5-({4-[2-(5-ethylpyridin-2-yl)(2H4)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

• ChemBase ID: 176742
• Molecular Formular: C19H20N2O3S
• Molecular Mass: 356.4387
• Monoisotopic Mass: 356.11946351
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)CC
• Canonical SMILES: CCc1ccc(nc1)CCOc1ccc(cc1)CC1SC(=O)NC1=O
• InChI: InChI=1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23)
• InChIKey: HYAFETHFCAUJAY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-({4-[2-(5-ethylpyridin-2-yl)(^2H₄)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-({4-[2-(5-ethylpyridin-2-yl)(^2H₄)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-(5-Ethyl-2-pyridinyl]ethoxy-d4]phenyl]methyl]-2,4-thiazolidinedione; AD-4833-d4; Actos-d4; U-72107A-d4; Pioglitazone-d4

Database IDs

• PubChem SID: 164232652
• PubChem CID: 25235566

CALCULATED PROPERTIES

• Acid pKa: 6.657649
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.1840525
• LogD (pH = 7.4): 2.7427685
• Log P: 3.3282487
• Molar Refractivity: 97.3908 cm^3
• Polarizability: 38.019318 Å^3
• Polar Surface Area: 68.29 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO (hot); THF (hot),
• Apperance: Off-White Solid
• Melting Point: 179-182°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P471002

Labelled Pioglitazone (P471000), which is used as an antidiabetic.A representative lot was 87% d4, 12% d3 no d0.

REFERENCES

• Hofmann, C., et al.: Endocrinology, 129, 1915(1991)
• Kobayashi, M., et al.: Diabetes, 41, 476 (1991)
• Kawaamori, R., et al.,: Diabetes Res. Clin. Pract., 41, 35 (1998)