2-[(1H-1,3-benzodiazole-2-sulfonyl)methyl]-3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-1-ium-1-olate

• ChemBase ID: 172213
• Molecular Formular: C16H14F3N3O4S
• Molecular Mass: 401.3602696
• Monoisotopic Mass: 401.0657116
• SMILES: c1cccc2c1[nH]c(n2)S(=O)(=O)Cc1c(c(cc[n+]1[O-])OCC(F)(F)F)C
• Canonical SMILES: [O-][n+]1ccc(c(c1CS(=O)(=O)c1nc2c([nH]1)cccc2)C)OCC(F)(F)F
• InChI: InChI=1S/C16H14F3N3O4S/c1-10-13(22(23)7-6-14(10)26-9-16(17,18)19)8-27(24,25)15-20-11-4-2-3-5-12(11)21-15/h2-7H,8-9H2,1H3,(H,20,21)
• InChIKey: RQCPAMTYJRPELQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1H-1,3-benzodiazole-2-sulfonyl)methyl]-3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-1-ium-1-olate
• IUPAC Traditional name: 2-[(1H-1,3-benzodiazole-2-sulfonyl)methyl]-3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-1-ium-1-olate
• Synonyms: 2-[[[3-Methyl-1-oxido-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfonyl]-1H-benzimidazole; Lansoprazole Sulfone N-Oxide

Database IDs

• CAS Number: 953787-54-7
• PubChem SID: 164228123
• PubChem CID: 23656862

CALCULATED PROPERTIES

• Acid pKa: 6.3168907
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.8777368
• LogD (pH = 7.4): 1.2088696
• Log P: 1.93133
• Molar Refractivity: 90.8945 cm^3
• Polarizability: 35.316185 Å^3
• Polar Surface Area: 97.51 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; MethanolMethanol
• Apperance: Off-White SolidOff-White Solid
• Melting Point: 224-226°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - L175030

An impurity of Lansoprazole.

REFERENCES

• Barradell, L., et al.: Drugs, 44, 225 (1992)
• Aydogmus, Z., et al.: Acta Pharm. Sci., 48, 45 (1992)
• El-Sherif, Z., et al.: Chem. Pharm. Bull., 54, 814 (1992)