Tropisetron

Base Information

• Chemical Name: Tropisetron
• CAS No.: 89565-68-4
• Molecular Formula: C₁₇H₂₀N₂O₂
• Molecular Weight: 284.358
• UNII: 6I819NIK1W
• DSSTox Substance ID: DTXSID2044137
• Nikkaji Number: J1.639.709A,J22.211I
• Wikipedia: Tropisetron
• Wikidata: Q29428,Q27166461
• NCI Thesaurus Code: C1131
• Pharos Ligand ID: Z1HG9Z9KH76A
• ChEMBL ID: CHEMBL56564,CHEMBL1289230
• Mol file: 89565-68-4.mol

Synonyms:(3 alpha-tropanyl)-1H-indole-3-carboxylic acid ester;ICS 205 930;ICS 205-930;ICS 205930;ICS-205-930;ICS-205930;Indole 3 carboxylic Acid Tropine Ester;indole-3-carboxylic acid tropine ester;Navoban;tropisetron;tropisetron hydrochloride

Chemical Property of Tropisetron

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 201-202 °C
• Refractive Index: 1.644
• Boiling Point: 448.5 °C at 760 mmHg
• PKA: 15.38±0.30(Predicted)
• Flash Point: 225 °C
• PSA: 83.80000
• Density: 1.26 g/cm³
• LogP: 4.38640
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 284.152477885
• Heavy Atom Count: 21
• Complexity: 400

Purity/Quality:

99% ^*data from raw suppliers

Tropisetron 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C2CCC1CC(C2)OC(=O)C3=CNC4=CC=CC=C43
• Isomeric SMILES: CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)C3=CNC4=CC=CC=C43
• Recent ClinicalTrials: Efficacy of Three Antiemetics in Preventing Nausea and Vomiting
• Recent EU Clinical Trials: Etude comparative de l'influence de deux antagonistes du récepteur 5-HT3, le tropisétron et le granisétron, sur l'effet analgésique du paracétamol.
• Recent NIPH Clinical Trials: Double-blind placebo controlled study of the adjunctive effect of tropisetron on cognitive deficits in schizophrenia
• Description: Tropisetron is the third selective 5HT3-antagonist, after ondansetron and granisetron, to be introduced for the management of nausea and vomiting induced by cancer chemotherapy. Similar to the other two 5HT3-antagonists, vopisetron is superior to metoclopramide. The compound has also been reported to have antiarrhythmic activity.
• Uses: A substance that is used to prevent nausea and vomiting caused by chemotherapy.

Technology Process of Tropisetron

There total 3 articles about Tropisetron 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: 80.0%

Indole-3-carbonyl chloride (59496-25-2) + 3-tropanol (120-29-6) → tropisetron (89565-68-4,89565-86-6,124583-47-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 60 - 65 ℃; for 20h;

Reference yield:

1H-indole-3-carboxylic acid (771-50-6) → tropisetron (89565-68-4,89565-86-6,124583-47-7)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / dichloromethane / 2 h / 0 - 20 °C

2: triethylamine / tetrahydrofuran / 20 h / 60 - 65 °C

With thionyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;

Reference yield:

→ tropisetron (89565-68-4,89565-86-6,124583-47-7)

Guidance literature:

upstream raw materials:

Indole-3-carbonyl chloride

3-tropanol

1H-indole-3-carboxylic acid

Refernces

• 1、 -. "USE OF ONDANSETRON IN THE MANUFACTURE OF A MEDICAMENT FOR THE TREATMENT OF TREMOR". . . Retrieved 2008/06/13.