rosiglitazone   Click here for help

GtoPdb Ligand ID: 1056

Synonyms: Avandia® | rosiglizole
Approved drug
rosiglitazone is an approved drug (FDA (1999), EMA (2000))
Compound class: Synthetic organic
Comment: Marketed formulations may contain rosiglitazone maleate (PubChem CID 5281055).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 96.83
Molecular weight 357.11
XLogP 2.44
No. Lipinski's rules broken 0
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Canonical SMILES O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCN(c1ccccn1)C
Isomeric SMILES O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCN(c1ccccn1)C
InChI InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)
1. Chen X, Yang L, Zhai SD. (2012)
Risk of cardiovascular disease and all-cause mortality among diabetic patients prescribed rosiglitazone or pioglitazone: a meta-analysis of retrospective cohort studies.
Chin Med J, 125 (23): 4301-6. [PMID:23217404]
2. Croppi G, Zhou Y, Yang R, Bian Y, Zhao M, Hu Y, Ruan BH, Yu J, Wu F. (2020)
Discovery of an Inhibitor for Bacterial 3-Mercaptopyruvate Sulfurtransferase that Synergistically Controls Bacterial Survival.
Cell Chem Biol, 27 (12): 1483-1499.e9. [PMID:33186540]
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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]
4. Kotarsky K, Nilsson NE, Flodgren E, Owman C, Olde B. (2003)
A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs.
Biochem Biophys Res Commun, 301 (2): 406-10. [PMID:12565875]
5. Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, Kliewer SA. (1997)
Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs.
J Biol Chem, 272 (6): 3406-10. [PMID:9013583]
6. Liu KG, Lambert MH, Ayscue AH, Henke BR, Leesnitzer LM, Oliver WR, Plunket KD, Xu HE, Sternbach DD, Willson TM. (2001)
Synthesis and biological activity of L-tyrosine-based PPARgamma agonists with reduced molecular weight.
Bioorg Med Chem Lett, 11: 3111-3113. [PMID:11720854]
7. Majeed Y, Bahnasi Y, Seymour VA, Wilson LA, Milligan CJ, Agarwal AK, Sukumar P, Naylor J, Beech DJ. (2011)
Rapid and contrasting effects of rosiglitazone on transient receptor potential TRPM3 and TRPC5 channels.
Mol Pharmacol, 79 (6): 1023-30. [PMID:21406603]
8. 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]