troglitazone   Click here for help

GtoPdb Ligand ID: 2693

Synonyms: CS-045 | Rezulin®
Approved drug
troglitazone is an approved drug (FDA (1997))
Compound class: Synthetic organic
Comment: Troglitazone is an antidiabetic and anti-inflammatory drug.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 110.16
Molecular weight 441.16
XLogP 3.6
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES O=C1NC(=O)C(S1)Cc1ccc(cc1)OCC1(C)CCc2c(O1)c(C)c(c(c2C)O)C
Isomeric SMILES O=C1NC(=O)C(S1)Cc1ccc(cc1)OCC1(C)CCc2c(O1)c(C)c(c(c2C)O)C
InChI InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)
InChI Key GXPHKUHSUJUWKP-UHFFFAOYSA-N
References
1. Berger J, Bailey P, Biswas C, Cullinan CA, Doebber TW, Hayes NS, Saperstein R, Smith RG, Leibowitz MD. (1996)
Thiazolidinediones produce a conformational change in peroxisomal proliferator-activated receptor-gamma: binding and activation correlate with antidiabetic actions in db/db mice.
Endocrinology, 137 (10): 4189-95. [PMID:8828476]
2. Henke BR, Blanchard SG, Brackeen MF, Brown KK, Cobb JE, Collins JL, Harrington WW, Hashim MA, Hull-Ryde EA, Kaldor I, Kliewer SA, Lake DH, Leesnitzer LM, Lehmann JM, Lenhard JM, Orband-Miller LA, Miller JF, Mook RA, Noble SA, Oliver W, Parks DJ, Plunket KD, Szewczyk JR, Willson TM. (1998)
N-(2-Benzoylphenyl)-L-tyrosine PPARgamma agonists. 1. Discovery of a novel series of potent antihyperglycemic and antihyperlipidemic agents.
J Med Chem, 41 (25): 5020-36. [PMID:9836620]
3. Young PW, Buckle DR, Cantello BC, Chapman H, Clapham JC, Coyle PJ, Haigh D, Hindley RM, Holder JC, Kallender H, Latter AJ, Lawrie KW, Mossakowska D, Murphy GJ, Roxbee Cox L, Smith SA. (1998)
Identification of high-affinity binding sites for the insulin sensitizer rosiglitazone (BRL-49653) in rodent and human adipocytes using a radioiodinated ligand for peroxisomal proliferator-activated receptor gamma.
J Pharmacol Exp Ther, 284 (2): 751-9. [PMID:9454824]