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
• Article Data: 5

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

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 117976-47-3 differently. You can refer to the following data:
1. A metabolite of Rabeprazole (R070500).
2. Rabeprazole Sulfone (Rabeprazole EP Impurity A) is a metabolite of Rabeprazole (R070500).

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 
• 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 
• 152402-97-6 2-chloromethyl-4-chloro-3-methylpyridine hydrochloride 
• 103312-62-5 2-[(4-chloro-3-methylpyridin-2-yl)methylsulfanyl]-1H-benzoimidazole 
• 924663-37-6 2-[(4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl-1-oxide)methylsulfonyl]-1H-benzoimidazole 

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.

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.