Rosiglitazone is a potent hypoglycemic agent and a potent thiazolidinedione insulin sensitizer with IC50 of 12,4 and 9 nM in rat, 3T3-L1 and human adipocytes, respectively. Rosiglitazone is a ligand of PPAR-gamma and has no binding force for PPAR-alpha. Rosiglitazone regulates TRP channels and induces autophagy. Rosiglitazone prevents iron death.

 

Brand: BCM

 

Target: Ferroptosis: TRP/TRPV Channel; PPAR; Autophagy

 

Signaling Pathways: Apoptosis; Autophagy; DNA Damage/DNA Repair; Membrane transporter/Ion channel; Metabolism

 

In Vitro: Rosiglitazone reduces the rate of bone formation while increasing the amount of fat in the bone marrow. Rosiglitazone decreased the expression of osteoblast-specific genes Runx2/Cbfa1,DLX5, and α1 (I) collagen, while increased the expression of adipocyte specific fatty acid binding protein AP2. Rosiglitazone causes significant bone loss, including reduced bone mass, trabecular width, and trabecular number, and increased trabecular spacing. Rosiglitazone increased transcription of genes encoding mitochondrial proteins in white adipocytes in ob/ob mice, accompanied by changes in mitochondrial number and mitochondrial structure.

 

Melting Point: 153-155°C

 

Boiling Point: 585.0±35.0 °C(Predicted)

 

pKa: 6.34±0.50(Predicted)

 

Solubility: Soluble in DMSO. Insoluble in Water; Insoluble in Ethanol. 

 

GHS: GHS07, GHS08, GHS09

 

Isomeric SMILES: CN(CCOC1=CC=C(C=C1)CC2C(=O)NC(=O)S2)C3=CC=CC=N3  

 

InChIKey: YASAKCUCGLMORW-UHFFFAOYSA-N  

 

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) 

 

Attribute
[Chem Name]	5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
[Synonym]	Rosiglitazone; BRL 49653
[CAS No.]	122320-73-4
[EINECS]	924-121-1
[MDL No.]	MFCD00871760
[Formula]	C18H19N3O3S
[Molecular]	357.43
[Form]	White to Off-White Powder
[Storage]	Inert atmosphere, 2-8°C

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