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)
• Description: Rosiglitazone is a type of thiazolidinedione antidiabetics. Thiazolidinedione are agonists for peroxisome-proliferator–activated receptor γ (PPAR-γ). PPAR-γ receptors are ligand-activated nuclear transcription factors that modulate gene expression, lowering blood glucose primarily by increasing insulin sensitivity in peripheral tissues. Rosiglitazone is widely used to lower blood glucose levels in patients with type 2 diabetes mellitus. Rosiglitazone functionalizes by makes the cells of the body more sensitive to the naturally produced insulin in body. It shouldn’t be used if the patient is injecting or inhaling insulin. Using rosiglitazone with insulin could increase the risk of heart failure. Patients having heart failure with symptoms or moderate to severe heart failure should not use Rosiglitazone.
• Uses: antidiabetic A potent and selective PPARγ agonist. Rosiglitazone is an insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR- γ).
• Indications: Rosiglitazone is approved for use as monotherapy and in conjunction with metformin, though it is sometimes combined with a sulfonylurea or insulin. It is usually taken once or twice a day with or without food. Rosiglitazone may cause a modest increase in lowdensity lipoprotein and triglyceride concentrations, but it is unclear whether this effect has any clinical significance or persists in the long term.
• Clinical Use: Although rosiglitazone is extensively biotransformed—playing the major role in both transformations, and some involvementof CYP2C9.21,47 The sulfate conjugate M10 is thepredominant circulating metabolite by 4-hour postdose. Theextraordinarily high plasma protein binding of this metabolite(and the N-demethylated sulfate conjugate M4) in humans accountsfor the lengthy residence time of the radioactivity in thebody, despite the relatively short pharmacokinetic half-life(4–4.5 hours) of rosiglitazone itself.

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 DL-tartrate

avandia

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

p-Hydroxy-Rosiglitazone

Refernces

• 1、 Gaonkar, Santosh L.,Shimizu, Hiroki. "Microwave-assisted synthesis of the antihyperglycemic drug rosiglitazone". . p. 3314 - 3317. Retrieved 2010.
• 2、 Zhou, Hui,Zhang, Rui,Mu, Sen,Zhang, Hui,Lu, Xiao-Bing. "Organocatalytic Cyclization of COS and Propargylic Derivatives to Value-Added Heterocyclic Compounds". . p. 5728 - 5732. Retrieved 2019/06/04.