Clopidogrel Bisulfate CAS 120202-66-6
Introduction：Basic information about Clopidogrel Bisulfate CAS 120202-66-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Clopidogrel Bisulfate Basic information
| Product Name: | Clopidogrel Bisulfate |
| Synonyms: | Clopidogrel (Plavix);CLOPIDOGREL SULFATE;CLOPIDOGREL SULPHATE;CLOPIDOGREL HYDROGEN SULPHATE;CLOPIDOGREL BISULPHATE;CLOPIDOGREL BISULFATE;Myogrel;Stroka |
| CAS: | 120202-66-6 |
| MF: | C16H16ClNO2S.H2O4S |
| MW: | 419.9 |
| EINECS: | 1806241-263-5 |
| Product Categories: | APIs;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Clopidogrel;INTERMEDIATES OF CLOPIDOGREL;Iscover;Cardiovascular APIs;Pharmaceutical intermediates;Cardiovascular Series;API;120202-66-6 |
| Mol File: | 120202-66-6.mol |
Clopidogrel Bisulfate Chemical Properties
| Melting point | 174-176°C |
| storage temp. | 2-8°C |
| solubility | DMSO: ~26 mg/mL |
| form | solid |
| color | white |
| Optical Rotation | [α]/D +54 to +70°, c = 0.5 in methanol |
| BRN | 9967887 |
| BCS Class | 2 |
| Major Application | pharmaceutical (small molecule) |
| InChI | InChI=1/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-;/s3 |
| InChIKey | FDEODCTUSIWGLK-RSAXXLAASA-N |
| SMILES | S(O)(O)(=O)=O.[C@@H](C1C=CC=CC=1Cl)(N1CCC2SC=CC=2C1)C(=O)OC |&1:5,r| |
| CAS DataBase Reference | 120202-66-6(CAS DataBase Reference) |
Safety Information
| Safety Statements | 22-24/25 |
| RIDADR | 1759 |
| WGK Germany | 3 |
| HazardClass | 8 |
| PackingGroup | II |
| HS Code | 29349990 |
| Storage Class | 8A - Combustible corrosive hazardous materials |
| Hazard Classifications | Aquatic Chronic 2 Eye Dam. 1 Skin Corr. 1B |
| Description | (S)-(+)-Clopidogrel is the functional enantiomer of clopidogrel and a prodrug whose thiol metabolite antagonizes purine binding to the platelet purinergic receptor P2Y12 (Ki = 316 nM in human platelets). It is metabolized by the cytochrome P450 (CYP) isoform CYP2C19 in rat liver and inhibits ADP-induced platelet aggregation ex vivo. Formulations containing (S)-(+)-clopidogrel have been used in combination with aspirin to prevent vascular ischemic events in patients with acute coronary syndromes. |
| Chemical Properties | Off-White Solid |
| Originator | Iscover,Bristol-Myers |
| Uses | Clopidogrel Bisulfate is an oral, thienopyridine class antiplatelet agent used to inhibit blood clots in coronary artery disease, peripheral vascular disease, and cerebrovascular disease. |
| Uses | Used as an antithrombotic. |
| Uses | An irreversible inhibitor of P2Y12. |
| Manufacturing Process | Levo-rotatory ammonium camphor-10-sulfonate is dissolved in a minimum ofwater and applied to the column of Amberlite IRN-77 resin. Elution is carriedout with water. The eluted fractions containing the levo-rotatory camphor-10-sulfonic acid are lyophilized, melting point 198°C. 32 g (0.0994 mole) of racemic methyl-α-5-(4,5,6,7-tetrahydro-thieno(3,2-c)pyridyl)(2-chlorophenyl)-acetate are dissolved in 150 ml of acetone. 