Rosiglitazone

Base Information

• Chemical Name: Rosiglitazone
• CAS No.: 122320-73-4
• Molecular Formula: C18H19N3O3S
• Molecular Weight: 357.433
• Hs Code.: 2934100000
• European Community (EC) Number: 431-390-4,814-748-8
• NSC Number: 758698
• UNII: 05V02F2KDG
• DSSTox Substance ID: DTXSID7037131
• Nikkaji Number: J620.770G
• Wikipedia: Rosiglitazone
• Wikidata: Q424771
• NCI Thesaurus Code: C62076
• Pharos Ligand ID: M55WRV5WU2U6
• Metabolomics Workbench ID: 145153
• ChEMBL ID: CHEMBL121
• Mol file: 122320-73-4.mol

Synonyms:5-((4-(2-methyl-2-(pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione-2-butenedioate;Avandia;BRL 49653;BRL-49653;BRL49653;rosiglitazone;rosiglitazone maleate

Chemical Property of Rosiglitazone

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 1.14E-13mmHg at 25°C
• Melting Point: 153-155 °C
• Boiling Point: 585 °C at 760mmHg
• PKA: 6.34±0.50(Predicted)
• Flash Point: 307.6 °C
• PSA: 96.83000
• Density: 1.315 g/cm³
• LogP: 2.81970
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 357.11471265
• Heavy Atom Count: 25
• Complexity: 469

Purity/Quality:

99% ^*data from raw suppliers

Rosiglitazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Hypoglycemic Agents
• Canonical SMILES: CN(CCOC1=CC=C(C=C1)CC2C(=O)NC(=O)S2)C3=CC=CC=N3
• Recent ClinicalTrials: Anti-PD-1 mAb Plus Metabolic Modulator in Solid Tumor Malignancies
• Recent EU Clinical Trials: Open-label study to evaluate the efficacy and tolerability of orally administered rosiglitazone in patients with progressive bone Fibrodysplasia (FOP)
• General Description: Rosiglitazone is a thiazolidinedione-class PPARγ agonist used to treat type 2 diabetes by improving insulin sensitivity and glucose metabolism. However, unlike the novel dual-functional agent (11e) described in the study, rosiglitazone is associated with adverse effects such as weight gain and adipogenesis due to its selective PPARγ activation, without inhibitory effects on 11β-HSD1. The study highlights the limitations of rosiglitazone and similar PPARγ agonists, emphasizing the potential advantages of dual-targeting agents that combine PPARγ activation with 11β-HSD1 inhibition to achieve better metabolic outcomes while avoiding undesirable side effects.

Technology Process of Rosiglitazone

There total 22 articles about Rosiglitazone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(Z)-5-[4-[2-[N-methyl-N-(pyridin-2-yl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione (160596-25-8) → rosiglitazone (122320-73-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 24h; under 2585.81 Torr;

DOI:10.1002/asia.201700877

Reference yield: 95.0%

Pioglitazone (105355-27-9,111025-46-8) → rosiglitazone (122320-73-4)

Guidance literature:

In ethanol; at 50 - 80 ℃;

Reference yield: 93.7%

5-{4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzylidene}thiazolin-2,4-dione (122320-74-5) → rosiglitazone (122320-73-4)

Guidance literature:

With BuMnCl; In methanol; at 20 ℃; for 0.5h;

upstream raw materials:

(Z)-5-[4-[2-[N-methyl-N-(pyridin-2-yl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione

thiazoline-2,4-dione

2-fluoropyridine

4-hydroxy-benzaldehyde

Downstream raw materials:

5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione β-cyclodextrin complex 1:1

5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione γ-cyclodextrin complex 1:1

(+)-5-(4-[2-(N-methyl-N-(pyridin-2-yl)amino)ethoxy]-benzyl)thiazolidine-2,4-dione hydrochloride

Refernces

Discovery of novel dual functional agent as PPARγ agonist and 11β-HSD1 inhibitor for the treatment of diabetes

10.1016/j.bmc.2009.05.082

The research aims to develop a new class of dual-functional agents that can simultaneously activate PPARγ and inhibit 11β-HSD1, targeting type 2 diabetes. PPARγ is a receptor involved in regulating glucose and lipid metabolism, while 11β-HSD1 is an enzyme that amplifies local glucocorticoid action and is implicated in insulin resistance. The study synthesized a series of α-aryloxy-α-methylhydrocinnamic acids and evaluated their in vitro and in vivo efficacy. Compound 11e emerged as the most potent, showing significant hypoglycemic and hypolipidemic effects in KKAy mice and MSG rats, with a favorable pharmacokinetic profile. Notably, 11e did not promote adipogenesis and even reduced body weight and fat mass in MSG rats, unlike traditional PPARγ agonists such as rosiglitazone. The research concludes that these dual-functional agents represent a promising new approach for treating type 2 diabetes, potentially offering better therapeutic outcomes while mitigating the weight gain side effects associated with existing treatments.