Ciglitazone

Ciglitazone
Ciglitazone
Systematic (IUPAC) name
5-{4-[(1-methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 74772-77-3 YesY
ATC code None
PubChem CID 2750
UNII U8QXS1WU8G N
KEGG D03493 YesY
ChEMBL CHEMBL7002 N
Chemical data
Formula C18H23NO3S 
Mol. mass 333.44 g/mol
 N(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.[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

  1. ^ 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): 1020–3. PMID 8505086. 
  2. ^ a b Hulin B, McCarthy PA, Gibbs EM (1996). "The glitazone family of antidiabetic agents". Current Pharmaceutical Design 2: 85–102. http://books.google.com/?id=IYn4Va7wtAoC&pg=PA86&dq=ciglitazone. 
  3. ^ 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". Chem. Pharm. Bull. 50 (10): 1349–57. doi:10.1248/cpb.50.1349. PMID 12372861. 
  4. ^ Sohda T, Kawamatsu Y, Fujita T, Meguro K, Ikeda H (November 2002). "[Discovery and development of a new insulin sensitizing agent, pioglitazone"] (in Japanese). Yakugaku Zasshi 122 (11): 909–18. doi:10.1248/yakushi.122.909. PMID 12440149. http://www.jstage.jst.go.jp/article/yakushi/122/11/909/_pdf. 
  5. ^ 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". Fertil. Steril. 93 (6): 2042–7. doi:10.1016/j.fertnstert.2009.02.059. PMC 2847675. PMID 19342033. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2847675. 
  6. ^ Willson, T.M., Cobb, J.E., Cowan, D.J., et al. The structure-activity relationship between peroxisome proliferator-activated receptor γ agonism and the antihyperglycemic activity of thiazolidinediones. J Med Chem 39 665-668 (1996)[1]
  7. ^ X. Xin, et al. Peroxisome proliferator-activated receptor gamma ligands are potent inhibitors of angiogenesis in vitro and in vivo; J. Biol. Chem. 274, 9116 (1999)[2]


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