138530-95-7

Basic information

• Product Name: (S)-Lansoprazole
• Synonyms: (S)-Lansoprazole;1H-Benzimidazole, 2-[(S)-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]- (9CI);1H-Benzimidazole, 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-, (S)-;Levolansoprazole;2-[(S)-[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole;2-[(S)-[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]Methyl]sulfinyl]-;Lansoprazole S-IsoMer;(S)-2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole
• CAS NO: 138530-95-7
• Molecular Formula: C₁₆H₁₄F₃N₃O₂S
• Molecular Weight: 369.3614696
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 138530-95-7.mol

Chemical Properties

• Melting Point: 60-65°C
• Boiling Point: 555.8°Cat760mmHg
• Flash Point: 289.9°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 9.56±0.10(Predicted)
• CAS DataBase Reference: (S)-Lansoprazole(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Lansoprazole(138530-95-7)
• EPA Substance Registry System: (S)-Lansoprazole(138530-95-7)

Safety Data

• Hazardous Substances Data: 138530-95-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-Lansoprazole is used as a gastric proton pump inhibitor for treating conditions associated with excessive gastric acid production, such as gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome. It helps in reducing the symptoms and promoting healing of the affected areas by lowering the acidity in the stomach.
Used in Gastroenterology:
(S)-Lansoprazole is used as an antiulcerative agent for the management of ulcers in the stomach and duodenum. By inhibiting gastric acid secretion, it aids in the healing process and reduces the risk of complications such as bleeding or perforation.
Used in Combination Therapy:
(S)-Lansoprazole is also used in combination with antibiotics for the eradication of Helicobacter pylori, a bacterium that can cause peptic ulcers and increase the risk of gastric cancer. This combination therapy helps in effectively treating the infection and reducing the likelihood of ulcer recurrence.

InChI:InChI=1/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)/t25-/m0/s1

Upstream product

• 103577-40-8 lansoprazole sulfide 
• 103577-45-3 lansoprasole 
• 1240684-31-4 C₂₆H₂₈F₃N₃O₅S₂ 
• 134469-07-1 Benzimidazol-2-thiol 
• 142384-07-4 (S)-(-)-2-(3-methyl-4-nitropyridin-2-ylmethansulfinyl)-1H-benzimidazole 
• 75-89-8 2,2,2-trifluoroethanol 

Downstream Products

• 503833-45-2 isopropyl 1-[(S)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazol-l-yl] ethyl carbonate 

Relevant articles and documents

Method for preparing dexlansoprazole through catalysis of hexadentate ligand

The invention belongs to the technical field of chemical engineering, and particularly provides a method for preparing dexlansoprazole through catalysis of a hexadentate ligand. Under the catalysis ofa complex formed by a Ti(O-iPr)4 catalyst and a self-made hexadentate ligand, lansoprazole thioether is subjected to asymmetric oxidation, and dextral lansoprazole is obtained. The hexadentate ligandused in the method is simple to prepare and high in yield, and the complex formed by the hexadentate ligand and the Ti(O-iPr)4 catalyst is high in catalytic efficiency and high in enantiomeric excessvalue.

Method for preparing chiral sulfoxide drugs in water phase

The invention relates to the field of chiral drug preparation, in particular to a method for preparing chiral sulfoxide drugs in a water phase. The method for preparing the chiral sulfoxide drugs in the water phase comprises the following steps: using a hydrogen peroxide solution as oxidant, using a temperature-sensitive ferrocene chiral amino acid titanium complex as a catalyst and using prochiral thioether as a substrate in the pure water phase to perform an asymmetric oxidation reaction to synthesize the chiral sulfoxide drugs. The temperature-sensitive ferrocene chiral amino acid titaniumcomplex catalyst can be utilized to catalyze the asymmetric oxidation reaction of thioether in the pure water phase and has the characteristics of high catalytic efficiency and easy recovery of the catalyst.

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.