9.95 g(0.0397 mole) of levo-rotatory camphor-10-sulfonic acid monohydrate areadded. The clear solution is left to stand at room temperature. After 48 hoursthe reaction mixture is concentrated to 50 ml and left to stand at roomtemperature for 24 hours. The obtained camphor-10-sulfonic acid salt ofmethyl-α-5-(4,5,6,7-tetrahydro-thieno(3,2-c)pyridyl)(2-chlorophenyl)-acetate(SR 25990) are filtered off, washed with acetone and dried (yield: 55% on thebasis of the starting racemate), melting point 165°C, [α]D20=+24.67 (c=1.58g/100 ml; methanol). The crystals obtained above are redissolved in theminimum of boiling acetone (50 ml). The crystals obtained after cooling arefiltered off, washed with acetone and dried (yield: 88%), m.p. 165°C,[α]D20=+24.75 (c=1.68 g/100 ml; methanol). 12 g (0.022 mole) of the pure camphor-10-sulfonic acid salt of methyl-α-5-(4,5,6,7-tetrahydro-thieno(3,2-c)pyridyl)(2-chlorophenyl)-acetate aredissolved in a minimum of water. After cooling to 5°C, the aqueous solutionobtained is made alkaline with a saturated aqueous solution of sodiumhydrogen carbonate. The alkaline aqueous phase is extracted withdichloromethane. The organic extracts are dried over anhydrous sodiumsulfate. On evaporation of the solvent a colorless oil of dextro-rotatorymethyl-α-5-(4,5,6,7-tetrahydro-thieno(3,2-c)pyridyl)(2-chlorophenyl)-acetateis obtained (quantitative yield). Oil, [α]D20=+51.52 (c=1.61 g/100 ml;methanol). 800 ml of a saturated aqueous solution of sodium bicarbonate are added to asuspension of 200 g of SR 25990 in 800 ml of dichloromethane. After vigorousshaking, the organic phase is separated, dried over sodium sulfate and thesolvent is removed under reduced pressure. The residue is dissolved in 500 mlof ice-cold acetone and 20.7 ml of concentrated sulfuric acid (93.64%) are added drop-wise. The precipitate formed is isolated by filtration and washedwith 1 L of acetone, then dried in a vacuum oven at 50°C. 139 g of purewhite crystals of hydrogen sulfate of dextro-rotatory methyl-α-5-(4,5,6,7-tetrahydro-thieno(3,2-c)pyridyl)(2-chlorophenyl)-acetate (SR 25990 C) arethus obtained, m.p. 184°C, [α]D20=+55.10 (c=1.891 g/100 ml; methanol). |
| Brand name | Plavix (Sanofi Aventis). |
| Therapeutic Function | Platelet aggregation inhibitor |
| General Description | Clopidogrel bisulfate (CLP) is an antiplatelet drug, which belongs to the thienopyridine class of drug. |
| Biochem/physiol Actions | (S)-(+)-Clopidogrel hydrogen sulfate is an antithrombotic antiplatelet agent. It specifically and irreversibly inhibits the Purinoceptor P2Y12 subtype which inhibits ADP-induced platelet aggregation. (S)-(+)-Clopidogrel hydrogen sulfate is the active isomer. |
| Veterinary Drugs and Treatments | Clopidogrel, a platelet aggregation inhibitor, may be useful for preventingthrombi in susceptible cats. It may also improve pelvic limbcirculation in cats after a cardiogenic embolic event via a vasomodulatingeffect secondary to inhibition of serotonin release from platelets.Research is ongoing. |
| storage | Store at RT |
| References | [1] J. M. HERBERT. Clopidogrel, A Novel Antiplatelet and Antithrombotic Agent[J]. Cardiovascular Therapeutics, 1993, 11 2: 180-198. DOI: 10.1111/j.1527-3466.1993.tb00275.x |
Clopidogrel Bisulfate Preparation Products And Raw materials
| Raw materials | (-)-CAMPHOR-10-SULFONIC ACID AMMONIUM SALT-->4,5,6,7-Tetrahydrothieno[3,2,c] pyridine hydrochloride-->Sulfuric acid-->Methyl 4-chlorophenylacetate |
