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Clopidogrel(CAS No. 113665-84-2)

Clopidogrel C16H16ClNO2S (cas 113665-84-2) Molecular Structure

113665-84-2 Structure

Identification and Related Records

【Name】
Clopidogrel
【CAS Registry number】
113665-84-2
【Synonyms】
Clopidogre
Thieno(3,2-c)pyridine-5(4H)-acetic acid, alpha-(2-chlorophenyl)-6,7-dihydro-, methyl ester, (S)-
methyl (2S)-2-(2-chlorophenyl)-2-(9-thia-4-azabicyclo[4.3.0]nona-7,10-dien-4-yl)acetate
Thieno[3,2-c]pyridine-5(4H)-acetic acid,R-(2-chlorophenyl)-6,7-dihydro-,methyl ester,(RS)-
Methyl (+)-(S)-alpha-(o-chlorophenyl)-6,7-dihydrothieno(3,2-c)pyridine-5(4H)-acetate
Clopidogrel (For R&D)
【Molecular Formula】
C16H16ClNO2S (Products with the same molecular formula)
【Molecular Weight】
321.82
【Inchi】
InChI=1/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/m0/s1
【Canonical SMILES】
COC(=O)C(C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3
【Isomers smiles】
COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3
【MOL File】
113665-84-2.mol

Chemical and Physical Properties

【Appearance】
white powder
【Density】
1.317g/cm3
【Boiling Point】
423.7°Cat760mmHg
【Flash Point】
210°C

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22
【Safety Statements 】
26-36
【HazardClass】
22-36/37/38
【Safety】

Hazard Codes:?HarmfulXn
Risk Statements: 22-36/37/38
R22:? Harmful if swallowed?
R36/37/38:? Irritating to eyes, respiratory system and skin?
Safety Statements: 26-36
S26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
S36:? Wear suitable protective clothing?

【Formulations/Preparations】
Oral: Tablets: 75 mg (of clopidogrel) Plavix, (Sanofi-Aventis) (also promoted by Bristol-Myers Squibb). /Clopidogrel bisulfate/
Trade names (hydrogen sulfate): Iscover (Bristol-Myers Squibb), Plavix (Sanofi, Sanofi Winthrop, Sanofi Pharma Bristol-Myers Squibb SNC).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl clopidogrel bisulfate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Clopidogrel bisulfate/
【Specification】

? Clopidogrel (CAS NO.113665-84-2), its Synonyms are ( )-(S)-Clopidogrel ; (S)-Clopidogrel ; Clopidogrel 1A Pharma ; Clopidogrel Acino ; Clopidogrel BMS ; Clopidogrel Hexal ; Clopidogrel Teva (hydrogen sulphate) ; Clopidogrel Winthrop ; Clopidogrel ratiopharm GmbH ; HSDB 7430 ; Iscover ; Plavix ; Methyl (+)-(S)-alpha-(o-chlorophenyl)-6,7-dihydrothieno(3,2-c)pyridine-5(4H)-acetate ; Thieno(3,2-c)pyridine-5(4H)-acetic acid, alpha-(2-chlorophenyl)-6,7-dihydro-, methyl ester, (S)- .

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Prepn: (unspec. stereochem.): D. Aubert et al., EP 99802; eidem, US patent 4529596 (1984, 1985 both to Sanofi). Prepn of (+)-form: A. Badorc, D. Frehel, EP 281459; eidem, US patent 4847265 (1988, 1989 both to Sanofi).
... Prepared by condensing 4,5,6,7-tetrahydrothienol[3,2-c]pyridine with racemic methyl -chloro-(2-chlorophenyl)acetate in the presence of potassium carbonate and optical resolution of the product obtained

Biomedical Effects and Toxicity

【Pharmacological Action】
- Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
- Compounds that bind to and block the stimulation of PURINERGIC P2Y RECEPTORS. Included under this heading are antagonists for specific P2Y receptor subtypes.
【Therapeutic Uses】
Platelet Aggregation Inhibitors
MEDICATION: Antithrombotic
Clopidogrel is indicated for reducing the risk of atherosclerotic events (myocardial infarction, stroke, and vascular death) in patients with atherosclerosis documented by recent myocardial infarction, recent stroke, or established peripheral arterial disease. /Included in US product labeling/
【Biomedical Effects and Toxicity】
Protein binding: Very high, for clopidogrel and its main circulating metabolite (98% and 94%, respectively). Binding is nonsaturable in vitro up to a concentration of 100 ug/mL.
Absorption: Rapid, at least 50%. Bioavailability has not been found to be affected by food.
Time to peak effect: Steady sate inhibition of platelet aggregation with repeated doses of 75 mg/day usually occurs between day 3 and day 7.
Peak plasma concentration: Approximately 3 mg/L (carboxylic acid derivative) after repeated doses of 75 mg. Pharmacokinetics of the main circulating metabolite are linear (increased in proportion to dose) in a dose range of 50 to 150 mg.
Time to peak concentration: Plasma: Approximately 1 hour for the carboxylic acid derivative.
Elimination: Renal, approximately 50%, five days after dosing with radiolabeled clopidogrel. Fecal, approximately 46%, five days after dosing with radiolabeled clopidogrel.
It is not known whether clopidogrel is distributed into human breast milk. Clopidogrel and/or its metabolites are distributed into the milk of lactating rats.

Supplier Location

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