Clopidogrel

Base Information

• Chemical Name: Clopidogrel
• CAS No.: 113665-84-2
• Molecular Formula: C16H16ClNO2S
• Molecular Weight: 321.828
• European Community (EC) Number: 601-269-2
• NSC Number: 748298
• UNII: A74586SNO7
• DSSTox Substance ID: DTXSID6022848
• Nikkaji Number: J691.232J
• Wikipedia: Clopidogrel
• Wikidata: Q410237
• NCI Thesaurus Code: C61686
• RXCUI: 32968
• Pharos Ligand ID: A2KHQ3U645YJ
• Metabolomics Workbench ID: 38700
• ChEMBL ID: CHEMBL1771
• Mol file: 113665-84-2.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

Chemical Property:

• Appearance/Colour: white powder
• Boiling Point: 423.7 °C at 760 mmHg
• PKA: 4.56±0.20(Predicted)
• Flash Point: 210 °C
• PSA: 57.78000
• Density: 1.317 g/cm³
• LogP: 3.61180
• Storage Temp.: 2-8°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 321.0590276
• Heavy Atom Count: 21
• Complexity: 381

Purity/Quality:

98%min ^*data from raw suppliers

Clopidogrel-13C-d4HCl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antithrombotic Agents
• Canonical SMILES: COC(=O)C(C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3
• Isomeric SMILES: COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3
• Recent ClinicalTrials: Effect of Clopidogrel on Allergen Challenge in Asthma
• Recent EU Clinical Trials: Genotype-gUIded cLopidogrel monoTherapY (POPular GUILTY)
• Recent NIPH Clinical Trials: ShorT and OPtimal duration of Dual AntiPlatelet Therapy-3 study
• Description: Clopidogrel was launched in the US as a potent inhibitor of platelet aggregation for the preventive management of secondary ischemic events, including MI, stroke and vascular deaths. Clopidogrel can be synthesized in 4 steps (including an optical resolution to the S active enantiomer) from 2-(2- ch1orophenyl)-glycine, the key step being the cyclization to thienopyridine with formaldehyde and acetic acid. Clopidogrel belongs to the original chemical class of Ticlopidine, but shows fewer side effects (in particular, bone-marrowsuppressing effects) at the dosage generally used. Like Ticlopidine, it is an Adenosine diphosphate (ADP) antagonist acting at the purinergic P2y receptor. In in vivo experiments with rabbits, Clopidogrel shows a maximal antiaggregant effect at 20mg/kg po, reducing adhesion of platelets to the vascular subendothelium ; moreover, it reduces myointimal thickening occuring after endothelial injury of rat carotid artery. Clopigrel does not affect platelet aggregation in vitro ; actually, its in vivo activity is highly dependent on hepatic metabolism. The results of a CAPRIE trial (Clopidogrel versus Aspirin in patients at risk of ischemic events) demonstrated that Clopidogrel was well tolerated and more effective than aspirin.
• Uses: anthelmintic, antiparasitic, antimite Sertraline metabolite
• Clinical Use: Clopidogrel acts as an antagonistto the P2Y2 receptor. It is probably a prodrug that requiresmetabolic activation, because in vitro studies do not interferewith platelet aggregation. Although platelet aggregationis not normally seen in the first 8 to 11 days after administrationto a patient, the effect lasts for several days after thedrug therapy is discontinued. Unlike other thienopyridinescurrently used, clopidogrel does not seriously reduce thenumber of white cells in the blood, and therefore, routinemonitoring of the white blood cell count is not necessaryduring treatment.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: antiplatelet effect possibly reduced by erythromycin. Anticoagulants: enhanced anticoagulant effect with coumarins and phenindione; manufacturer advises to avoid with warfarin. Heparin: increased risk of bleeding. Antidepressants: antiplatelet effect possibly reduced by fluoxetine, fluvoxamine and moclobemide. Anti-diabetics: avoid with repaglinide if possible due to increased repaglinide exposure. Antiepileptics: antiplatelet effect possibly reduced by carbamazepine and oxcarbazepine. Antifungals: antiplatelet effect possibly reduced by fluconazole, itraconazole, ketoconazole and voriconazole. Antivirals: antiplatelet effect possibly reduced by etravirine. Statins: concentration of rosuvastatin increased, maximum rosuvastatin dose is 20 mg. Ulcer healing drugs: antiplatelet effect possibly reduced by cimetidine, lansoprazole, pantoprazole and rabeprazole; antiplatelet effect reduced by omeprazole and esomeprazole - avoid concomitant use if possible.

Technology Process of Clopidogrel

There total 96 articles about Clopidogrel 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)-(+)-clopidogrel bisulfate (120202-66-6,120202-71-3,144077-07-6) → (S)-(+)-clopidogrel (113665-84-2,94188-84-8)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; at 15 ℃; for 0.333333h;

Reference yield: 100.0%

clopidogrel camphorsulfonate (909279-85-2) → (S)-(+)-clopidogrel (113665-84-2,94188-84-8)

Guidance literature:

With sodium carbonate; In tert-butyl methyl ether; water; at 20 ℃; for 0.5h; Solvent;

Reference yield: 100.0%

clopidogrel camphorsulfonate → (S)-(+)-clopidogrel (113665-84-2,94188-84-8)

Guidance literature:

With sodium carbonate; In tert-butyl methyl ether; water; for 0.5h; Solvent;

upstream raw materials:

methyl (S)-2-(2-chlorophenyl)-2-[2-(thien-2-yl)ethylamino]acetate

formaldehyd

SR 26334

methyl iodide

Downstream raw materials:

(S)-(+)-2-(2-chlorophenyl)-2-(6,7-dihydrothieno-[3,2-c]pyridin-5(4H)-yl)acetic acid hydrochloride

(S)-clopidogrel bisulfate

clopidogrel

cis-5-thiol metabolite

Refernces

• 1、 Swain, Sharada Prasanna,Shri, Om,Ravichandiran. "Iridium and bis(4-nitrophenyl)phosphoric acid catalysed amination of diol by hydrogen-borrowing methodology for the synthesis of cyclic amine: Synthesis of clopidogrel". . . Retrieved 2021.
• 2、 Jung, Kiwon,Kim, Jae-Sun,Kim, Tae-Hyun,Kim, Jinwoong. "A facile solid-phase synthesis of (+)-(S)-clopidogrel". . p. 326 - 329. Retrieved 2013.
• 3、 -. "Preparation method of clopidogrel hydrogen sulfate and intermediate N-(2-thiopheneethyl) methyleneimine of clopidogrel hydrogen sulfate". Paragraph 0109; 0115. . Retrieved 2021/05/08.