Ciglitazone

Ciglitazone (INN) is a thiazolidinedione. Developed by Takeda Pharmaceuticals in the early 1980s, it is considered the prototypical compound for the thiazolidinedione class.^[1][2][3][4]

Ciglitazone

Clinical data
ATC code	none
Identifiers
IUPAC name 5-{4-[(1-methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione
CAS Number	74772-77-3 Y
PubChem CID	2750
IUPHAR/BPS	2711
DrugBank	DB09201 Y
ChemSpider	2648 N
UNII	U8QXS1WU8G
KEGG	D03493 Y
ChEMBL	ChEMBL7002 N
CompTox Dashboard (EPA)	DTXSID0040757
ECHA InfoCard	100.220.474
Chemical and physical data
Formula	C18H23NO3S
Molar mass	333.45 g·mol−1
3D model (JSmol)	Interactive image
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 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.^[2]

Ciglitazone significantly decreases VEGF production by human granulosa cells in an in vitro study, and may potentially be used in ovarian hyperstimulation syndrome.^[5] 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.^[6] Inhibits HUVEC differentiation and angiogenesis and also stimulates adipogenesis and decreases osteoblastogenesis in human mesenchymal stem cells.^[7]