Ramosetron hydrochloride

Base Information

• Chemical Name: Ramosetron hydrochloride
• CAS No.: 132907-72-3
• Molecular Formula: C17H18ClN3O
• Molecular Weight: 315.802
• Hs Code.: 2933990090
• European Community (EC) Number: 690-014-9
• UNII: 9551LHD87E
• DSSTox Substance ID: DTXSID3021223
• Wikidata: Q27271742
• NCI Thesaurus Code: C88299
• ChEMBL ID: CHEMBL3181841
• Mol file: 132907-72-3.mol

Synonyms:5-((1-methyl-3-indolyl)carbonyl)-4,5,6,7-tetrahydro-1H-benzimidazol;Methanone, (1-methyl-1H-indol-3-yl)(4,5,6,7-tetrahydro-1H-benzimidazol-5-yl)-, monohydrochloride, (R)-;Nasea;ramosetron;ramosetron hydrochloride;YM 060;YM-060;YM060

Chemical Property of Ramosetron hydrochloride

Chemical Property:

• Vapor Pressure: 1.96E-13mmHg at 25°C
• Melting Point: 244-246°C
• Boiling Point: 579.7 °C at 760 mmHg
• Flash Point: 304.4 °C
• PSA: 50.68000
• LogP: 3.69120
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: H2O: soluble20mg/mL, clear
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 315.1138399
• Heavy Atom Count: 22
• Complexity: 413

Purity/Quality:

99% ^*data from raw suppliers

Ramosetron hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C2=CC=CC=C21)C(=O)C3CCC4=C(C3)NC=N4.Cl
• Isomeric SMILES: CN1C=C(C2=CC=CC=C21)C(=O)[C@@H]3CCC4=C(C3)NC=N4.Cl
• Recent ClinicalTrials: Ramosetron on Late PONV (Postoperative Nausea and Vomiting)
• Recent EU Clinical Trials: A RANDOMIZED, DOUBLE-BLIND, PLACEBO-CONTROLLED STUDY TO INVESTIGATE THE POTENTIAL EFFICACY, SAFETY AND TOLERABILITY OF DIFFERENT ORAL DOSES OF YM060 IN PATIENTS WITH DIARRHEA-PREDOMINANT IRRITABLE BOWEL SYNDROME
• Recent NIPH Clinical Trials: Efficacy of ramosetron hydrochloride in male patients with diarrhea-predominant irritable bowel syndrome
• Description: Ramosetron Hydrochloride is the only currently available drug indicated for the treatment of male patients with IBS-D in Japan. Ramosetron Hydrochloride was approved in July 1996 under a brand name of Nasea Injection 0.3 mg and in June 1998 under a brand name of Nasea OD tablets 0.1 mg for the treatment of gastrointestinal symptoms (nausea and vomiting) associated with therapy with antineoplastic drugs (e.g., cisplatin).Nasea was launched in Japan for chemotherapy-induced emesis. Nasea was prepared by a four step sequence via the Vilsmeier-type coupling of 1-methylindole and 5-( 1- pyrrolidoncarbonyl)-4,5,6,7-tetrahydro-Hl-benzimidazole hydrochloride. The antiemetic activity arises because it is a potent 5-HT3 receptor antagonist that is i.v. and orally active. The (R)-isomer was found to be 100 times more potent than the (S)-isomer. It was able to inhibit cisplatin-induce emesis and was 8670 times more potent than netoclopramide.
• Uses: Ramosetron Hydrochloride is a selective serotonin 5-HT3 receptor antagonist and has structurally different from Ondansetron (O655000), Granisetron (G780000). It controls excessive bowel movement and diarrhea by inhibiting 5-HT3 receptors in the intestinal tract. Ramosetron Hydrochloride was approved as film-coated tablets in July 2008 and as orally disintegrating tablets in August 2013 for the indication of treatment of male patients with diarrhea-predominant irritable bowel syndrome.

Technology Process of Ramosetron hydrochloride

There total 2 articles about Ramosetron hydrochloride 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:

(R)-5-[(1-methyl-3-indolyl)carbonyl]-4,5,6,7-tetrahydro-1H-benzimidazole (132036-39-6) → ramosetron hydrochloride (132907-72-3)

Guidance literature:

DOI:10.1248/cpb.44.1707

Reference yield:

ramosetron (132036-88-5) → 5-[(1-methyl-1H-indole-6-yl)carbonyl]-4,5,6,7-tetrahydro-1H-benzimidazole (912850-42-1) + 5-[(1-methyl-1H-indole-5-yl)carbonyl]-4,5,6,7-tetrahydro-1H-benzimidazole (912850-41-0) + ramosetron hydrochloride (132907-72-3)

Guidance literature:

With hydrogenchloride; In ethanol; ethyl acetate; at 70 ℃; for 1 - 12h; Product distribution / selectivity;

upstream raw materials:

(R)-5-[(1-methyl-3-indolyl)carbonyl]-4,5,6,7-tetrahydro-1H-benzimidazole

ramosetron

Refernces

• 1、 -. "NOVEL PROCESS FOR PRODUCING RAMOSETRON OR ITS SALT". Page/Page column 10-11. . Retrieved 2008/06/13.