Dolasetron mesylate

Base Information

• Chemical Name: Dolasetron mesylate
• CAS No.: 115956-13-3
• Molecular Formula: C20H24N2O6S
• Molecular Weight: 420.48
• European Community (EC) Number: 601-404-5,835-539-8
• NCI Thesaurus Code: C1153
• RXCUI: 29398
• ChEMBL ID: CHEMBL2368924
• Mol file: 115956-13-3.mol

Synonyms:1H-indole-3-carboxylic acid, (6R,9AS)-octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester, rel-, methanesulfonate, hydrate (1:1:1);1H-indole-3-carboxylic acid, octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester, (2-alpha,6-alpha,8-alpha,9a-beta)-;1H-indole-3-carboxylic acid-trans-octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester methanesulfonate;Anzemet;dolasetron;dolasetron mesilate monohydrate;dolasetron mesylate;dolasetron mesylate monohydrate;indole-3-carboxylic acid, ester with (8R)-hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one;MDL 73,147EF;MDL 73147EF;MDL-73147EF;octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl 1H-indole-3-carboxylate

Chemical Property of Dolasetron mesylate

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 1.65E-22mmHg at 25°C
• Melting Point: 278°
• Boiling Point: 674.6 °C at 760 mmHg
• Flash Point: 361.8 °C
• PSA: 134.38000
• LogP: 2.97740
• Storage Temp.: 2-8°C
• Solubility.: H2O: >30mg/mL
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 438.14607235
• Heavy Atom Count: 30
• Complexity: 627

Purity/Quality:

99% ^*data from raw suppliers

Dolasetron mesylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)O.C1C2CC3CC(CC1N3CC2=O)OC(=O)C4=CNC5=CC=CC=C54.O
• Isomeric SMILES: CS(=O)(=O)O.C1[C@@H]2CC(C[C@H]3N2CC(=O)C1C3)OC(=O)C4=CNC5=CC=CC=C54.O
• Recent ClinicalTrials: Real-time Decision Support for Postoperative Nausea and Vomiting (PONV) Prophylaxis
• Description: Dolasetron was launched as Anzemet in Australia and the US for the prevention of nausea and vomiting in chemotherapy patients. It is a highly potent and very selective antagonist of 5-HT3 receptors ; it is the sixth in this class of compounds to be marketed for the treatment of chemotherapy-induced emesis. The last two approved in this class were Nazasetron (1994) and Ramosetron (1996). Anzemet was prepared by a seven step sequence from a cyclopentenecarboxylic ester via a Robinson-Schopf cyclisation of a dialdehyde into a key 9-azabicyclo[3.3.l]nonan-3-one. In a clinical study with 164 cancer patients treated with Dolasetron mesylate prior to Cisplatin, single doses of 10- 50 mg achieved major control of nausea and emesis in 73% of subjects and were well tolerated. Results from pharmacokinetic studies in humans showed that the clinical effects and duration of action seem to be due mainly to a major plasma metabolite rapidly formed and very potent itself, the (+) enantiomeric alcohol obtained by enzymatic reduction of the cyclic ketone.
• Uses: Nausea in chemotherapy;5-HT3 antagonist Antidepressant Dolasetron Mesylate acts as a bridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist. Antiemetic.

Technology Process of Dolasetron mesylate

There total 11 articles about Dolasetron mesylate 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: 90.77%

methanesulfonic acid (75-75-2,98527-29-8) + endo-hexahydro-8-(3-indolylcarbonyloxy)-2,6-methano-2H-quinolizin-3(4H)-one (115956-12-2) → endo-hexahydro-8-(3-indolylcarbonyloxy)-2,6-methano-2H-quinolizin-3(4H)-one mesylate (115956-13-3)

Guidance literature:

In acetone; at 20 ℃; for 2.5h; Product distribution / selectivity;

Reference yield: 84.8%

methanesulfonic acid (75-75-2,98527-29-8) + dolasetron (115956-12-2) → dolasetron mesylate (115956-13-3)

Guidance literature:

In acetone; pH=2 - 3; Inert atmosphere; Reflux; Darkness;

Reference yield: 84.8%

methanesulfonic acid (75-75-2,98527-29-8) + dolasetron (115956-12-2) → dolasetron mesylate (115956-13-3)

Guidance literature:

In acetone; at 20 ℃; for 2h; pH=2 - 3; Darkness; Reflux;

upstream raw materials:

methanesulfonic acid

dolasetron

Indole-3-carbonyl chloride

endo-5-hydroxy-8-azatricyclo[5.3.1.0³,⁸]-undecan-10-one

Refernces

• 1、 -. "Dolasetron oxide and preparation method and application thereof". Paragraph 0092-0093; 0095. . Retrieved 2020/05/14.
• 2、 -. "Polymorphs of Dolasetron base and process for preparation thereof". Page/Page column 5. . Retrieved 2009/02/11.