132036-88-5

Basic information

• Product Name: RAMOSETRON
• Synonyms: (-)-(R)-1-Methylindol-3-yl 4,5,6,7-tetrahydro-5-benzimidazolylketone;Methanone, (1-methyl-1H-indol-3-yl)(4,5,6,7-tetrahydro-1H-benzimidazol-5-yl)-, (R)-;Methanone, (1-methyl-1H-indol-3-yl)[(5R)-4,5,6,7-tetrahydro-1H-benzimidazol-5-yl]- (9CI);Nasea;Nor-YM 060;(R)-5-[(1-METHYLINDOLE-3-YL)CARBONYL]-4,5,6,7-TETRAHYDRO-1H-BEZIMIDAZOLE, 98+%;(1-Methyl-1H-indol-3-yl)[[(5R)-4,5,6,7-tetrahydro-1H-benzimidazol]-5α-yl] ketone;(5R)-5α-[(1-Methyl-1H-indole-3-yl)carbonyl]-4,5,6,7-tetrahydro-1H-benzimidazole
• CAS NO: 132036-88-5
• Molecular Formula: C₁₇H₁₇N₃O
• Molecular Weight: 279.34
• Mol File: 132036-88-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 579.693 °C at 760 mmHg
• Flash Point: 304.388 °C
• Appearance: /
• Density: 1.338 g/cm³
• Vapor Pressure: 1.96E-13mmHg at 25°C
• Refractive Index: 1.707
• PKA: 14.53±0.40(Predicted)
• CAS DataBase Reference: RAMOSETRON(CAS DataBase Reference)
• NIST Chemistry Reference: RAMOSETRON(132036-88-5)
• EPA Substance Registry System: RAMOSETRON(132036-88-5)

Safety Data

• Hazardous Substances Data: 132036-88-5(Hazardous Substances Data)

Usage

Uses

Ramosetron is a serotonin 5HT3 receptor antagonist.

InChI:InChI=1/C17H17N3O/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)/t11-/m0/s1

Synthetic route

1-methylindole (603-76-9) + (R)-4,5,6,7-tetrahydro-1H-benzimidazole-5-carboxylic acid (912920-60-6) → ramosetron (132036-88-5)

Conditions	Yield
In tetrahydrofuran at 50℃; for 2h; Temperature; Microwave irradiation;	95.2%

1-methylindole (603-76-9) + (R)-4,5,6,7-tetrahydro-1H-benzoimidazole-5-carbonyl chloride → ramosetron (132036-88-5)

Conditions	Yield
Stage #1: 1-methylindole; (R)-4,5,6,7-tetrahydro-1H-benzoimidazole-5-carbonyl chloride; triethyl aluminum sesquichloride In toluene at -40℃; for 3h; Friedel Crafts Acylation; Stage #2: With water In tetrahydrofuran; toluene Stage #3: With sodium hydroxide In water; butanone Product distribution / selectivity;
Stage #1: 1-methylindole; (R)-4,5,6,7-tetrahydro-1H-benzoimidazole-5-carbonyl chloride; diethylaluminium chloride In toluene at -25℃; for 2h; Friedel Crafts Acylation; Stage #2: With water In tetrahydrofuran; toluene at 0 - 45℃; Stage #3: With sodium hydroxide In water; butanone Product distribution / selectivity;

ramosetron (132036-88-5) → 5-(1-Methyl-1H-indole-3-carbonyl)-1,3-dihydro-benzoimidazol-2-one + (S)-6-(1-Methyl-1H-indole-3-carbonyl)-1,5,6,7-tetrahydro-benzoimidazol-4-one + 5-(1-Methyl-1H-indole-3-carbonyl)-1,5,6,7-tetrahydro-benzoimidazol-4-one + (1H-Benzoimidazol-5-yl)-(1-methyl-1H-indol-3-yl)-methanone

