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)
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Summary of Clinical Use Click here for help
An anti-diabetic drug. EMA approvals for this drug have been withdrawn or suspended and use is restricted in the US, as a consequence of increased risk of cardiovascular events (increased risks of heart attacks and death) in type 2 diabetic patients [1].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Highly selective agonist at peroxisome proliferator activated receptors in tissues targeted by insulin such as adipose tissue, skeletal muscle and liver. Activation of these receptors improves control of glucose production, transport and utilisation through regulation of the transcription of insulin-responsive genes. This has the effect enhancing tissue sensitivity to insulin.
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