2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole

• ChemBase ID: 172198
• Molecular Formular: C16H14F3N3O2S
• Molecular Mass: 369.3614696
• Monoisotopic Mass: 369.07588236
• SMILES: c1cccc2c1[nH]c(n2)[S@@](=O)Cc1c(c(ccn1)OCC(F)(F)F)C
• Canonical SMILES: O=[S@](c1nc2c([nH]1)cccc2)Cc1nccc(c1C)OCC(F)(F)F
• InChI: InChI=1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)/t25-/m0/s1
• InChIKey: MJIHNNLFOKEZEW-VWLOTQADSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
• IUPAC Traditional name: lansoprazol [inn-spanish]
• Synonyms: 2-[(S)-[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole; (S)-Lansoprazole; Levolansoprazole; (S)-Lansoprazole

Database IDs

• CAS Number: 138530-95-7
• PubChem SID: 164228108
• PubChem CID: 9578006

CALCULATED PROPERTIES

• Acid pKa: 9.34671
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.013967
• LogD (pH = 7.4): 3.0283315
• Log P: 3.0328553
• Molar Refractivity: 87.608 cm^3
• Polarizability: 34.145214 Å^3
• Polar Surface Area: 67.87 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Light Brown Solid
• Melting Point: 60-65°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L175015

The S-enantiomer of Lansoprazole; a gastric proton pump inhibitor. An antiulcerative.

REFERENCES

• Figgitt, D., et al.: Drugs, 60, 925 (2000)
• Katsuki, H., et al.: Eur. J. Clin. Pharmacol., 57, 709 (2000)
• Barradell, L.B., et al.: Drugs, 44, 225 (2000)
• Kim, K., et al.: Clin. Pharmacol. Ther., 72, 90 (2000)
• Niioka, T., et al.: Ther. Drug Monit., 28, 3