Basic Information
ID DDInter1621
Drug Type small molecule
Molecular Formula C18H19N3O3S
Molecular Weight 357.427
CAS Number 122320-73-4
Description 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.
ATC Classification A10BD04 A10BG02 A10BD03
IUPAC Name 5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
InChI YASAKCUCGLMORW-UHFFFAOYSA-N
Canonical SMILES CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1
Useful Links DrugBank ChEBI PubChem Substance KEGG Drug ChemSpider BindingDB PharmGKB Therapeutic Targets Database Guide to Pharmacology Wikipedia ChEMBL
Interactions with Rosiglitazone
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Multi-DRUG trade Multi-DRUG Drug type Warning Note