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Thiazolidinediones

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Definition: THIAZOLES with two keto oxygens. Members are insulin-sensitizing agents which overcome INSULIN RESISTANCE by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).      Other names Glitazones
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
TD49 thiazolidinedione  0   *Thiazolidinediones. Environ Toxicol Chem. 2011 Dec;30(12):2810-6
5-(4-hydroxy-3,5-dimethylbenzylidene)thiazolidine-2,4-dione  0   *Benzylidene Compounds *Thiazolidinediones. Curr Neurovasc Res. 2011 Feb;8(1):25-34.
5-acridin-9-ylmethylene-3-(4-methyl-benzyl)-thiazolidine-2,4-dione  0   *Acridines *Thiazolidinediones. Eur J Med Chem. 2011 Sep;46(9):4245-51.
5-(4-(cyclopentylmethoxy)benzylidene)thiazolidine-2,4-dione  0   *Thiazolidinediones. Int J Pharm 2011 Feb 28;405(1-2):137-41
4-(4-fluorobenzyl)-2-p-tolyl-1,2,4-thiadiazolidine-3,5-dione  0   *Thiazolidinediones. Biochemistry 2011 Apr 19;50(15):3181-92
3-benzyl-2-(4-fluorophenyl)-1,3-thiazolidin-4-one  0   *Thiazolidinediones. Acta Crystallogr C. 2011 Jan;67(Pt 1):o10-2
2-(3-((4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenylamino)methyl)benzamido)pentanedioic acid  0   *Thiazolidinediones Glutamic Acid/*analogs & derivatives. J Med Chem 2010 Sep 23;53(18):6584-94
troglitazone sulfate  0   *Sulfuric Acid Esters *Thiazolidinediones. Drug Metab Dispos 2007 Feb;35(2):209-14
N-(4-(3-(1-methyl-cyclohexylmethyl)-2,4-dioxothiazolidin-5-ylidenemethyl)phenyl)-4-nitro-3-trifluoromethylbenzenesulfonamide  0   *Sulfonamides *Thiazolidinediones. J Med Chem 2010 Mar 25;53(6):2552-61
N-((4-(biphenyl-2-ylmethoxy)-1-(2-(4-fluorobenzoyl)benzoyl)pyrrolidin-2-yl)methyl)-4-((2,4-dioxothiazolidin-5-ylidene)methyl)benzamide  0   *Pyrrolidines *Thiazolidinediones Group IV Phospholipases A2/antagonists & inhibitors. Inflamm Res 2010 Jan;59(1):53-62
5-(4-methoxybenzylidene)thiazolidine-2,4-dione  0   *Thiazolidinediones. J Med Chem 2010 Jan 14;53(1):273-81
lobeglitazone  0   *Pyrimidines *Thiazolidinediones PPAR alpha/agonists PPAR gamma/agonists. J Pharm Biomed Anal 2009 Dec 5;50(5):872-7
3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione  0   *Thiazolidinediones. Bioorg Med Chem Lett 2009 Nov 1;19(21):6042-6
BLX 1002  0   *Thiazolidinediones. Am J Physiol Cell Physiol 2009 Feb;296(2):C346-54
5-(4-hydroxy-3-trifluoromethylbenzylidene)-3-(1-methylcyclohexyl)thiazolidine-2,4-dione  0   *Thiazolidinediones. Mol Pharmacol 2009 Jul;76(1):47-57
3-(3,5-dichlorophenyl)-2,4-thiazolidinedione  0   *Thiazolidinediones. Toxicology 2008 Sep 4;250(2-3):100-8
R 147176  0   *Imidazoles *Thiazolidinediones. Arterioscler Thromb Vasc Biol 2008 Oct;28(10):1767-73
4-((5-bromo-4-((2,4-dioxo-3-(2-oxo-2-phenylethyl)-1,3-thiazolidin-5-ylidene)methyl)-2-ethoxyphenoxy)methyl)benzoic acid  0   *Benzoic Acids *Thiazolidinediones. Biochem Biophys Res Commun 2008 Oct 10;375(1):139-44
