5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1-sodio-1H-1,3-benzodiazole

• ChemBase ID: 73085
• Molecular Formular: C17H18N3NaO3S
• Molecular Mass: 367.39789
• Monoisotopic Mass: 367.09665673
• SMILES: c1(ccc2c(c1)nc(n2[Na])S(=O)Cc1ncc(c(c1C)OC)C)OC
• Canonical SMILES: COc1ccc2c(c1)nc(n2[Na])S(=O)Cc1ncc(c(c1C)OC)C
• InChI: InChI=1S/C17H18N3O3S.Na/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17;/h5-8H,9H2,1-4H3;/q-1;+1
• InChIKey: RYXPMWYHEBGTRV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1-sodio-1H-1,3-benzodiazole
• IUPAC Traditional name: 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1-sodio-1,3-benzodiazole
• Synonyms: Sompraz; Zoleri; Lucen; Esopral; Axagon; Nexiam; Esomeprazole sodium

Database IDs

• CAS Number: 161796-78-7
• PubChem SID: 162038005
• PubChem CID: 10959536

CALCULATED PROPERTIES

• Acid pKa: 17.020626
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.37600845
• LogD (pH = 7.4): 0.44819438
• Log P: 0.4492
• Molar Refractivity: 94.273 cm^3
• Polarizability: 39.000565 Å^3
• Polar Surface Area: 66.24 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: ATPase

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2233

Research Area: Cancer
Biological Activity:
Esomeprazole sodium (Nexium) is a sodium salt of esomeprazole that is a potent proton pump inhibitor with an IC50 of 0.076 mg/kg. Esomeprazole sodium (Nexium) suppresses gastric acid secretion by specific inhibition of the H+/K+-ATPase in the gastric parietal cell. Esomeprazole sodium (Nexium) is used in the treatment of dyspepsia, peptic ulcer disease, gastroesophageal reflux disease and Zollinger-Ellison syndrome. Esomeprazole is the S-enantiomer of omeprazole. The S- and R-isomers of omeprazole are protonated and converted in the acidic compartment of the parietal cell forming the active inhibitor, the achiral sulphenamide. By acting specifically on the proton pump, esomeprazole blocks the final step in acid production, thus reducing gastric acidity. This effect is dose-related up to a daily dose of 20 to 40 mg and leads to inhibition of gastric acid secretion. [1][2]

REFERENCES

• Bastaki SM et al. Mol Cell Biochem. 2008 Feb;309(1-2):167-75.