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
PubChem Compound
5281055
ChemSpider
4444514
ChEBI
8892
ChEMBL
CHEMBL843
Predicted Properties
PropertyValueSource
Water Solubility0.0948 mg/mLALOGPS
logP2.92ALOGPS
logP1.8Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.03Chemaxon
pKa (Strongest Basic)6.46Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area75.02 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity98.11 m3·mol-1Chemaxon
Polarizability37.93 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon