Structure via PubChem · Public domain (PubChem)
(RS)-rosiglitazone
Sign in to saveAlso known as rosiglizole, BRL-49653, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione, (±)-5-[p-[2-(methyl-2-pyridylamino)ethoxy]benzyl]-2,4-thiazolidinedione, (RS)-5-{4-[2-(methyl-2-pyridylamino)ethoxy]benzyl}-2,4-thiazolidinedion, rosiglitazone
Rosiglitazone (trade name Avandia) is an antidiabetic drug in the thiazolidinedione class. It works as an insulin sensitizer, by binding to the PPAR in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug or for use in combination with metformin or with glimepiride. First released in 1999, annual sales peaked at approximately $2.5 billion in 2006; however, following a meta-analysis in 2007 that linked the drug's use to an increased risk of heart attack, sales plummeted to just $9.5 million in 2012. T
Chemical data
- Formula
- C18H19N3O3S
- Molecular weight
- 357.4 g/mol
- IUPAC name
- 5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
- SMILES
- CN(CCOC1=CC=C(C=C1)CC2C(=O)NC(=O)S2)C3=CC=CC=N3
- InChIKey
- YASAKCUCGLMORW-UHFFFAOYSA-N
- XLogP
- 3.1
- Polar surface area
- 96.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1999
- Admin. routes
- oral
- Indications
- diabetes mellitus, erectile dysfunction, focal segmental glomerulosclerosis, Cognitive impairment
via ChEMBL · EBI
Research
29 papers- Neutrophils in Acute Stroke Pathophysiology.Stroke · 2019
- Selective Lipolysis by Photoactivation of Chaperone-Mediated Autophagy Using Adipocyte Membrane-Coated Nanoparticle in Hydrogel.Advanced materials (Deerfield Beach, Fla.) · 2025
- A novel dual-targeted rosiglitazone-loaded nanoparticle for the prevention of diet-induced obesity via the browning of white adipose tissue.Journal of controlled release : official journal of the Controlled Release Society · 2021
- Thiazolidinediones improve flow-mediated dilation: a meta-analysis of randomized clinical trials.European journal of clinical pharmacology · 2016
- Electrophilic nitro-oleic acid reverses obesity-induced hepatic steatosis.Redox biology · 2019
via PubMed
Wikidata facts
- Subclass of
- glitazone
- Has part
- carbon
- Mass
- 357.114712
- Has use
- medication
Show 7 more facts
- chemical formula
- C₁₈H₁₉N₃O₃S
- Commons category
- Rosiglitazone
- canonical SMILES
- CN(CCOC1=CC=C(C=C1)CC2C(=O)NC(=O)S2)C3=CC=CC=N3
- World Health Organisation international non-proprietary name
- rosiglitazone
- defined daily dose
- 6
- subject has role
- anti-diabetic medication
- found in taxon
- Exophiala
Sources (6)
via Wikidata · CC0
~24 min read
Encyclopedic overview
26 sectionsContents
- Medical uses
- Adverse effects
- Heart failure
- Heart attacks
- Death
- Stroke
- Bone fractures
- Hypoglycaemia
- Weight gain
- Eye damage
- Hepatotoxicity
- Contraindications
- Pharmacology
- History
- Society and culture
- Sales
- Lawsuits
- United States investigations
- European investigations
- New Zealand
- South Africa
- Controversy and response
- Research
- Synthesis
- References
- External links
Rosiglitazone (trade name Avandia) is an antidiabetic drug in the thiazolidinedione class. It works as an insulin sensitizer, by binding to the PPAR in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug or for use in combination with metformin or with glimepiride. First released in 1999, annual sales peaked at approximately $2.5 billion in 2006; however, following a meta-analysis in 2007 that linked the drug's use to an increased risk of heart attack, sales plummeted to just $9.5 million in 2012. The drug's patent expired in 2012.
It was patented in 1987 and approved for medical use in 1999. Despite rosiglitazone's effectiveness at decreasing blood sugar in type 2 diabetes mellitus, its use decreased dramatically as studies showed apparent associations with increased risks of heart attacks and death. Adverse effects alleged to be caused by rosiglitazone were the subject of over 13,000 lawsuits against GSK; as of July 2010, GSK had agreed to settlements on more than 11,500 of these suits.
Excerpted from Wikipedia’s “(RS)-rosiglitazone” article, available under the CC BY-SA 4.0 licence.