From Wikipedia, the free encyclopedia
Chemical compound
Ciglitazone
ATC code
5-{4-[(1-methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione
CAS Number
PubChem
CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (
EPA )
ECHA InfoCard
100.220.474
Formula C 18 H 23 N O 3 S
Molar mass 333.45 g·mol−1 3D model (
JSmol )
O=C1NC(=O)SC1Cc3ccc(OCC2(C)CCCCC2)cc3
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
N Y
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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 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]
References
^ Pershadsingh HA, Szollosi J, Benson S, Hyun WC, Feuerstein BG, Kurtz TW (June 1993).
"Effects of ciglitazone on blood pressure and intracellular calcium metabolism" . Hypertension . 21 (6 Pt 2): 1020–1023.
doi :
10.1161/01.hyp.21.6.1020 .
PMID
8505086 .
^
a
b Hulin B, McCarthy PA, Gibbs EM (1996).
"The glitazone family of antidiabetic agents" . Current Pharmaceutical Design . 2 : 85–102.
doi :
10.2174/1381612802666220920215821 .
S2CID
252485570 .
^ Imoto H, Imamiya E, Momose Y, Sugiyama Y, Kimura H, Sohda T (October 2002).
"Studies on non-thiazolidinedione antidiabetic agents. 1. Discovery of novel oxyiminoacetic acid derivatives" . Chemical & Pharmaceutical Bulletin . 50 (10): 1349–1357.
doi :
10.1248/cpb.50.1349 .
PMID
12372861 .
^ Sohda T, Kawamatsu Y, Fujita T, Meguro K, Ikeda H (November 2002).
"[Discovery and development of a new insulin sensitizing agent, pioglitazone]" . Yakugaku Zasshi (in Japanese). 122 (11): 909–918.
doi :
10.1248/yakushi.122.909 .
PMID
12440149 .
^ Shah DK, Menon KM, Cabrera LM, Vahratian A, Kavoussi SK, Lebovic DI (April 2010).
"Thiazolidinediones decrease vascular endothelial growth factor (VEGF) production by human luteinized granulosa cells in vitro" . Fertility and Sterility . 93 (6): 2042–2047.
doi :
10.1016/j.fertnstert.2009.02.059 .
PMC
2847675 .
PMID
19342033 .
^ Willson TM, Cobb JE, Cowan DJ, Wiethe RW, Correa ID, Prakash SR, et al. (February 1996). "The structure-activity relationship between peroxisome proliferator-activated receptor gamma agonism and the antihyperglycemic activity of thiazolidinediones". Journal of Medicinal Chemistry . 39 (3): 665–668.
doi :
10.1021/jm950395a .
PMID
8576907 .
^ Xin X, Yang S, Kowalski J, Gerritsen ME (March 1999).
"Peroxisome proliferator-activated receptor gamma ligands are potent inhibitors of angiogenesis in vitro and in vivo" . The Journal of Biological Chemistry . 274 (13): 9116–9121.
doi :
10.1074/jbc.274.13.9116 .
PMID
10085162 .
fast-acting short-acting long-acting ultra-long-acting
inhalable
PPARα Tooltip Peroxisome proliferator-activated receptor alpha
PPARδ Tooltip Peroxisome proliferator-activated receptor delta
PPARγ Tooltip Peroxisome proliferator-activated receptor gamma Non-selective
CAR Tooltip Constitutive androstane receptor
PXR Tooltip Pregnane X receptor