| Revision as of 13:42, 25 December 2010 editYobot (talk | contribs)Bots4,733,870 editsm WP:CHECKWIKI error fixes + general fixes, References after punctuation per WP:REFPUNC and WP:PAIC using AWB (7505)← Previous edit |
Latest revision as of 09:21, 4 August 2023 edit undoBoghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,800 edits consistent citation formatting |
| (47 intermediate revisions by 24 users not shown) |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
| ⚫ |
| IUPAC_name = 5-{4-benzyl}-1,3-thiazolidine-2,4-dione |
|
|
|
| Watchedfields = changed |
| ⚫ |
| image = Ciglitazone.svg |
|
|
|
| verifiedrevid = 404168235 |
| ⚫ |
| CAS_number = 74772-77-3 |
|
|
⚫ |
| IUPAC_name = 5-{4-benzyl}-1,3-thiazolidine-2,4-dione |
|
| CAS_supplemental = |
|
|
⚫ |
| image = Ciglitazone.svg |
| ⚫ |
| ATC_prefix = none |
|
|
|
| width = 222 |
| ⚫ |
| ATC_suffix = |
|
|
|
|
| ⚫ |
| ATC_supplemental = |
|
|
|
<!--Clinical data--> |
| ⚫ |
| PubChem = 2750 |
|
|
| DrugBank = |
|
| tradename = |
|
⚫ |
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
| ⚫ |
| KEGG = D03493 |
|
|
⚫ |
| pregnancy_US = <!-- A / B / C / D / X --> |
| ⚫ |
| chemical_formula = |
|
|
⚫ |
| pregnancy_category = |
| ⚫ |
| C=18 | H=23 | N=1 | O=3 | S=1 |
|
|
⚫ |
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> |
|
| molecular_weight = 333.44 g/mol |
|
|
⚫ |
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
| ⚫ |
| bioavailability = |
|
|
⚫ |
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
| ⚫ |
| protein_bound = |
|
|
⚫ |
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
| ⚫ |
| metabolism = |
|
|
⚫ |
| legal_status = |
|
⚫ |
| routes_of_administration = |
|
|
|
|
|
<!--Pharmacokinetic data--> |
|
⚫ |
| bioavailability = |
|
⚫ |
| protein_bound = |
|
⚫ |
| metabolism = |
|
| elimination_half-life = |
|
| elimination_half-life = |
|
| excretion = |
|
| excretion = |
|
|
|
| ⚫ |
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
|
|
|
<!--Identifiers--> |
| ⚫ |
| pregnancy_US = <!-- A / B / C / D / X --> |
|
|
|
| CAS_number_Ref = {{cascite|correct|??}} |
| ⚫ |
| pregnancy_category= |
|
|
⚫ |
| CAS_number = 74772-77-3 |
| ⚫ |
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
|
|
⚫ |
| ATC_prefix = none |
| ⚫ |
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
|
|
⚫ |
| ATC_suffix = |
| ⚫ |
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
|
|
⚫ |
| ATC_supplemental = |
| ⚫ |
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
|
|
⚫ |
| PubChem = 2750 |
| ⚫ |
| legal_status = |
|
|
|
| IUPHAR_ligand = 2711 |
| ⚫ |
| routes_of_administration = |
|
|
|
| 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''' (]) is a ]. Developed by ] 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= |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''' (]) is a ]. Developed by ] 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 = | 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 ] were later developed, some of which—such as ] and ]—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 was never used as a medication, but it sparked interest in the effects of thiazolidinediones. Several ] were later developed, some of which—such as ] and ]—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}}</ref> |
| ⚫ |
Ciglitazone significantly decreases ] production by human ]s in an in vitro study, and may potentially be used in ].<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)</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)</ref> |
|
|
|
|
|
|
⚫ |
Ciglitazone significantly decreases ] production by human ]s in an in vitro study, and may potentially be used in ].<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> |
| ⚫ |
==References== |
|
|
⚫ |
Ciglitazone is a potent and selective ] ligand. It binds to the PPARγ ligand-binding domain with an ] 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 ] 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}} |
|
{{Reflist}} |
|
|
|
|
|
{{Oral hypoglycemics}} |
|
|
{{PPAR modulators}} |
|
|
{{Xenobiotic-sensing receptor modulators}} |
|
|
|
|
|
] |
|
] |
|
] |
|
] |
|
|
|
|
|
|
{{gastrointestinal-drug-stub}} |
|
|
|
|
{{pharma-stub}} |
|