Article: Rosiglitazone

Rosiglitazone
Systematic (IUPAC) name
5-((4-(2-(methyl-2-pyridinylamino) ethoxy)phenyl)methyl)- 2,4-thiazolidinedione
Identifiers
CAS number	122320-73-4
ATC code	A10BG02
PubChem	77999
DrugBank	APRD00403
Chemical data
Formula	C18H19N3O3S
Mol. weight	357.428 g/mol
Pharmacokinetic data
Bioavailability	99%
Protein binding	99.8%
Metabolism	Hepatic (CYP2C8-mediated)
Half life	3-4 hours
Excretion	Renal (64%) and fecal (23%)
Therapeutic considerations
Pregnancy cat.	B3(AU) C(US)
Legal status	POM(UK) ℞-only(US)
Routes	Oral

Rosiglitazone is an anti-diabetic drug from the thiazolidinedione class. It is being marketed as Avandia® by the pharmaceutical company GlaxoSmithKline, both as a standalone preparation and in combination with metformin (Avandamet®). Another combination drug approved by the FDA is Avandaryl® (with glimepiride).

Like other thiazolidinediones, its mechanism of action is by activation of the intracellular receptor class of the peroxisome proliferator-activated receptors (PPARs), specifically PPARγ. Rosiglitazone is a pure 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 (Mohanty et al).