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

• ChemBase ID: 172215
• Molecular Formular: C16H14F3N3O3S
• Molecular Mass: 385.3608696
• Monoisotopic Mass: 385.07079698
• SMILES: c1cccc2c1[nH]c(n2)S(=O)Cc1c(c(cc[n+]1[O-])OCC(F)(F)F)C
• Canonical SMILES: O=S(c1nc2c([nH]1)cccc2)Cc1[n+]([O-])ccc(c1C)OCC(F)(F)F
• InChI: InChI=1S/C16H14F3N3O3S/c1-10-13(22(23)7-6-14(10)25-9-16(17,18)19)8-26(24)15-20-11-4-2-3-5-12(11)21-15/h2-7H,8-9H2,1H3,(H,20,21)
• InChIKey: OBGHBYDDJGHGNS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1H-1,3-benzodiazole-2-sulfinyl)methyl]-3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-1-ium-1-olate
• IUPAC Traditional name: 2-[(1H-1,3-benzodiazole-2-sulfinyl)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]sulfinyl]-1H-benzimidazole; Lansoprazole N-Oxide

Database IDs

• CAS Number: 213476-12-1
• PubChem SID: 164228125
• PubChem CID: 23656863

CALCULATED PROPERTIES

• Acid pKa: 9.346268
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.8243474
• LogD (pH = 7.4): 1.8201501
• Log P: 1.8244361
• Molar Refractivity: 91.8317 cm^3
• Polarizability: 34.68355 Å^3
• Polar Surface Area: 80.44 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 163-165°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L175035

An impurity of Lansoprazole (L175000) formed during the bulk synthesis of the drug.

REFERENCES

• Aydogmus, Z., et al.: Acta Pharm. Sci., 48, 45 (1990)
• Kubo, K., et al.: Chem. Pharm. Bull., 38, 2853 (1990)
• Barradell, L., et al.: Drugs, 44, 225 (1990)