132907-72-3

Basic information

• Product Name: Ramosetron hydrochloride
• Synonyms: Methanone,(1-Methyl-1H-indol-3-yl)[(6R)-4,5,6,7-tetrahydro-1H-benziMidazol-6-yl]-,hydrochloride (1:1);(R)-5-[(1-Methyl-3-indolyl)carbonyl]-4,5,6,7-tetrahydro-1H-benzimidazole hydrochloride;(1-methylindol-3-yl)-[(5r)-4,5,6,7-tetrahydro-3h-benzimidazol-5-yl]methanone hydrochloride;RAMOSETRON HCL;RAMOSETRON HYDROCHLORIDE;(1-methyl-1h-indol-3-yl)(4,5,6,7-tetrahydro-1h-benzimidazol-5-yl)-methanon;(r)-5-((1-methyl-3-indolyl)carbonyl)-4,5,6,7-tetrahydro-1h-benzimidazolehydr;(r)-monohydrochlorid
• CAS NO: 132907-72-3
• Molecular Formula: C₁₇H₁₇N₃O*ClH
• Molecular Weight: 315.8
• Product Categories: Antiemetic;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API
• Mol File: 132907-72-3.mol

Chemical Properties

• Melting Point: 244-246°C
• Boiling Point: 579.7 °C at 760 mmHg
• Flash Point: 304.4 °C
• Appearance: white to beige/
• Vapor Pressure: 1.96E-13mmHg at 25°C
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: H2O: soluble20mg/mL, clear
• Stability: Hygroscopic
• CAS DataBase Reference: Ramosetron hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Ramosetron hydrochloride(132907-72-3)
• EPA Substance Registry System: Ramosetron hydrochloride(132907-72-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 132907-72-3(Hazardous Substances Data)

Usage

Uses

Used in Gastrointestinal Applications:
Ramosetron hydrochloride is used as an antiemetic agent for the treatment of gastrointestinal symptoms such as nausea and vomiting. Its application is particularly relevant in patients undergoing therapy with antineoplastic drugs, such as cisplatin, which are known to cause these symptoms.
Used in Diarrhea-Predominant Irritable Bowel Syndrome (IBS-D) Treatment:
Ramosetron hydrochloride is used as a therapeutic agent for the treatment of male patients with diarrhea-predominant irritable bowel syndrome (IBS-D) in Japan. It helps control excessive bowel movement and diarrhea by inhibiting 5-HT3 receptors in the intestinal tract.
Used in Chemotherapy-Induced Emesis:
Ramosetron hydrochloride is used as an antiemetic drug to prevent and treat nausea and vomiting induced by chemotherapy. Its high potency and effectiveness make it a preferred choice for managing chemotherapy-induced emesis.
Used in Pharmaceutical Formulations:
Ramosetron hydrochloride is available in various forms, including film-coated tablets and orally disintegrating tablets, approved for different indications. The film-coated tablets were approved in July 2008, while the orally disintegrating tablets were approved in August 2013.
Brand Name:
The brand name for Ramosetron hydrochloride is Nasea, which was launched in Japan for the treatment of chemotherapy-induced emesis. It was prepared through a four-step sequence involving the Vilsmeier-type coupling of 1-methylindole and 5-(1-pyrrolidoncarbonyl)-4,5,6,7-tetrahydro-Hl-benzimidazole hydrochloride.

Originator

Yamanouchi (Japan)

Biochem/physiol Actions

Ramosetron is a tetra hydrobenzimidazole derivative, containing an indole ring. It inhibits colon contraction mediated by serotonin, competitively. this pharmacologic property confers the drug an application in improving diarrhea-predominant inflammatory bowel syndrome. Ramosetron hydrochloride is used for PONV prophylaxis and treatment. However, ramosetron is currently only licenced for use in Japan and selected Southeast Asian countries.

InChI:InChI=1/C17H17N3O.ClH/c1-20-9-13(12-4-2-3-5-16(12)20)17(21)11-6-7-14-15(8-11)19-10-18-14;/h2-5,9-11H,6-8H2,1H3,(H,18,19);1H/t11-;/m1./s1

Synthetic route

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

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)

Conditions	Yield
With hydrogenchloride In ethanol; ethyl acetate at 70℃; for 1 - 12h; Product distribution / selectivity;	A n/a B n/a C n/a

Upstream product

• 132036-39-6 (R)-5-[(1-methyl-3-indolyl)carbonyl]-4,5,6,7-tetrahydro-1H-benzimidazole 
• 132036-88-5 ramosetron 

Related news

Mucoadhesive suppositories of Ramosetron hydrochloride (cas 132907-72-3) utilizing Carbopol®08/27/2019

Suppositories are the preferable dosage form for patients at home or experiencing nausea. Serotonin (5-HT3)-receptor antagonists are used to treat vomiting in intravenous or oral administration but not suppository form. Ramosetron hydrochloride (RAM) is a new 5-HT3 antagonist which effectively i...detailed

Relevant articles and documents

Novel 5-hydroxytryptamine (5-HT3) receptor antagonists. III. Pharmacological evaluations and molecular modeling studies of optically active 4,5,6,7-tetrahydro-1H-benzimidazole derivatives

The R- and S-enantiomers of the 4,5,6,7-tetrahydro-1H-benzimidazole derivatives 3-8 were prepared by optical resolution. Each R-isomer, except for 3, was almost two orders of magnitude more potent than its S-isomer as a 5-hydroxytryptamine (5-HT3/su

NOVEL PROCESS FOR PRODUCING RAMOSETRON OR ITS SALT

[PROBLEMS] To provide a novel process for producing ramosetron or its salt that is useful as a pharmaceutical, especially as a therapeutic and/or preventive agent for digestive symptoms caused by administration of an anti-malignant tumor agent, diarrheal-type irritable bowel syndrome, diarrheal symptoms of irritable bowel syndrome, etc. [MEANS FOR SOLVING PROBLEMS] Ramosetron or its salt can be produced by reacting any of compounds of the formula: (I) [wherein X is a halogen] or a salt thereof with 1-methyl-1H-indole in the presence of a Lewis acid selected from the group consisting of lower-alkylaluminum dihalides, di-lower-alkylaluminum halides, tri-lower-alkylaluminums and lower-alkylaluminum sesquihalides.