Rosiglitazone Enantiomers Structural Formulae

Rosiglitazone is an anti-diabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approx $2.5bn in 2006, but declined after reports of adverse effects. The drugs patent expires in 2012.

Some reports have suggested that rosiglitazone is associated with a statistically significant risk of heart attacks, but other reports have disagreed, and the controversy has not been resolved. Concern about adverse effects has reduced the use of rosiglitazone despite its sustained effects on glycemic control.

The drug was controversial in the U.S. Food and Drug Administration. Some reviewers concluded that rosiglitazone caused more deaths than pioglitazone (Actos) and recommended that rosiglitazone be taken off the market, but an F.D.A. panel disagreed and it remains on the market in the U.S.