Rosiglitazone MaleateProduct ingredient for Rosiglitazone
- Name
- Rosiglitazone Maleate
- Drug Entry
- Rosiglitazone
Rosiglitazone is an anti-diabetic drug in the thiazolidinedione class of drugs. It is marketed by the pharmaceutical company GlaxoSmithKline as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Like other thiazolidinediones, the mechanism of action of rosiglitazone is by activation of the intracellular receptor class of the peroxisome proliferator-activated receptors (PPARs), specifically PPARγ. Rosiglitazone is a selective ligand of PPARγ, and has no PPARα-binding action. Apart from its effect on insulin resistance, it appears to have an anti-inflammatory effect: nuclear factor kappa-B (NFκB) levels fall and inhibitor (IκB) levels increase in patients on rosiglitazone. Recent research has suggested that rosiglitazone may also be of benefit to a subset of patients with Alzheimer's disease not expressing the ApoE4 allele. This is the subject of a clinical trial currently underway.
- Accession Number
- DBSALT000153
- Structure
- Synonyms
- Not Available
- UNII
- KX2339DP44
- CAS Number
- 155141-29-0
- Weight
- Average: 473.499
Monoisotopic: 473.125670795 - Chemical Formula
- C22H23N3O7S
- InChI Key
- SUFUKZSWUHZXAV-BTJKTKAUSA-N
- 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-
- IUPAC Name
- (2Z)-but-2-enedioic acid; 4-hydroxy-5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-2,5-dihydro-1,3-thiazol-2-one
- SMILES
- [H]\C(=C(/[H])C(O)=O)C(O)=O.CN(CCOC1=CC=C(CC2SC(=O)N=C2O)C=C1)C1=CC=CC=N1
- External Links
- Predicted Properties
Property Value Source Water Solubility 0.0948 mg/mL ALOGPS logP 2.92 ALOGPS logP 1.8 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 4.03 Chemaxon pKa (Strongest Basic) 6.46 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 75.02 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 98.11 m3·mol-1 Chemaxon Polarizability 37.93 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon