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Merck

R2408

Rosiglitazone

≥98% (HPLC), powder, PPARγ agonist

Synonym(s):

Rosiglitazone, 5-[[4-[2-(Methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione

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About This Item

Linear Formula:
C18H19N3O3S
CAS Number:
122320-73-4
Molecular Weight:
357.43
UNSPSC Code:
12352200
PubChem Substance ID:
329824017
NACRES:
NA.77
MDL number:
MFCD00871760

Product Name

Rosiglitazone, ≥98% (HPLC)

SMILES string

CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c3ccccn3

InChI key

YASAKCUCGLMORW-UHFFFAOYSA-N

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)

assay

≥98% (HPLC)

form

powder

solubility

DMSO: ≥10 mg/mL

originator

GlaxoSmithKline

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... PPARG(5468)

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Biochem/physiol Actions

Rosiglitazone is a potent agonist for PPARγ with an EC50 of 43 nM for the human receptor. It is antidiabetic, working as an insulin sensitizer by binding to the PPARγ receptors in fat cells and making the cells more responsive to insulin.
Potent agonist for PPARγ with an EC50 of 43 nM for the human receptor.

Application

Rosiglitazone has been used:
  • as a medium constituent for adipocyte differentiation
  • in the cell proliferation assay in human colonic carcinoma cell lines
  • for Bcl-2-like protein 13 (Bcl2l13) expression in adipocytes
  • as a peroxisome proliferator-activated receptor gamma (PPARγ) ligand

Features and Benefits

This compound is a featured product for ADME Tox and Gene Regulation research. Discover more featured ADME Tox and Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the AMPKs and Nuclear Receptors (PPARs) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

General description

Rosiglitazone is a member of the thiazolidinedione family. It effectively lowers glucose levels by enhancing the response of target cells to insulin, without causing increased stimulation and release of insulin by the pancreatic beta cells. Rosiglitazone functions by activating the nuclear peroxisome proliferator-activated (PPAR) receptor gamma, which plays a key role in regulating adipogenesis, glucose metabolism, and genetic networks. It exhibits high potency as a thiazolidinedione, with a binding affinity for PPAR-gamma that is 30-fold higher than pioglitazone. Furthermore, it increases insulin-stimulated IRS-1/2 in skeletal muscle and adipose tissue, leading to the expression of the GLUT4 glucose transporter.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000509023
0000509026
0000509026
0000509023
0000467836

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Siyu Xie et al.
Nutrients, 11(7) (2019-07-22)
Promoting white-to-beige adipocyte transition is a promising approach for obesity treatment. Although Liensinine (Lie), a kind of isoquinoline alkaloid, has been reported to affect white-to-beige adipocyte transition, its effects on inhibiting beige adipocytes recovering to white adipocytes and maintaining the
Rosiglitazone
Rodriguez BSQ and Correa R
StatPearls [Internet] (2023)
CACUL1 reciprocally regulates SIRT1 and LSD1 to repress PPARgamma and inhibit adipogenesis
Jang MJ, et al.
Cell Death & Disease, 8(12), 3201-3201 (2017)
Spermidine/spermine N1-acetyltransferase-mediated polyamine catabolism regulates beige adipocyte biogenesis
Yuan F, et al.
Metabolism, Clinical and Experimental, 85, 298-304 (2018)
Diego Caprioglio et al.
Planta medica, 85(11-12), 981-986 (2019-04-02)
A general protocol for the selective mono-O-methylation of resorcinyl phytocannabinoids was developed. The availability of semisynthetic monomethyl analogues of cannabigerol, cannabidiol, and cannabidivarin (1A: -3A: , respectively) made it possible to quantify these minor phytocannabinoids in about 40 different chemotypes
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