Ticlopidine

Base Information

• Chemical Name: Ticlopidine
• CAS No.: 55142-85-3
• Molecular Formula: C14H14 Cl N S
• Molecular Weight: 263.791
• Hs Code.: 2934999090
• European Community (EC) Number: 259-498-5
• UNII: OM90ZUW7M1
• DSSTox Substance ID: DTXSID5023669
• Nikkaji Number: J11.390E
• Wikipedia: Ticlopidine
• Wikidata: Q420571
• NCI Thesaurus Code: C61972
• Pharos Ligand ID: DJTFBY3F8FKR
• Metabolomics Workbench ID: 42612
• ChEMBL ID: CHEMBL833
• Mol file: 55142-85-3.mol

Synonyms:53 32C;53-32C;5332C;Hydrochloride, Ticlopidine;Ticlid;Ticlodix;Ticlodone;Ticlopidine;Ticlopidine Hydrochloride

Chemical Property of Ticlopidine

Chemical Property:

• Melting Point: 210-212 °C
• Boiling Point: 117-120 °C(Press: 0.5 Torr)
• PKA: 7.10±0.20(Predicted)
• PSA: 31.48000
• Density: 1.273±0.06 g/cm3(Predicted)
• LogP: 3.89770
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 263.0535483
• Heavy Atom Count: 17
• Complexity: 261

Purity/Quality:

99%, ^*data from raw suppliers

Ticlopidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antithrombotic Agents
• Canonical SMILES: C1CN(CC2=C1SC=C2)CC3=CC=CC=C3Cl
• Recent ClinicalTrials: A Study to Assess the Effect of Ticlopidine on the Pharmacokinetics, Safety, and Tolerability of Intranasally Administered Esketamine in Healthy Participants
• Recent EU Clinical Trials: Anti-Thrombotic Strategy to Lower All Cardiovascular and Neurologic Ischemic and Hemorrhagic Events after Trans-Aortic Valve Implantation for Aortic Stenosis: The ATLANTIS trial
• Recent NIPH Clinical Trials: Binary investigation on the Effects of antiplatelet agents post-PCI: the Necessity of considering vascular Endothelial Function in post coronary Intervention pharmacotherapy
• Uses: Ticlopidine suppresses aggregation of thrombocytes and possesses antiaggregant activity. It is believed that its action is connected to its effect on thrombocyte membranes and the reduction in quantity of released adenosine diphosphate and serotonin, which facilitate aggregation of thrombocytes. In wide-ranging clinical trials, ticlopidine presented a number of advantages compared to aspirin. Ticlopidine is an antiplatelet drug for the treatment of ischemic heart diseases.
• Therapeutic Function: Platelet aggregation inhibitor

Technology Process of Ticlopidine

There total 16 articles about Ticlopidine 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: 95.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (54903-50-3) + 2-bromo-1-chlorobenzene (694-80-4) → ticlopidine (55142-85-3)

Guidance literature:

2-bromo-1-chlorobenzene; With ethylene dibromide; trifluoroacetic acid; cobalt(II) bromide; zinc; In acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;

formaldehyd; 4,5,6,7-tetrahydrothieno[3,2-c]pyridine; In acetonitrile; at 60 ℃; for 1h; Inert atmosphere;

DOI:10.3390/molecules15118144

Reference yield: 90.0%

→ ticlopidine (55142-85-3) + (E)-2-(thiophen-2-yl)acetaldehyde oxime

Guidance literature:

Reference yield: 78.0%

2-(2-bromoethyl)-3-(bromomethyl)thiophene (865187-82-2) + 2-CHLOROBENZYLAMINE (89-97-4) → ticlopidine (55142-85-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 5 ℃; for 5h; Heating / reflux;

upstream raw materials:

4,5,6,7-tetrahydrothieno[3,2-c]pyridine

1-chloro-2-(chloromethyl)benzene

5-(2-chloro-benzyl)-5,6-dihydro-4H-thieno[3,2-c]pyridin-7-one; hydrochloride

3-Bromomethylthiophene

Downstream raw materials:

1-[5-(2-Chloro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-2-yl]-butan-1-one

[4-(3-Chloro-propoxy)-phenyl]-(2-ethyl-thieno[3,2-c]pyridin-3-yl)-methanone

[4-(3-Bromo-propoxy)-phenyl]-(2-ethyl-thieno[3,2-c]pyridin-3-yl)-methanone

(2-Butyl-thieno[3,2-c]pyridin-3-yl)-(4-methoxy-phenyl)-methanone

Refernces

• 1、 Isabelle, Aillaud,Haurena, Caroline,Gall, Erwan Le,Martens, Thierry,Ricci, Gino. "2-Chlorophenyl zinc bromide: A convenient nucleophile for the mannich-related multicomponent synthesis of clopidogrel and ticlopidine". experimental part. p. 8144 - 8155. Retrieved 2011/02/27.
• 2、 -. "MEDICINAL COMPOSITION". . . Retrieved 2008/06/13.