Ciglitazone: Difference between revisions

| IUPAC_name = 5-{4-[(1-methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione

| image = Ciglitazone.svg

| CAS_number = 74772-77-3

| CAS_supplemental =

| ATC_prefix = none

| ATC_suffix =

| ATC_supplemental =

| PubChem = 2750

| DrugBank =

| KEGG = D03493

| chemical_formula =

| C=18 | H=23 | N=1 | O=3 | S=1

| molecular_weight = 333.44 g/mol

| bioavailability =

| protein_bound =

| metabolism =

| excretion =

| 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 =

'''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 |author=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=1020–3 |year=1993 |month=June |pmid=8505086 |doi= |url=}}</ref><ref name=Hulin/><ref>{{cite journal |author=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=Chem. Pharm. Bull. |volume=50 |issue=10 |pages=1349–57 |year=2002 |month=October |pmid=12372861 |doi=10.1248/cpb.50.1349}}</ref><ref>{{cite journal |author=Sohda T, Kawamatsu Y, Fujita T, Meguro K, Ikeda H |title=[Discovery and development of a new insulin sensitizing agent, pioglitazone] |language=Japanese |journal=Yakugaku Zasshi |volume=122 |issue=11 |pages=909–18 |year=2002 |month=November |pmid=12440149 |doi= 10.1248/yakushi.122.909|url=http://www.jstage.jst.go.jp/article/yakushi/122/11/909/_pdf}}</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 |author=Hulin B, McCarthy PA, Gibbs EM |title=The glitazone family of antidiabetic agents |journal=Current Pharmaceutical Design |volume=2 |pages=85–102 |year=1996 |url=http://books.google.com/?id=IYn4Va7wtAoC&pg=PA86&dq=ciglitazone}}</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 |author=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=Fertil. Steril. |volume=93 |issue=6 |pages=2042–7 |year=2010 |month=April |pmid=19342033 |pmc=2847675 |doi=10.1016/j.fertnstert.2009.02.059 |url=}}</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>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)[http://pubs.acs.org/doi/pdf/10.1021/jm950395a?cookieSet=1]</ref> Inhibits HUVEC differentiation and angiogenesis and also stimulates adipogenesis and decreases osteoblastogenesis in human mesenchymal stem cells.<ref>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)[http://www.ncbi.nlm.nih.gov/pubmed/10085162?dopt=Citation]</ref>

==References==

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