3-(3,4-dichlorobenzyl)-5-(3,4,5-trihydroxybenzylidene)thiazolidine-2,4-dione  0   *Thiazolidinediones. Exper Opin Ther Targets 2008 Jul;12(7):783-94
N-(-4-(N-(biphenyl-2-ylmethyl)-N-2-methylpropylamino)- 1-(2-(2,4-difluorobenzoyl)benzoyl)pyrrolidin- 2-yl)methyl-3-(4-(2,4-dioxothiazolidin-5-ylidenemethyl) phenyl)acrylamide  0   *Acrylamides *Thiazolidinediones Group IV Phospholipases A2/antagonists & inhibitors. Pharmacology 2008;81(4):301-11
rivoglitazone  0   *Thiazolidinediones. Curr Opin Investig Drugs 2007 Apr;8(4):338-44
SB-271258  0   *Thiazolidinediones. Toxicol In Vitro 2006 Sep;20(6):808-15
N-(2-(4-((2,4-dioxo-1,3-thiazolidin-5-yl)methyl)phenoxy)ethyl)-5-(1,2-dithiolan-3-yl)-N-methylpentanamide  0   *Thiazolidinediones Thioctic Acid/*analogs & derivatives PPAR gamma/agonists. J Med Chem 2006 Jul 13;49(14):4072-84
5-(4-((6-(allyloxy)-2,5,7,8-tetramethylchroman-2-yl)methoxy)-3-methoxybenzylidene)thiazolidine-2,4-dione  0   *Benzopyrans *Thiazolidinediones. J Med Chem 2006 Jul 27;49(15):4684-9
5-(5-(4-fluoro-2-hydroxyphenyl)furan-2-ylmethylene)thiazolidine-2,4-dione  0   *Thiazolidinediones Phosphatidylinositol 3-Kinases/antagonists & inhibitors. J Med Chem 2006 Jun 29;49(13):3857-71
5-((4-(2-(5-methyl-2-phenyl-oxazol-4-yl)ethoxy)benzo(2) thiophen-7-yl)methyl)-thiazolidine-2,4-dione  0   *Thiophenes *Thiazolidinediones. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 May 1;835(1-2):40-6
M-IV compound  0   *Thiazolidinediones. Br J Clin Pharmacol. 2006 Jan;61(1):70-8
M-II compound  0   *Thiazolidinediones. Br J Clin Pharmacol. 2006 Jan;61(1):70-8
RS 5444  0   *Thiazolidinediones. Oncogene. 2006 Apr 13;25(16):2304-17
3-benzyl-5-acridinylidene-thiazolidine-2,4-dione  0   *Acridines *Benzyl Compounds *Thiazolidinediones. Eur J Med Chem. 2005 Nov;40(11):1129-33
5-benzylidene-3-(4-methyl-benzyl)-thiazolidine-2,4-dione  0   *Benzyl Compounds *Thiazolidinediones. Eur J Med Chem. 2005 Nov;40(11):1129-33
5-adamantylpentanoic acid (2-(4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxy)ethyl)(methyl)amide  0   *Thiazolidinediones Adamantane/*analogs & derivatives. J Pharmacol Exp Ther 2005 Dec;315(3):996-1004
5-(3,5-di-tert-butyl-4-hydroxybenzylidene)thiazolidine-2,4-dione  0   *Thiazolidinediones. Mol Cell Endocrinol 2005 Oct 20;242(1-2):96-102
5-(2,2-difluorobenzo(1,3)dioxol-5-ylmethylene)thiazolidine-2,4-dione  0   *Dioxoles *Thiazolidinediones Phosphatidylinositol 3-Kinases/antagonists & inhibitors. Nat Med 2005 Sep;11(9):936-43
5-quinoxalin-6-ylmethylenethiazolidine-2,4-dione  0   *Quinoxalines *Thiazolidinediones Phosphatidylinositol 3-Kinases/antagonists & inhibitors. Nat Med 2005 Sep;11(9):936-43
5-(3-methoxyphenylidene)-2-phenylimino-3-propyl-4-thiazolidinone  0   *Thiazolidinediones. Bioorg Med Chem. 2005 Jul 1;13(13):4243-52
thiazolidine-2,4-thione  0   *Thiones *Thiazolidinediones. Bioorg Med Chem Lett. 2004 Nov 1;14(21):5401-5
thiazolidine-2,4-dione  0   *Thiazolidinediones. Bioorg Med Chem Lett. 2004 Nov 1;14(21):5401-5
balaglitazone  0   *Quinazolines *Thiazolidinediones Hypoglycemic Agents. J Chromatogr A. 2004 Sep 17;1049(1-2):183-87
