120202-66-6 Usage
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
Different sources of media describe the Uses of 120202-66-6 differently. You can refer to the following data:
1. Clopidogrel Bisulfate is an oral, thienopyridine class antiplatelet agent used to inhibit blood clots in coronary artery disease, peripheral vascular disease, and cerebrovascular disease.
2. Used as an antithrombotic.
3. An irreversible inhibitor of P2Y12.
Manufacturing Process
Levo-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%) areadded 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 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 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.
Check Digit Verification of cas no
The CAS Registry Mumber 120202-66-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,0,2,0 and 2 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 120202-66:
(8*1)+(7*2)+(6*0)+(5*2)+(4*0)+(3*2)+(2*6)+(1*6)=56
56 % 10 = 6
So 120202-66-6 is a valid CAS Registry Number.
InChI:InChI=1/C15H14ClNO2S.H2O4S/c16-12-4-2-1-3-11(12)14(15(18)19)17-7-5-13-10(9-17)6-8-20-13;1-5(2,3)4/h1-4,6,8,14H,5,7,9H2,(H,18,19);(H2,1,2,3,4)/t14-;/m0./s1
120202-66-6Relevant articles and documents
Efficient Synthesis of (S)-(+)-Clopidogrel Bisulfate-Capped Silver Nanoparticles
Mahmoodi, Nosrat O.,Ghavidast, Atefeh,Ashkan, Mitra,Mamaghani, Manouchehr,Zanjanchi, Mohammad Ali,Tabatabaeian, Khalil,Arabanian, Armin
, p. 1552 - 1557 (2016)
In this work primarily one-pot synthetic development in the preparation of clopidogrel bisulfate with a polymorphic crystalline form II in 90% yield was developed. This premade antiplatelet drug has been used to protect starch-stabilized silver nanoparticles (AgNPs).
Preparation method of clopidogrel hydrogen sulfate and intermediate N-(2-thiopheneethyl) methyleneimine of clopidogrel hydrogen sulfate
-
, (2021/05/08)
The invention discloses a preparation method of clopidogrel hydrogen sulfate and an intermediate N-(2-thiophene ethyl) methyleneamine of the clopidogrel hydrogen sulfate. The synthesis method of the intermediate comprises the step of carrying out an Eschweiler-Clarke methylation reaction by taking 2-thiophene ethylamine and paraformaldehyde as raw materials to obtain the N-(2-thiophene ethyl) methyleneamine. The invention also provides a method for preparing clopidogrel hydrogen sulfate. According to the synthesis method provided by the invention, the required solid product (N-(2-thiopheneethyl) methyleneimine) is synthesized in one step, the synthesis method is simple, the qualified solid compound is directly obtained, the time and the raw material cost are saved, the storage and the transportation are convenient, the purity is good, the yield is high, and the synthesis method is suitable for industrial production.
Preparation method of clopidogrel hydrogen sulfate
-
, (2021/02/10)
The invention relates to a preparation method of clopidogrel hydrogen sulfate. The preparation method comprises the following steps: reacting (S)-o-chlorophenylglycine methyl ester with 1, 1, 1, 3, 3,3-hexamethyldisilazane to obtain trimethylsilyl protected (S)-o-chlorophenylglycine methyl ester; in the presence of acetonitrile, superfine powder potassium carbonate and the trimethylsilyl protected (S)-o-chlorophenylglycine methyl ester, adding 2- (2-bromoethyl) thiophene, evaporating acetonitrile in batches, adding water and methyl acetate, extracting to obtain a methyl acetate solution of (S)-2-thiophene ethylamino-2-chlorophenylmethyl acetate, dropwise adding concentrated hydrochloric acid, carrying out pulping and cooling to obtain (S)-2-thiophene ethylamino methyl-2-chlorophenyl acetate hydrochloride, mixing the (S)-2-thiophene ethylamino methyl-2-chlorophenyl acetate hydrochloride with a formaldehyde aqueous solution for reaction, and carrying out reaction with concentrated sulfuric acid to obtain the clopidogrel hydrogen sulfate. According to the method, the high-purity (S)- 2-thiophene ethylamino-2-chlorophenyl methyl acetate hydrochloride and clopidogrel hydrogen sulfate can be obtained with high efficiency and high yield, and the method is suitable for industrial production.
