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

• ChemBase ID: 166536
• Molecular Formular: C17H17N3O3S
• Molecular Mass: 343.40018
• Monoisotopic Mass: 343.09906242
• SMILES: c1cccnc1NCCOc1ccc(cc1)CC1C(=O)NC(=O)S1
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCNc1ccccn1
• InChI: InChI=1S/C17H17N3O3S/c21-16-14(24-17(22)20-16)11-12-4-6-13(7-5-12)23-10-9-19-15-3-1-2-8-18-15/h1-8,14H,9-11H2,(H,18,19)(H,20,21,22)
• InChIKey: ZJQTVMXUIGXRMR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(4-{2-[(pyridin-2-yl)amino]ethoxy}(^2H₄)phenyl)methyl]-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-({4-[2-(pyridin-2-ylamino)ethoxy](^2H₄)phenyl}methyl)-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-(2-Pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione-d4; SB 237216-d4; N-Desmethyl Rosiglitazone-d4

Database IDs

• PubChem SID: 162260669
• PubChem CID: 46781191

CALCULATED PROPERTIES

• Acid pKa: 6.314843
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.4126642
• LogD (pH = 7.4): 1.5539174
• Log P: 1.7719622
• Molar Refractivity: 93.5551 cm^3
• Polarizability: 35.588882 Å^3
• Polar Surface Area: 80.32 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D292167

A labelled metabolite of Rosiglitazone (R693500).

REFERENCES

• Balton, G.C., et al.: Xenobiotica, 26, 6, 627 (1996)
• Kim, K., et al.: J. Clin. Pharmacol., 45, 941 (1996)
• Kirchheiner, J., et al.: Clin. Pharmacol. Ther., 80, 657 (1996)
• O'Maille, G., et al.: J. Pharm. Biomed. Anal., 48, 934 (1996)