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile for 22h; Heating; Yield given. Yields of byproduct given;
With 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile for 22h; Heating; Yields of byproduct given;

ramosetron (132036-88-5) → 5-(1-Methyl-1H-indole-3-carbonyl)-1,3-dihydro-benzoimidazol-2-one + 5-(1-Methyl-1H-indole-3-carbonyl)-1,5,6,7-tetrahydro-benzoimidazol-4-one + ((5S,7S)-7-Hydroxy-4,5,6,7-tetrahydro-3H-benzoimidazol-5-yl)-(1-methyl-1H-indol-3-yl)-methanone

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile for 22h; Heating; Yields of byproduct given;	A 70 mg B n/a C n/a
With 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile for 22h; Heating; Yields of byproduct given;	A n/a B 155 mg C n/a
With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); oxygen 1.) MeCN, reflux, 22 h, 2.) EtOH, 30 min; Yield given. Multistep reaction;	A 70 mg B 155 mg C n/a

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

• 603-76-9 1-methylindole 
• 912920-60-6 (R)-4,5,6,7-tetrahydro-1H-benzimidazole-5-carboxylic acid 

Downstream Products

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

Related news

Inhibitory effect of the selective serotonin 5-HT3 receptor antagonist RAMOSETRON (cas 132036-88-5) on duodenal acidification-induced gastric hypersensitivity in rats08/05/2019

Irritable bowel syndrome (IBS) and functional dyspepsia (FD) are both functional gastrointestinal disorders and frequently co-occur in patients. While one cause of FD appears to be gastric hypersensitivity, whether the hypersensitivity is affected by IBS treatments remains unclear, given the lac...detailed

Effect of RAMOSETRON (cas 132036-88-5) on conditioned emotional stress-induced colonic dysfunction as a model of irritable bowel syndrome in rats08/04/2019

The aim of this study was to establish a pathophysiologic model of irritable bowel syndrome, and then to evaluate the pharmaceutical efficacy of ramosetron, a potent serotonin 3 (5-HT3) receptor antagonist, and other anti-irritable bowel syndrome agents in this model. Rats stressed by a conditio...detailed

Comparison of RAMOSETRON (cas 132036-88-5) with ondansetron for prevention of postoperative nausea and vomiting in patients undergoing gynaecological surgery08/03/2019

BackgroundRamosetron is a new selective 5-hydroxytryptamine type 3 (5-HT3) receptor antagonist that reportedly has more potent antiemetic effects compared with other 5-HT3 receptor antagonists. The purpose of this study was to evaluate the efficacy of ramosetron for the prevention of postoperati...detailed

Comparison of RAMOSETRON (cas 132036-88-5), dexamethasone, and a combination of RAMOSETRON (cas 132036-88-5) and dexamethasone for the prevention of postoperative nausea and vomiting in Korean women undergoing thyroidectomy: A double-blind, randomized, controlled study08/02/2019

Background: Thyroidectomy is associated with a relatively high incidence of postoperative nausea and vomiting (PONV), ranging from 51% to 76%. Because these symptoms are distressing for patients, prophylactic medication to avoid or reduce PONV is recommended.Objective: The aim of the present stu...detailed

Intravenous, Oral, and the Combination of Intravenous and Oral RAMOSETRON (cas 132036-88-5) for the Prevention of Nausea and Vomiting After Laparoscopic Cholecystectomy: A Randomized, Double-Blind, Controlled Trial08/01/2019

BackgroundPatients undergoing general anesthesia for laparoscopic cholecystectomy have a high risk of postoperative nausea and vomiting (PONV) with incidences up to 75%. Ramosetron, a serotonin subtype 3 (5-HT3) antagonist, has been shown to be effective as an antiemetic after chemotherapy and s...detailed

RAMOSETRON (cas 132036-88-5) Reduces Symptoms of Irritable Bowel Syndrome With Diarrhea and Improves Quality of Life in Women07/31/2019

