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).
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: rosiglitazone

rosiglitazone is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
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)
InChI Key YASAKCUCGLMORW-UHFFFAOYSA-N
References
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]
3. 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]
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]