117976-47-3

Basic information

• Product Name: Rabeprazole Sulfone
• Synonyms: 2-[[[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfonyl]-1H-benzimidazol;2-[[[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfonyl]-1H-benzimidazole;Rabeprazole IMpurity-sulphone;Rabeprazole IMpurity E;Rabeprazole Related CoMpound D;Rabeprazole Related Compound D (25 mg) (2-[[[4-(3-Methoxypropoxy)-3-methyl-2-pyridyl]methyl]sulfonyl]benzimidazole);Rabeprazole USP RC D;Rabeprazole EP Impurity A
• CAS NO: 117976-47-3
• Molecular Formula: C₁₈H₂₁N₃O₄S
• Molecular Weight: 375.447
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Rabeprazole Sodium;Sulfur & Selenium Compounds
• Mol File: 117976-47-3.mol

Chemical Properties

• Melting Point: 64-66°C
• Boiling Point: 603.718°C at 760 mmHg
• Flash Point: 318.917°C
• Appearance: /
• Density: 1.308g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• PKA: 9.04±0.10(Predicted)
• CAS DataBase Reference: Rabeprazole Sulfone(CAS DataBase Reference)
• NIST Chemistry Reference: Rabeprazole Sulfone(117976-47-3)
• EPA Substance Registry System: Rabeprazole Sulfone(117976-47-3)

Safety Data

• Hazardous Substances Data: 117976-47-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Rabeprazole Sulfone is used as a pharmaceutical impurity for Rabeprazole (R070500). It is an essential component in the development and manufacturing of Rabeprazole-based medications, ensuring the quality and safety of the final product.
Used in Research and Development:
Rabeprazole Sulfone is used as a research compound for studying the metabolism and pharmacokinetics of Rabeprazole. It helps researchers understand the drug's behavior in the body and its potential side effects, leading to the development of safer and more effective medications.
Used in Quality Control:
Rabeprazole Sulfone is used as a reference standard in the quality control and analysis of Rabeprazole-based pharmaceutical products. It helps ensure that the active pharmaceutical ingredient (API) meets the required specifications and is free from impurities.
Used in Metabolism Studies:
Rabeprazole Sulfone is used as a metabolite in the study of Rabeprazole's metabolic pathways. Understanding the metabolic fate of Rabeprazole can provide valuable insights into drug interactions, drug resistance, and the development of personalized medicine strategies.

InChI:InChI=1/C18H21N3O4S/c1-13-16(19-9-8-17(13)25-11-5-10-24-2)12-26(22,23)18-20-14-6-3-4-7-15(14)21-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,20,21)

Upstream product

• 117977-21-6 rabeprazole sulfide 
• 103312-62-5 2-[(4-chloro-3-methylpyridin-2-yl)methylsulfanyl]-1H-benzoimidazole 
• 152402-97-6 2-chloromethyl-4-chloro-3-methylpyridine hydrochloride 
• 924663-37-6 2-[(4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl-1-oxide)methylsulfonyl]-1H-benzoimidazole 
• 134469-07-1 Benzimidazol-2-thiol 
• 59886-90-7 4-chloro-2,3-dimethylpyridine-N-oxide 
• 37699-43-7 2,3-dimethyl-4-nitropyridine N-oxide 

Downstream Products

• 117976-90-6 Rabeprazole sodium 

Relevant articles and documents

Synthesis of metabolites and related substances of rabeprazole, an anti-ulcerative drug

Rabeprazole sodium (Aciphex) is a gastric proton pump inhibitor used for the prevention and treatment of gastric acid-related diseases. During the synthesis of bulk drug of rabeprazole sodium, we have observed metabolites rabeprazole sulfide and rabeprazole sulfone and related substances rabeprazole-N-oxide, rabeprazole sulfone-N-oxide, N-aralkyl rabeprazole, chloro rabeprazole, and methoxy rabeprazole as impurities in the drug substance. The present work describes the synthesis and characterization of these compounds. Copyright Taylor & Francis Group, LLC.

Method for producing proton pump inhibitor compound having optical activity

A highly pure optically active proton pump inhibitor compound can be produced safely and inexpensively in a high yield and enantioselectivity by a method of producing an optically active sulfoxide of Formula 2 or a salt thereof, comprising oxidizing a sulfide of Formula 1 or a salt thereof with hydrogen peroxide using an iron salt in the presence of a chiral ligand of Formula 3; wherein A is CH or N; R1 is hydrogen atom, an alkyl optionally substituted by halogen(s), or an alkoxy optionally substituted by halogen(s); one to three R2 may exist, and each of R2 is independently an alkyl, a dialkylamino, or an alkoxy optionally substituted by halogen(s) or alkoxy(s); each of R3 is independently hydrogen atom, a halogen, cyano or the like; R4 is a tertiary alkyl; and * and ** represent respectively R configuration or S configuration.

Rabeprazole correlate D synthetic method

The present invention relates to a rabeprazole correlate D synthesis method, which comprises that: (1) in the presence of an excess oxidizing agent, a thioether compound 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl]thio]benzimidazole is oxidized to produce an oxide C; and (2) in the presence of an acid and a reducing agent, the oxide C formed in the step (1) is reduced so as to form the rabeprazole correlate D.

Synthetic studies connected with the preparation of H+/K +-ATPase inhibitors rabeprazole and lansoprazole

Synthesis of lansoprazole and rabeprazole using common intermediates is devised. The common intermediates, 2-[(4-nitro-3-methylpyridin-2-yl) methanesulfanyl]-1H-benzoimidazole and 2-[(4-chloro-3-methyl-pyridin-2-yl) methanesulfanyl]-1H-benzoimidazole, were prepared in several ways.

MORPHINE SULPHATE FORMULATIONS

Described is a pellet composition comprising a core element comprising morphine sulfate, a filler and a binder, wherein the morphine sulfate, calculated as the anhydrous form, comprises about 50 wt% to about 85 wt% of the total weight of the core element; and a coating disposed on at least a portion of the core element, the coating comprising an insoluble matrix polymer which is insoluble at pH 1 to 7.5; an enteric polymer which is insoluble at pH 1 to 4 and soluble at pH 6 to 7.5; and an acid soluble polymer which is soluble at a pH of 1 to 4, wherein the ratio of the acid soluble polymer to the enteric polymer is 1.45:1 to 2.5:1 on a weight basis. Also described are dosage forms comprising the disclosed pellets.