molecular formula C26H32ClNO6S2 B8563496 Clopidogrel Camphorsulfonate

Clopidogrel Camphorsulfonate

Cat. No.: B8563496
M. Wt: 554.1 g/mol
InChI Key: XEENARPWPCQXST-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Description

Clopidogrel Camphorsulfonate is a useful research compound. Its molecular formula is C26H32ClNO6S2 and its molecular weight is 554.1 g/mol. The purity is usually 95%.
BenchChem offers high-quality this compound suitable for many research applications. Different packaging options are available to accommodate customers' requirements. Please inquire for more information about this compound including the price, delivery time, and more detailed information at [email protected].

Scientific Research Applications

Pharmacological Properties

Clopidogrel is an inhibitor of platelet aggregation, primarily acting by blocking the binding of adenosine diphosphate (ADP) to its receptor on platelets. This mechanism reduces the likelihood of thrombus formation, which is crucial in preventing cardiovascular events such as myocardial infarction and stroke . The camphorsulfonate salt form enhances the stability and solubility of clopidogrel, making it suitable for pharmaceutical formulations .

Key Characteristics

  • Stability : Clopidogrel camphorsulfonate exhibits improved stability against moisture and heat compared to other salt forms .
  • Solubility : It has satisfactory water solubility, approximately 4.0 mg/ml, which facilitates its dissolution in pharmaceutical compositions .
  • Optical Purity : The salt can achieve high optical purity (≥98.5% enantiomeric excess), crucial for ensuring therapeutic efficacy .

Clinical Applications

This compound is primarily indicated for the prevention of atherothrombotic events in various clinical scenarios:

  • Acute Coronary Syndrome : It is used in combination with acetylsalicylic acid (ASA) for patients experiencing unstable angina or non-ST-segment elevation myocardial infarction .
  • Post-Myocardial Infarction : Administered to prevent further thrombotic events within 35 days following an acute myocardial infarction .
  • Ischemic Stroke : Effective in preventing recurrent strokes within six months after an initial event .
  • Peripheral Arterial Disease : Used for patients with established peripheral arterial disease to reduce cardiovascular complications .

Efficacy in Post-PCI Patients

A study highlighted that patients undergoing percutaneous coronary intervention (PCI) benefit significantly from clopidogrel therapy, showing a relative risk reduction of 30-85% in major adverse cardiovascular events compared to placebo . This underscores the importance of this compound in high-risk populations.

Pharmacogenetic Considerations

Research indicates that genetic variations affecting the CYP2C19 enzyme can influence the efficacy of clopidogrel. Patients with loss-of-function alleles may experience reduced therapeutic benefits, emphasizing the need for genotype-guided therapy in specific populations .

Comparison with Other Antiplatelet Agents

Clopidogrel has been compared with other antiplatelet medications like ticagrelor and aspirin. Evidence suggests that clopidogrel remains a critical option for patients who may not tolerate newer agents due to side effects or contraindications .

Properties

Molecular Formula

C26H32ClNO6S2

Molecular Weight

554.1 g/mol

IUPAC Name

(7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl)methanesulfonic acid;methyl 2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate

InChI

InChI=1S/C16H16ClNO2S.C10H16O4S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14;1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h2-5,7,9,15H,6,8,10H2,1H3;7H,3-6H2,1-2H3,(H,12,13,14)

InChI Key

XEENARPWPCQXST-UHFFFAOYSA-N

Canonical SMILES

CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C.COC(=O)C(C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3

Origin of Product

United States

Synthesis routes and methods

Procedure details

32 g (0.0994 mol) of (2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester is dissolved in 150 ml of acetone and to the solution 9.95 g (0.0397 mol) of laevorotatory 10-camphorsulfonic acid monohydrate is added. The homogenous reaction mixture is allowed to stay at room temperature. After 48 hours a few crystals appear. The mixture is concentrated by evaporation to 50 ml and allowed to stay at room temperature for 24 hours. The resulting crystals are filtered off, washed with acetone and dried. The crystals thus obtained are dissolved again in a very small amount (50 ml) of hot acetone and after cooling the crystals are filtered off, washed with acetone and dried. Thus the title compound is obtained. Yield: 88%. Mp.: 165° C. [α]20D=+24° (c=1.68 g/100 ml; methanol).
Name
(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester
Quantity
32 g
Type
reactant
Reaction Step One
Quantity
9.95 g
Type
reactant
Reaction Step One
Quantity
150 mL
Type
solvent
Reaction Step One
Quantity
50 mL
Type
solvent
Reaction Step Two
Yield
88%

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