at controlled room temperature (15-25°C). Avoid temperatures above 30°C, which can accelerate degradation and cause polymorphic transformation.

Is Clopidogrel Bisulfate sensitive to light during long-term storage?

Yes, it is photosensitive. Prolonged UV exposure can cause photodegradation. Store in light-resistant containers, preferably amber glass or opaque HDPE.

How is the impurity clopidogrel carboxylic acid monitored during stability?

This primary hydrolysis product is specifically quantified using a stability-indicating HPLC method, ensuring it remains well below ICH limits throughout shelf life.