4-methoxy-2-[({5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl}sulfinyl)methyl]-3,5-dimethylpyridine

• ChemBase ID: 178142
• Molecular Formular: C16H18N4O3S
• Molecular Mass: 346.40412
• Monoisotopic Mass: 346.10996146
• SMILES: c1c(nc2c(c1)[nH]c(n2)S(=O)Cc1c(c(c(cn1)C)OC)C)OC
• Canonical SMILES: COc1ccc2c(n1)nc([nH]2)S(=O)Cc1ncc(c(c1C)OC)C
• InChI: InChI=1S/C16H18N4O3S/c1-9-7-17-12(10(2)14(9)23-4)8-24(21)16-18-11-5-6-13(22-3)19-15(11)20-16/h5-7H,8H2,1-4H3,(H,18,19,20)
• InChIKey: ZBFDAUIVDSSISP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methoxy-2-[({5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl}sulfinyl)methyl]-3,5-dimethylpyridine; 4-methoxy-2-[({5-methoxy-1H-imidazo[4,5-b]pyridin-2-yl}sulfinyl)methyl]-3,5-dimethylpyridine
• IUPAC Traditional name: 4-methoxy-2-[({5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl}sulfinyl)methyl]-3,5-dimethylpyridine; tenatoprazole
• Synonyms: Protop; TU-199; Ulsacare; Tenatoprazole; 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-imidazo[4,5-b]pyridine; 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-imidazo[4,5-b]pyridine; TU 199; Tenatoprazole

Database IDs

• CAS Number: 113712-98-4; 113712-98-4
• PubChem SID: 164234052
• PubChem CID: 636411

CALCULATED PROPERTIES

• Acid pKa: 8.820832
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.1058762
• LogD (pH = 7.4): 2.162608
• Log P: 2.1777563
• Molar Refractivity: 91.7715 cm^3
• Polarizability: 35.823494 Å^3
• Polar Surface Area: 89.99 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Off-White to Light Pink Solid
• Melting Point: >155°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

Pharmacology Properties

• Mechanism of Action: H-K ATPase inhibitor

Product Information

• Application(s): Antiulcer; Gastric secretion inhibitor

DETAILS

Toronto Research Chemicals - T018250

A proton pump inhibitor for reduction and/or prevention of gastrointestinal disorders.

REFERENCES

• Richardson, P., et al.: Drugs, 56, 307 (1998)
• Uchiyama, K., et al.: J. Pharm. Pharmacol., 51, 457 (1998)
• Rohss, K., et al.: Dig. Dis. Sci., 47, 954 (1998)
• Galmiche, J., et al.: Aliment. Pharmacol. Ther., 19, 655 (1998)
• Jpn.J.Pharmacol. (64, Suppl. 1, 280P, 1994) Effects of TU-199, a novel H+,K+-ATPase inhibitor, on stimulated gastric acid secretions in rats and dogs.