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Clopidogrel Bisulfate

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Clopidogrel Bisulfate Basic information
Clopidogrel Bisulfate Chemical Properties
  • Melting point:174-176°C
  • storage temp. 2-8°C
  • solubility DMSO: ~26 mg/mL
  • form solid
  • color white
  • optical activity[α]/D +54 to +70°, c = 0.5 in methanol
  • BRN 9967887
  • InChIKeyFDEODCTUSIWGLK-RSAXXLAASA-N
  • CAS DataBase Reference120202-66-6(CAS DataBase Reference)
Safety Information
  • Safety Statements 22-24/25
  • RIDADR 1759
  • WGK Germany 3
  • HazardClass 8
  • PackingGroup II
  • HS Code 29349990
Clopidogrel Bisulfate Usage And Synthesis
  • Chemical PropertiesOff-White Solid
  • OriginatorIscover,Bristol-Myers
  • UsesClopidogrel Bisulfate is an oral, thienopyridine class antiplatelet agent used to inhibit blood clots in coronary artery disease, peripheral vascular disease, and cerebrovascular disease.
  • UsesUsed as an antithrombotic.
  • UsesAn irreversible inhibitor of P2Y12.
  • Manufacturing ProcessLevo-rotatory ammonium camphor-10-sulfonate is dissolved in a minimum of water and applied to the column of Amberlite IRN-77 resin. Elution is carried out 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 are added. The clear solution is left to stand at room temperature. After 48 hours the reaction mixture is concentrated to 50 ml and left to stand at room temperature for 24 hours. The obtained camphor-10-sulfonic acid salt of methyl-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 the basis of the starting racemate), melting point 165°C, [α]D20=+24.67 (c=1.58 g/100 ml; methanol). The crystals obtained above are redissolved in the minimum of boiling acetone (50 ml). The crystals obtained after cooling are filtered 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 are dissolved in a minimum of water. After cooling to 5°C, the aqueous solution obtained is made alkaline with a saturated aqueous solution of sodium hydrogen carbonate. The alkaline aqueous phase is extracted with dichloromethane. The organic extracts are dried over anhydrous sodium sulfate. On evaporation of the solvent a colorless oil of dextro-rotatory methyl-α-5-(4,5,6,7-tetrahydro-thieno(3,2-c)pyridyl)(2-chlorophenyl)-acetate is 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 a suspension of 200 g of SR 25990 in 800 ml of dichloromethane. After vigorous shaking, the organic phase is separated, dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is dissolved in 500 ml of 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 washed with 1 L of acetone, then dried in a vacuum oven at 50°C. 139 g of pure white 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) are thus obtained, m.p. 184°C, [α]D20=+55.10 (c=1.891 g/100 ml; methanol).
  • brand namePlavix (Sanofi Aventis).
  • Therapeutic FunctionPlatelet aggregation inhibitor
  • Veterinary Drugs and TreatmentsClopidogrel, a platelet aggregation inhibitor, may be useful for preventing thrombi in susceptible cats. It may also improve pelvic limb circulation in cats after a cardiogenic embolic event via a vasomodulating effect secondary to inhibition of serotonin release from platelets. Research is ongoing.
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