5-[(4-{2-[5-(2-hydroxyethyl)pyridin-2-yl]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione

• ChemBase ID: 171129
• Molecular Formular: C19H20N2O4S
• Molecular Mass: 372.4381
• Monoisotopic Mass: 372.11437813
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)CCO
• Canonical SMILES: OCCc1ccc(nc1)CCOc1ccc(cc1)CC1SC(=O)NC1=O
• InChI: InChI=1S/C19H20N2O4S/c22-9-7-14-1-4-15(20-12-14)8-10-25-16-5-2-13(3-6-16)11-17-18(23)21-19(24)26-17/h1-6,12,17,22H,7-11H2,(H,21,23,24)
• InChIKey: TUXGNBJVZUQUKV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(4-{2-[5-(2-hydroxyethyl)pyridin-2-yl]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-[(4-{2-[5-(2-hydroxyethyl)pyridin-2-yl]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-[5-(2-Hydroxyethyl)-2-pyridinyl]ethoxy]phenyl]methyl]-2,4-thiazolidinedione; Hydroxy Pioglitazone (M-VII)

Database IDs

• CAS Number: 625853-72-7
• PubChem SID: 164227039
• PubChem CID: 71434033

CALCULATED PROPERTIES

• Acid pKa: 6.6480117
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.804293
• LogD (pH = 7.4): 1.3077275
• Log P: 1.9212714
• Molar Refractivity: 99.3195 cm^3
• Polarizability: 38.577698 Å^3
• Polar Surface Area: 88.52 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952060

A novel metabolite of Pioglitazone (P471000).

REFERENCES

• Krieter, P., et al.: Drug Metab. Dispos., 22, 625 (1994)
• Chilcott, J., et al.: Clin. Ther., 23, 1792 (1994)