Background & AimsPrevious studies have indicated that serotonin-3–receptor antagonists might have a sex-specific effect in patients with irritable bowel syndrome with diarrhea (IBS-D). Alosetron has been approved for the treatment of only women, and ramosetron has been approved for the treatmen...detailed

RAMOSETRON (cas 132036-88-5) vs. RAMOSETRON (cas 132036-88-5) plus dexamethasone for the prevention of postoperative nausea and vomiting (PONV) after laparoscopic cholecystectomy: Prospective, randomized, and double-blind study07/30/2019

IntroductionUp to 75% of the patients undergoing laparoscopic cholecystectomy develop postoperative nausea and vomiting (PONV). Both ramosetron, a serotonin subtype 3 (5-HT3) antagonist, and dexamethasone are effective for PONV prophylaxis following laparoscopic cholecystectomy but their combine...detailed

Effect of RAMOSETRON (cas 132036-88-5) on Stool Consistency in Male Patients With Irritable Bowel Syndrome With Diarrhea07/29/2019

Background & AimsRamosetron, a serotonin (5-hydroxytryptamine)-3 receptor antagonist with high selectivity, reduced stress-induced diarrhea and defecation caused by corticotropin-releasing hormone in rats. However, there have been no clinical trials of its effect in patients with diarrhea and ir...detailed

Effects of prophylactic RAMOSETRON (cas 132036-88-5) and ondansetron on corrected QT interval during general anesthesia07/28/2019

Study ObjectiveTo evaluate whether ramosetron increases the corrected QT (QTc) interval.detailed

Comparison of RAMOSETRON (cas 132036-88-5) With Ondansetron for Prevention of Intrathecal Morphine-Induced Nausea and Vomiting After Primary Total Knee Arthroplasty: A Randomized Control Trial07/27/2019

BackgroundSpinal anesthesia with intrathecal morphine is a reliable, easy to apply, and cost effective method for controlling pain after total knee arthroplasty (TKA). However, postoperative nausea and vomiting (PONV) is a major concern. 5-Hydroxytryptamine receptor 3 (5-HT3) antagonists like on...detailed

Relevant articles and documents

Preparation method of ramosetron

The invention discloses a preparation method of ramosetron, which includes the following steps: (1) dissolving TiCl4 in a hexane solution and adding carrier particles to the solution, performing ultrasonic dispersion for 3-5 h and allowing the mixture to stand for 8-10 h, evaporating the mixture to remove hexane, and drying the mixture to obtain a carrier supporting the TiCl4; (2) dispersing the carrier supporting the TiCl4 in tetrahydrofuran, adding 4,5,6,7-tetrahydro-1H-benzimidazole-5-formic acid, heating the mixture to 40-50 DEG C, performing microwave irradiation and dropwise adding N-methylindole under stirring, and then performing a reaction continuously for 2-4 h, after the reaction is finished, stopping the microwave irradiation, cooling the mixture to room temperature, filteringthe mixture and adding water to the mixture, performing vibrating mixing uniformly, centrifugally layering the mixture, collecting an organic layer, regulating pH value, evaporating the mixture to remove the solvent and drying the mixture to prepare the ramosetron. The method is low in requirement on operation conditions, is low in generation of byproducts, is high in product purity and is high inyield.

TETRAHYDROBENZIMIDAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME

A tetrahydrobenzimidazole derivative represented by formula (I) : STR1 wherein Het represents a heterocyclic group which may be substituted with 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a cycloalkyl-lower alkyl group, an aralkyl group, a lower alkoxy group, a nitro group, a hydroxyl group, a lower alkoxycarbonyl group, and a halogen atom; and X represents a single bond or--NH--which is bonded to the carbon atom or nitrogen atom of the heterocyclic ring, or a pharmaceutically acceptable salt thereof.The compound of formula (I) and a salt thereof exhibits antagonism against 5-HT 3 receptor.