(2Z)-but-2-enedioic acid; 5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione

• ChemBase ID: 73051
• Molecular Formular: C22H23N3O7S
• Molecular Mass: 473.49892
• Monoisotopic Mass: 473.12567109
• SMILES: c1cccc(n1)N(CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)C.C(=O)(/C=C\C(=O)O)O
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCN(c1ccccn1)C.OC(=O)/C=C\C(=O)O
• InChI: InChI=1S/C18H19N3O3S.C4H4O4/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15;5-3(6)1-2-4(7)8/h2-9,15H,10-12H2,1H3,(H,20,22,23);1-2H,(H,5,6)(H,7,8)/b;2-1-
• InChIKey: SUFUKZSWUHZXAV-BTJKTKAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; 5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: maleic acid; rosiglitazone
• Synonyms: Rosiglitazone maleate; 5-(4-(2-(methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione maleate; 5-[[4-[2-(Methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione (2Z)-2-Butenedioate; Avandia; BRL-49653c; Rosiglitazone Maleate

Database IDs

• CAS Number: 155141-29-0
• PubChem SID: 162037971
• PubChem CID: 5281055

CALCULATED PROPERTIES

• Acid pKa: 6.844312
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.151827
• LogD (pH = 7.4): 2.2077625
• Log P: 2.446348
• Molar Refractivity: 97.7899 cm^3
• Polarizability: 37.403675 Å^3
• Polar Surface Area: 71.53 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water (pH 2.3)
• Apperance: White To Off-White Solid
• Melting Point: 122-123°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Product Information

• Salt Data: maleate; Maleate

DETAILS

Selleck Chemicals - S2505

Research Area: Cardiovascular Disease
Biological Activity:
Rosiglitazone maleate (Avandia) is an anti-diabetic agent in the thiazolidinedione class of agents. Rosiglitazone maleate (Avandia) acts primarily by increasing insulin sensitivity. Rosiglitazone maleate (Avandia) improves glycemic control while reducing circulating insulin levels. Rosiglitazone is a member of the thiazolidinedione class of agents. They reduce glucose, fatty acid, and insulin blood concentrations. They work by binding to the peroxisome proliferator-activated receptors (PPARs). Thiazolidinediones enter the cell, bind to the nuclear receptors, and affect the expression of DNA. Rosiglitazone maleate (Avandia) also appears to have an anti-inflammatory effect in addition to its effect on insulin resistance. [1]

Toronto Research Chemicals - R693500

Insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR- γ).

REFERENCES

• http://en.wikipedia.org/wiki/Rosiglitazone
• Cantello, B.C.C., et al.: J. Med. Chem., 37, 3977 (1994)
• Oakes, N.D., et al.: Diabetes, 43, 1203 (1994)
• Balton, G.C., et al.: Xenobiotica, 26, 627 (1994)
• Barman, J.A., et al.: Drugs, 57, 921 (1994)