Ciglitazone

Ciglitazone

Systematic (IUPAC) name
5-{4-[(1-methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione
Identifiers
CAS Number	74772-77-3 Y
ATC code	none
PubChem	CID: 2750
IUPHAR/BPS	2711
ChemSpider	2648 N
UNII	U8QXS1WU8G N
KEGG	D03493 Y
ChEMBL	CHEMBL7002 N
Chemical data
Formula	C18H23NO3S
Molecular mass	333.44 g/mol
SMILES O=C1NC(=O)SC1Cc3ccc(OCC2(C)CCCCC2)cc3
InChI InChI=1S/C18H23NO3S/c1-18(9-3-2-4-10-18)12-22-14-7-5-13(6-8-14)11-15-16(20)19-17(21)23-15/h5-8,15H,2-4,9-12H2,1H3,(H,19,20,21) N Key:YZFWTZACSRHJQD-UHFFFAOYSA-N N
NY (what is this?)  (verify)

Ciglitazone (INN) is a thiazolidinedione. Developed by Takeda Pharmaceuticals in the early 1980s, it is considered the prototypical compound for the thiazolidinedione class.

Ciglitazone was never used as a medication, but it sparked interest in the effects of thiazolidinediones. Several analogues were later developed, some of which—such as pioglitazone and troglitazone—made it to the market.

Ciglitazone significantly decreases VEGF production by human granulosa cells in an in vitro study, and may potentially be used in ovarian hyperstimulation syndrome. Ciglitazone is a potent and selective PPARγ ligand. It binds to the PPARγ ligand-binding domain with an EC50 of 3.0 µM. Ciglitazone is active in vivo as an anti-hyperglycemic agent in the ob/ob murine model. Inhibits HUVEC differentiation and angiogenesis and also stimulates adipogenesis and decreases osteoblastogenesis in human mesenchymal stem cells.