Clopidogrel bisulfate

Base Information

• Chemical Name: Clopidogrel bisulfate
• CAS No.: 120202-66-6
• Molecular Formula: C16H18ClNO6S2
• Molecular Weight: 419.907
• Hs Code.: 29349990
• European Community (EC) Number: 601-679-1,686-767-8
• NSC Number: 758613
• UNII: 08I79HTP27
• DSSTox Substance ID: DTXSID601016080
• Wikidata: Q27888063
• NCI Thesaurus Code: C2673
• RXCUI: 236991
• ChEMBL ID: CHEMBL1083385
• Mol file: 120202-66-6.mol

Synonyms:clopidogrel;clopidogrel besilate;clopidogrel besylate;clopidogrel bisulfate;clopidogrel hydrochloride;Clopidogrel Mepha;clopidogrel napadisilate;clopidogrel Sandoz;clopidogrel, (+)(S)-isomer;clopidogrel-Mepha;Iscover;PCR 4099;PCR-4099;Plavix;SC 25989C;SC 25990C;SR 25989

Chemical Property of Clopidogrel bisulfate

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 8.71E-09mmHg at 25°C
• Melting Point: 184oC
• Boiling Point: 423.7 °C at 760 mmHg
• Flash Point: 210 °C
• PSA: 140.76000
• LogP: 3.96550
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ~26 mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 419.0264073
• Heavy Atom Count: 26
• Complexity: 463

Purity/Quality:

99.5% ^*data from raw suppliers

(S)-(+)-Clopidogrel hydrogensulfate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O
• Isomeric SMILES: COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O
• Recent ClinicalTrials: A Study to Evaluate the Efficacy and Safety of Renexin CR in Patients With Acute Non-cardioembolic Ischemic Stroke
• Recent EU Clinical Trials: Genotype-gUIded cLopidogrel monoTherapY (POPular GUILTY)
• Recent NIPH Clinical Trials: Control of steroid-associated osteonecrosis of the femoral head in SLE patients
• 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.
• 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. Used as an antithrombotic. An irreversible inhibitor of P2Y12.
• Therapeutic Function: Platelet aggregation inhibitor

Technology Process of Clopidogrel bisulfate

There total 59 articles about Clopidogrel bisulfate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride (141109-18-4,141109-19-5) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → (S)-(+)-clopidogrel bisulfate (120202-66-6,120202-71-3,144077-07-6)

Guidance literature:

(S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride; formaldehyd; In methanol; at 43 ℃; for 5h;

With sulfuric acid; at 38 ℃; for 4h; Temperature;

Reference yield: 96.2%

methyl (S)-2-(2-chlorophenyl)-2-[2-(thien-2-yl)ethylamino]acetate (141109-20-8) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → (S)-(+)-clopidogrel bisulfate (120202-66-6,120202-71-3,144077-07-6)

Guidance literature:

methyl (S)-2-(2-chlorophenyl)-2-[2-(thien-2-yl)ethylamino]acetate; formaldehyd; With sulfuric acid; In chloroform; at 20 ℃;

With sulfuric acid; In acetone; at 10 ℃; for 2h; Solvent; Temperature;

Reference yield: 95.2%

methyl (R)-2-(2-chlorophenyl)-2-benzenesulfonyloxyacetate (223123-46-4) + 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride (28783-41-7) → (S)-(+)-clopidogrel bisulfate (120202-66-6,120202-71-3,144077-07-6)

Guidance literature:

methyl (R)-2-(2-chlorophenyl)-2-benzenesulfonyloxyacetate; 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride; With sodium hydrogencarbonate; In acetone; for 6h; Reflux;

With sulfuric acid; In acetone;

upstream raw materials:

(S)-(+)-clopidogrel

clopidogrel

clopidogrel hydrogen sulfate

methyl (R)-2-(2-chlorophenyl)-2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)acetate

Downstream raw materials:

clopidogrel hydrogen sulfate

SR 26334

clopidogrel besylate

(S)-methyl 2-(2-bromo-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(2-chlorophenyl)acetate

Refernces

• 1、 Kumar, K. Naveen,Mhate, Mouzma,Panchami, Hirave,Ravichandiran, V.,Swain, Sharada Prasanna. "Copper (II) bromide catalysed one pot bromination and amination for the green, cost-effective synthesis of clopidogrel". . . Retrieved 2022/03/15.
• 2、 -. "Preparation method of clopidogrel hydrogen sulfate intermediate". . . Retrieved 2021/05/15.