953787-54-7

Basic information

• Product Name: Lansoprazole Sulfone N-Oxide
• Synonyms: Lansoprazole Sulfone N-Oxide;2-[[[3-Methyl-1-oxido-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl]sulfonyl]-1H-benzimidazole;Lansoprazole related substance A;2-[[[3-Methyl-1-oxido-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]Methyl]sulfonyl]-;Lansoprazole IMpurity-Sulfone N-Oxide;2-(((1H-benzo[d]imidazol-2-yl)sulfonyl)methyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine 1-oxide;Lansoprazole impurity L;2-[[[3-Methyl-1-oxido-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfonyl]-1H-benzimidazole
• CAS NO: 953787-54-7
• Molecular Formula: C16H14F3N3O4S
• Molecular Weight: 401.3602696
• Product Categories: Aromatics;Heterocycles;Impurities;Nitric Oxide Reagents;Sulfur & Selenium Compounds
• Mol File: 953787-54-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 224-226°C
• Boiling Point: 654.605 °C at 760 mmHg
• Flash Point: 349.693 °C
• Appearance: /
• Density: 1.532 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Lansoprazole Sulfone N-Oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Lansoprazole Sulfone N-Oxide(953787-54-7)
• EPA Substance Registry System: Lansoprazole Sulfone N-Oxide(953787-54-7)

Safety Data

• Hazardous Substances Data: 953787-54-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-White SolidOff-White Solid

Uses

An impurity of Lansoprazole.

InChI:InChI=1/C16H14F3N3O4S/c1-10-13(22(23)7-6-14(10)26-9-16(17,18)19)8-27(24,25)15-20-11-4-2-3-5-12(11)21-15/h2-7H,8-9H2,1H3,(H,20,21)

Upstream product

• 163119-30-0 2-[[(3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzoimidazole 
• 103577-45-3 lansoprasole 
• 103577-40-8 lansoprazole sulfide 
• 163119-28-6 2-chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine-1-oxide 

Relevant articles and documents

Forced degradation studies of lansoprazole using LC-ESI HRMS and 1H-NMR experiments: in vitro toxicity evaluation of major degradation products

Regulatory agencies from all over the world have set up stringent guidelines with regard to drug degradation products due to their toxic effects or carcinogenicity. Lansoprazole, a proton-pump inhibitor, was subjected to forced degradation studies as per ICH guidelines Q1A (R2). The drug was found to degrade under acidic, basic, neutral hydrolysis and oxidative stress conditions, whereas it was found to be stable under thermal and photolytic conditions. The chromatographic separation of the drug and its degradation products were achieved on a Hiber Purospher, C18 (250?×?4.6?mm, 5?μ) column using 10?mM ammonium acetate and acetonitrile as a mobile phase in a gradient elution mode at a flow rate of 1.0?ml/min. The eight degradation products (DP1–8) were identified and characterized by UPLC/ESI/HRMS with in-source CID experiments combined with accurate mass measurements. DP-1, DP-2 and DP-3 were formed in acidic, DP-4 in basic, DP-5 in neutral and DP-1, DP-6, DP-7 and DP-8 were in oxidation stress condition Among eight degradation products, five were hitherto unknown degradation products. In addition, one of the major degradation products, DP-2, was isolated by using semi preparative HPLC and other two, DP-6 and DP-7 were synthesized. The cytotoxic effect of these degradation products (DP-2, DP-6 and DP-7) were tested on normal human cells such as HEK 293 (embryonic kidney cells) and RWPE-1(normal prostate epithelial cells) by MTT assay. From the results of cytotoxicity, it was found that lansoprazole as well as its degradation products (DP-2, DP-6 and DP-7) were nontoxic up to 50-μM concentrations, and the latter showed slightly higher cytotoxicity when compared with that of lansoprazole. DNA binding studies using spectroscopic techniques indicate that DP-2, DP-6 and DP-7 molecules interact with ctDNA and may bind to its surface. Copyright

Efficient synthesis of N-Oxide derivatives: Substituted 2-(2-(pyridyl-N-oxide)methylsulphinyl)benzimidazoles

Different substituted 2-chloromethylpyridyl derivatives (6a-d) were oxidized with mCPBA to give the respective 2-chloromethylpyridine-N-oxide derivatives (7a-d) at low temperature, which on condensation with 2-mercapto-1H-benzimidazole (8a-c) in the presence of aprotic solvents give the 2-[[(pyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzimidazole (9a-d) in good yield. Finally, 9a-d oxidized with mCPBA in chlorinated solvent gives a mixture of 2-[[(pyridin-2-yl-1-oxide)methyl]sulfonyl]-1H-benzimidazole (3a-d, 10%) and 2-[[(pyridin-2-yl-1-oxide) methyl]sulfinyl]-1H-benzimidazole (4a-d, 90%) derivatives. Copyright Taylor & Francis Group, LLC.