rosiglitazone   

GtoPdb Ligand ID: 1056

Synonyms: Avandia® | rosiglizole
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
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
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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1999), EMA (2000))
Withdrawn drug? Yes
IUPAC Name
5-[[4-[2-(methyl-pyridin-2-ylamino)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
International Nonproprietary Names
INN number INN
7662 rosiglitazone
Synonyms
Avandia® | rosiglizole
Database Links
BindingDB Ligand 28681
CAS Registry No. 122320-73-4 (source: ChEBI)
ChEBI CHEBI:50122
ChEMBL Ligand CHEMBL121
DrugBank Ligand DB00412
DrugCentral Ligand 2405
GtoPdb PubChem SID 135650927
NURSA Ligand 10.1621/M7WK877IB8
PubChem CID 77999
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Search UniChem for chemical match using the InChIKey YASAKCUCGLMORW-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone YASAKCUCGLMORW
SynPHARM 79481 (in complex with Peroxisome proliferator-activated receptor-γ)
6357 (in complex with Peroxisome proliferator-activated receptor-γ)
Wikipedia Rosiglitazone

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Rosiglitazone
Cat. No. 5325