A catalytic asymmetric oxidizing thioether preparation of chiral pharmaceutical method

The invention provides a preparation method of a chiral sulfoxide medicament though catalysis of asymmetric oxidation of sulfides compounds. A chiral complex formed by quadridentate nitrogen organic ligand and metal manganese compound as a catalyst and hydrogen peroxide as an oxidant are used for asymmetric catalytic oxidation of prochiral thioether compound, so as to obtain the corresponding chiral sulfoxide medicament compounds including S-omeprazole, S-lansoprazole, S-pantoprazole, S-rabeprazole, R-Modafinil and R-sulindac. The reaction has the advantages of cleaness, mild reaction conditions, high conversion rate and antipodal selectivity, and shows industrial prospects.

Enantioselective Separation over a Chiral Biphenol-Based Metal-Organic Framework

A chiral porous 3D metal-organic framework (MOF) is constructed from an enantiopure carboxylate ligand of 1,1′-biphenol, which can be utilized as adsorbent for the separation of aromatic alcohols and sulfoxides with enantioselectivity of up to 99.4%. Single-crystal X-ray diffraction analysis reveals the binding sites and host-guest interactions clearly, providing microscopic insight into the origin of the enantiosorption in the framework.

Synthesis of Esomeprazole and Related Proton Pump Inhibitors through Iron-Catalyzed Enantioselective Sulfoxidation

We report here an application of iron catalysis for the kilogram scale asymmetric synthesis of a proton pump inhibitor, esomeprazole, in 87% yield and 99.4% ee by catalytic sulfoxidation with hydrogen peroxide using an iron salt/chiral Schiff base in combination with a carboxylate salt. Under similar reaction conditions, other proton pump inhibitors such as (S)-lansoprazole, (S)-rabeprazole, and (S)-pantoprazole, were also synthesized in high yield and ee. A carboxylate additive was crucial for the success of this reaction, and we consider that it coordinates to the active iron species, and it also acts as a hydrogen-bond acceptor to coordinate to the substrate through the imidazole NH.

Ultrafast chiral separations for high throughput enantiopurity analysis

Recent developments in fast chromatographic enantioseparations now make high throughput analysis of enantiopurity on the order of a few seconds achievable. Nevertheless, routine chromatographic determinations of enantiopurity to support stereochemical investigations in pharmaceutical research and development, synthetic chemistry and bioanalysis are still typically performed on the 5-20 min timescale, with many practitioners believing that sub-minute enantioseparations are not representative of the molecules encountered in day to day research. In this study we develop ultrafast chromatographic enantioseparations for a variety of pharmaceutically-related drugs and intermediates, showing that sub-minute resolutions are now possible in the vast majority of cases by both supercritical fluid chromatography (SFC) and reversed phase liquid chromatography (RP-LC). Examples are provided illustrating how such methods can be routinely developed and used for ultrafast high throughput analysis to support enantioselective synthesis investigations.

Ti-Salan catalyzed asymmetric sulfoxidation of pyridylmethylthiobenzimidazoles to optically pure proton pump inhibitors

The asymmetric sulfoxidation of two pyridylmethylthiobenzimidazoles to anti-ulcer drugs of the PPI family (S)-omeprazole and (R)-lansoprazole with hydrogen peroxide, mediated by a series of chiral titanium(IV) salan complexes is reported. High sulfoxide yields (up to?>95%) and enantioselectivities (up to 94% ee) have been achieved. The introduction of electron-withdrawing substituents leads to less active and less enantioselective catalysts. Like for the previously reported Ti-salalen catalyzed sulfoxidations, the temperature dependence of the sulfoxidation enantioselectivity in the presence of Ti-salan complexes is nonmonotonic, demonstrating isoinversion behavior with decreasing temperature. The oxidation is likely rate-limited by the formation of the active (presumably peroxotitanium(IV)) species, followed by a faster oxygen transfer to the substrate.

ION PAIR CATALYSIS OF TUNGSTATE AND MOLYBDATE

D The present invention relates to ion pair catalysts (I) comprising the cationic bisguanidinium ligand (A) and diperoxomolybdate anion (B). The present invention also relates to ion pair catalysts (III) comprising the cationic bisguanidinium ligand (C) and peroxotungstate anion (D). It further relates to the use of the said catalysts in the manufacture of enantiomerically enriched sulfoxides.