DRF 2519  0   *Thiazolidinediones. Eur J Pharmacol 2004 May 3;491(2-3):195-206
5-(3-(3-(4-phenoxy-2-propylphenoxy)propoxy)phenyl)-2,4-thiazolidinedione  0   *Phenyl Ethers *Thiazolidinediones. Endocrinology 2004 Apr;145(4):1640-8
NIP-222  0   *Thiazolidinediones. Metabolism 2003 Dec;52(12):1633-7
N-desmethylrosiglitazone  0   *Thiazolidinediones. Diabetologia 2003 Oct;46(10):1319-23
5-(4-(2-(2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl)ethoxy)phenylmethyl)thiazolidine-2,4-dione  0   *Pyrimidines *Thiazolidinediones. Diabetes Obes Metab 2002 Sep;4(5):319-28
5-(4-(cyclohexylethoxy)benzylidene)-2,4-thiazolidinedione  0   *Thiazolidinediones. Arch Biochem Biophys 2002 Sep 15;405(2):247-51
5-(4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl)-2,4-dioxothiazollidine, troglitazone dihydrate  0   *Chromans *Thiazolidinediones. Anal Sci 2001 Mar;17(3):467-8
5-(4-(N-(2-pyridyl)-(2S)-pyrrolidine-2-methoxy)phenylmethylene) thiazolidine-2,6-dione  0   *Pyrrolidines *Thiazolidinediones. Metabolism. 2000 Nov;49(11):1417-24
5-(4-(5-methoxy-3-methyl-3H-imidazo(4,5-b)pyridin-2-ylmethoxy)benzyl)thiazolidine-2,4-dione  0   *Imidazoles *Thiazolidinediones. J Med Chem 2000 Aug 10;43(16):3052-66
1,13a-dihydro-3H,5H,13H-naphtho(2,3-f)thiazolo(4,3-c)(1,4)thiazepine-5,13-dione  0   *Thiazepines *Thiazolidinediones. J Med Chen 1999 Aug 26;42(17):3334-41
2,3-dihydro-5H-naphtho(2,3-f)thiazolo(2,3-c)(1,4)thiazepine-5,13(1aH)-dione  0   *Thiazepines *Thiazolidinediones. J Med Chem 1999 Aaug 26;42(17):3334-41
5-(4-((1-(pyridin-2-yl)pyrrolidin-2-yl)methoxy)phenylmethylene)thiazolidine-2,4-dione  0   *Pyridines *Thiazolidinediones. J Med Chem 1999 Jul 15;42(14):2569-81
netoglitazone  161600-01-7   *Thiazolidinediones. Endocrinology 1998 Nov;139(11):4531-9
DN 108  195604-21-8   *Thiazolidinediones. Arzneimittelforschung 1998 Jum;48(6):651-7
5-((4-(2-(1-indolyl)ethoxy)-phenyl)methyl)thiazolidine-2,4-dione  0   *Indoles *Thiazolidinediones. J Med Chem 1998 May 7;41(10):1619-30
5-((2-(2-naphthalenylmethyl)-5-benzoxazolyl)methyl)-2,4-thiazolidinedione  118384-10-4   *Benzoxazoles *Thiazolidinediones. Biol Pharm Bull 1997 Apr;20(4):460-3
1,2,4-dithiazolidine-3,5-dione  0   *Thiazolidinediones. Nucleic Acids Res 1996 May 1;24(9):1602-7
BM 131246  0   *Oxazoles *Thiazolidinediones. Arzneimittelforschung 1995 Dec;45(12):1284-8
BM 501050  0   *Naphthalenes *Thiazolidinediones. Arzneimittelforschung 1995 Dec;45(12):1284-8
darglitazone  141200-24-0 2,4-Thiazolidinedione, 5-((4-(3-(5-methyl-2-phenyl-4-oxazolyl)-1-oxopropyl)phenyl)methyl)-, (+-)  *Thiazolidinediones. J Biol Chem 1994 Oct 14;269(41):25735-41
AD 5075  103788-05-2 2,4-Thiazolidinedione, 5-((4-(2-hydroxy-2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy)phenyl)methyl)  *Thiazolidinediones. J Biol Chem 1994 Oct 14;269(41):25735-41
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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012
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