2-({[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}sulfanyl)-1H-1,3-benzodiazol-4-ol

• ChemBase ID: 170690
• Molecular Formular: C16H14F3N3O2S
• Molecular Mass: 369.3614696
• Monoisotopic Mass: 369.07588236
• SMILES: c1ccc(c2c1[nH]c(n2)SCc1c(c(ccn1)OCC(F)(F)F)C)O
• Canonical SMILES: Cc1c(nccc1OCC(F)(F)F)CSc1nc2c([nH]1)cccc2O
• InChI: InChI=1S/C16H14F3N3O2S/c1-9-11(20-6-5-13(9)24-8-16(17,18)19)7-25-15-21-10-3-2-4-12(23)14(10)22-15/h2-6,23H,7-8H2,1H3,(H,21,22)
• InChIKey: OQGIYDJVVFOGGO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}sulfanyl)-1H-1,3-benzodiazol-4-ol
• IUPAC Traditional name: 2-({[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}sulfanyl)-1H-1,3-benzodiazol-4-ol
• Synonyms: 2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]thio]-1H-benzimidazol-7-ol; 4-Hydroxy Lansoprazole Sulfide

Database IDs

• CAS Number: 131926-95-9
• PubChem SID: 164226600
• PubChem CID: 71749086

CALCULATED PROPERTIES

• Acid pKa: 8.211606
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.222846
• LogD (pH = 7.4): 3.7736232
• Log P: 3.856191
• Molar Refractivity: 88.2172 cm^3
• Polarizability: 34.205883 Å^3
• Polar Surface Area: 71.03 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H943700

A metabolite of Lansoprazole (L175000), as gastric pump inhibitor.

REFERENCES

• Uno, T., et al.: J. Clin. Pharmacol., 45, 690 (2005)
• Saito, M., et al.: Brit. J. Clin. Pharmacol., 59, 302 (2005)