213476-12-1

Basic information

• Product Name: Lansoprazole N-Oxide
• Synonyms: Lansoprazole N-Oxide;2-[[[3-Methyl-1-oxido-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]Methyl]sulfinyl]-1H-benziMidazole;1H-BenziMidazole, 2-[[[3-Methyl-1-oxido-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]Methyl]sulfinyl]-;Lansoprazole IMpurity-N-Oxide (EP-IMpurity A);Lansoprazole EP IMpurity A;Lansoprazole impurity A;2-(((1H-benzo[d]imidazol-2-yl)sulfinyl)methyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine 1-oxide
• CAS NO: 213476-12-1
• Molecular Formula: C16H15F3N3O3S-
• Molecular Weight: 386.3688096
• Product Categories: Aromatics;Heterocycles;Impurities;Nitric Oxide Reagents;Sulfur & Selenium Compounds
• Mol File: 213476-12-1.mol

Chemical Properties

• Melting Point: 163-165°C (dec.)
• Boiling Point: 657.4±65.0 °C(Predicted)
• Appearance: /
• Density: 1.53±0.1 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: -20?C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.41±0.10(Predicted)
• CAS DataBase Reference: Lansoprazole N-Oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Lansoprazole N-Oxide(213476-12-1)
• EPA Substance Registry System: Lansoprazole N-Oxide(213476-12-1)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 213476-12-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Lansoprazole N-Oxide is used as an impurity in the bulk synthesis of Lansoprazole (L175000) for the development and manufacturing of pharmaceutical products. It is important to monitor and control the levels of this impurity to ensure the safety, efficacy, and quality of the final drug product.

Upstream product

• 163119-30-0 2-[[(3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzoimidazole 
• 163119-28-6 2-chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine-1-oxide 

Relevant articles and documents

Synthesis and characterization of metabolites and potential impurities of lansoprazole, an antiulcerative drug

Lansoprazole (Prevacid) is an antiulcerative drug used for the treatment of duodenal and gastric ulcers, reflux oesophagitis, and Zollinger-Ellison syndrome. During the bulk synthesis of lansoprazole, we have observed five impurities: lansoprazole N-oxide, lansoprazole sulfone N-oxide, lansoprazole sulfide, lansoprazole sulfone and N-aralkyl lansoprazole. The present work describes the synthesis and characterization of these impurities. Copyright Taylor & Francis Group, LLC.

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.