Clopidogrel Bisulfate Property

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

BCS Class

2

InChIKey

FDEODCTUSIWGLK-RSAXXLAASA-N

CAS DataBase Reference

120202-66-6(CAS DataBase Reference)

Safety

Safety Statements 

22-24/25

RIDADR 

1759

WGK Germany 

3

HazardClass 

8

PackingGroup 

II

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

H335May cause respiratory irritation

H362May cause harm to breast-fed children

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P263Avoid contact during pregnancy/while nursing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P310Immediately call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P363Wash contaminated clothing before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

Clopidogrel Bisulfate Chemical Properties,Usage,Production

Description

(S)-(+)-Clopidogrel is the functional enantiomer of clopidogrel and a prodrug whose thiol metabolite antagonizes purine binding to the platelet purinergic receptor P2Y₁₂ (K_i = 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

Used as an antithrombotic.

Uses

An irreversible inhibitor of P2Y12.

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.

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%) 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 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.

storage

Store at RT