Editing Ciglitazone

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 404168235
| IUPAC_name = 5-{4-[(1-methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione
| image = Ciglitazone.svg
| width = 222

<!--Clinical data-->
| tradename = 
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = 
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 74772-77-3
| ATC_prefix = none
| ATC_suffix = 
| ATC_supplemental = 
| PubChem = 2750
| IUPHAR_ligand = 2711
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB09201
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = U8QXS1WU8G
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D03493
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 7002
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 2648
| smiles = O=C1NC(=O)SC1Cc3ccc(OCC2(C)CCCCC2)cc3
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = YZFWTZACSRHJQD-UHFFFAOYSA-N

<!--Chemical data-->
| chemical_formula = 
| C=18 | H=23 | N=1 | O=3 | S=1 
}}

'''Ciglitazone''' ([[International Nonproprietary Name|INN]]) is a [[thiazolidinedione]]. Developed by [[Takeda Pharmaceuticals]] in the early 1980s, it is considered the prototypical compound for the thiazolidinedione class.<ref>{{cite journal | vauthors = Pershadsingh HA, Szollosi J, Benson S, Hyun WC, Feuerstein BG, Kurtz TW | title = Effects of ciglitazone on blood pressure and intracellular calcium metabolism | journal = Hypertension | volume = 21 | issue = 6 Pt 2 | pages = 1020–1023 | date = June 1993 | pmid = 8505086 | doi = 10.1161/01.hyp.21.6.1020 | doi-access = free }}</ref><ref name=Hulin/><ref>{{cite journal | vauthors = Imoto H, Imamiya E, Momose Y, Sugiyama Y, Kimura H, Sohda T | title = Studies on non-thiazolidinedione antidiabetic agents. 1. Discovery of novel oxyiminoacetic acid derivatives | journal = Chemical & Pharmaceutical Bulletin | volume = 50 | issue = 10 | pages = 1349–1357 | date = October 2002 | pmid = 12372861 | doi = 10.1248/cpb.50.1349 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Sohda T, Kawamatsu Y, Fujita T, Meguro K, Ikeda H | title = [Discovery and development of a new insulin sensitizing agent, pioglitazone] | language = ja | journal = Yakugaku Zasshi | volume = 122 | issue = 11 | pages = 909–918 | date = November 2002 | pmid = 12440149 | doi = 10.1248/yakushi.122.909 | doi-access = free }}</ref>

Ciglitazone was never used as a medication, but it sparked interest in the effects of thiazolidinediones. Several [[analog (chemistry)|analogues]] were later developed, some of which—such as [[pioglitazone]] and [[troglitazone]]—made it to the market.<ref name=Hulin>{{cite journal |vauthors=Hulin B, McCarthy PA, Gibbs EM |title=The glitazone family of antidiabetic agents |journal=Current Pharmaceutical Design |volume=2 |pages=85–102 |year=1996 |doi=10.2174/1381612802666220920215821 |s2cid=252485570 |url=https://books.google.com/books?id=IYn4Va7wtAoC&q=ciglitazone&pg=PA86|url-access=subscription }}</ref>

Ciglitazone significantly decreases [[Vascular endothelial growth factor|VEGF]] production by human [[granulosa cell]]s in an in vitro study, and may potentially be used in [[ovarian hyperstimulation syndrome]].<ref>{{cite journal | vauthors = Shah DK, Menon KM, Cabrera LM, Vahratian A, Kavoussi SK, Lebovic DI | title = Thiazolidinediones decrease vascular endothelial growth factor (VEGF) production by human luteinized granulosa cells in vitro | journal = Fertility and Sterility | volume = 93 | issue = 6 | pages = 2042–2047 | date = April 2010 | pmid = 19342033 | pmc = 2847675 | doi = 10.1016/j.fertnstert.2009.02.059 }}</ref>
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.<ref>{{cite journal | vauthors = Willson TM, Cobb JE, Cowan DJ, Wiethe RW, Correa ID, Prakash SR, Beck KD, Moore LB, Kliewer SA, Lehmann JM | display-authors = 6 | title = The structure-activity relationship between peroxisome proliferator-activated receptor gamma agonism and the antihyperglycemic activity of thiazolidinediones | journal = Journal of Medicinal Chemistry | volume = 39 | issue = 3 | pages = 665–668 | date = February 1996 | pmid = 8576907 | doi = 10.1021/jm950395a }}</ref> Inhibits [[human umbilical vein endothelial cell|HUVEC]] differentiation and angiogenesis and also stimulates adipogenesis and decreases osteoblastogenesis in human mesenchymal stem cells.<ref>{{cite journal | vauthors = Xin X, Yang S, Kowalski J, Gerritsen ME | title = Peroxisome proliferator-activated receptor gamma ligands are potent inhibitors of angiogenesis in vitro and in vivo | journal = The Journal of Biological Chemistry | volume = 274 | issue = 13 | pages = 9116–9121 | date = March 1999 | pmid = 10085162 | doi = 10.1074/jbc.274.13.9116 | doi-access = free }}</ref>

== References ==
{{Reflist}}

{{Oral hypoglycemics}}
{{PPAR modulators}}
{{Xenobiotic-sensing receptor modulators}}

[[Category:Thiazolidinediones]]
[[Category:Phenol ethers]]

{{gastrointestinal-drug-stub}}