(S)-(+)-Clopidogrel (hydrogen sulfate)

Clopidogrel (INN) is an oral, thienopyridine-class antiplatelet agent used to inhibit blood clots in coronary artery disease, peripheral vascular disease, cerebrovascular disease, and to prevent myocardial infarction (heart attack) and stroke. It is marketed by Bristol-Myers Squibb and Sanofi under the trade name Plavix. The drug works by irreversibly inhibiting a receptor called P2Y12, an adenosine diphosphate (ADP) chemoreceptor on platelet cell membranes. Clopidogrel acts by inhibiting the ADP receptor on platelet cell membranes. It is a prodrug, which requires CYP2C19 for its activation.

Product information

CAS Number: 120202-66-6

Molecular Weight: 419.90

Formula: C16H18ClNO6S2

Synonym:

(S)-(+)-Clopidogrel bisulfate

Plavix

Chemical Name: methyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate; sulfuric acid

Smiles: COC(=O)[C@H](C1=CC=CC=C1Cl)N1CC2C=CSC=2CC1.OS(O)(=O)=O

InChiKey: FDEODCTUSIWGLK-RSAXXLAASA-N

InChi: InChI=1S/C16H16ClNO2S.H2O4S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14;1-5(2,3)4/h2-5,7,9,15H,6,8,10H2,1H3;(H2,1,2,3,4)/t15-;/m0./s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO, not in water

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

DNA fragmentation was found to be increased as a response to 7.5 µM, 40 µM and 75 µM clopidogrel treatment compared to non-treated control groups in AML-12 hepatocytes (p<0.01, p<0.001, p<0.01 respectively) and 3T3-L1 adipocytes (p<0.001, p<0.001 and p<0.001 respectively). DNA damage levels as a response to clopidogrel treatment was found to be higher in 3T3-L1 adipocytes than AML-12 hepatocytes.

In Vivo:

The effects of intravenous ADP infusions of 2-8mg/kg/hour were examined in anesthetized Wistar rats that were untreated or chronically pretreated with clopidogrel, 20mg/kg/24hours, a selective P2Y12-R antagonist. ADP induced a gradual, dose-dependent 15% decrease of mean arterial pressure, a sustained increase of renal blood flow and a 25% decrease in renal vascular resistance. Clopidogrel pretreatment attenuated the mean arterial pressure decrease, and did not significantly alter renal blood flow or renal vascular resistance.

References:

1. Khodor S, Castro M, McNamara C, Chaulagain CP. Clopidogrel-induced refractory thrombotic thrombocytopenic purpura successfully treated with rituximab. Hematol Oncol Stem Cell Ther. 2015 Dec 2. pii: S1658-3876(15)00105-3.
2. Zhang JR, Wang DQ, Du J, Qu GS, Du JL, Deng SB, Liu YJ, Cai JX, She Q. Efficacy of Clopidogrel and Clinical Outcome When Clopidogrel Is Coadministered With Atorvastatin and Lansoprazole: A Prospective, Randomized, Controlled Trial. Medicine (Baltimore). 2015 Dec;94(50):e2262.
3. Yang YG, Zhang M, Jiang N, Song LX, Xu XT, Di XH, Xu L, Xu J, Zhao GT. Bioequivalence of clopidogrel hydrogen sulfate tablets in healthy Chinese volunteers. Genet Mol Res. 2015 Dec 14;14(4):16736-43.

Products are for research use only. Not for human use.