Rosiglitazone Maleate

Base Information

• Chemical Name: Rosiglitazone Maleate
• CAS No.: 155141-29-0
• Molecular Formula: C18H19N3O3S^.C4H4O4
• Molecular Weight: 473.507
• Hs Code.: 2933990090
• UNII: KX2339DP44
• ChEMBL ID: CHEMBL843
• DSSTox Substance ID: DTXSID2023569
• NCI Thesaurus Code: C2583
• NSC Number: 717764
• Pharos Ligand ID: M55WRV5WU2U6
• RXCUI: 253198
• Wikidata: Q27888042
• Mol file: 155141-29-0.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 Maleate

Chemical Property:

• Appearance/Colour: white to off-white solid
• Melting Point: 235-240 °C
• Boiling Point: 585 °C at 760 mmHg
• PKA: 6.1; 6.8(at 25℃)
• Flash Point: 307.6 °C
• PSA: 96.83000
• LogP: 3.24950
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in DMSO (up to 50 mg/ml).
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 473.12567125
• Heavy Atom Count: 33
• Complexity: 588

Purity/Quality:

99.9% ^*data from raw suppliers

Rosiglitazone maleate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-36/38
• Safety Statements: 24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(CCOC1=CC=C(C=C1)CC2C(=O)NC(=O)S2)C3=CC=CC=N3.C(=CC(=O)O)C(=O)O
• Isomeric SMILES: CN(CCOC1=CC=C(C=C1)CC2C(=O)NC(=O)S2)C3=CC=CC=N3.C(=C\C(=O)O)\C(=O)O
• Recent ClinicalTrials: Rosiglitazone in Treating Patients With Liposarcoma
• 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 maleate, belongs to a novel class of thiazolidine diones launched for the treatment of non-insulin-dependent diabetes mellitus (NIDDM), a disease characterized by a pancreatic β-cell defect and insulin resistance in the liver and peripheral tissues. The racemic base can be obtained by KnSvenagel condensation between 2, 4-thiazolidinedione and the corresponding 4-substituted benzaldehyde (itself prepared in 2 steps from 2-chloropyridine), followed by reduction of the benzylidene. Rosiglitazone was shown to be a potent agonist of peroxisome proliferator activated receptor-gamma (PPARgamma), a nuclear receptor involved in the differentiation of adipose tissue, without activating liver PPAR-alpha receptors. This activation of PPAR-gamma could mediate the down-regulation of leptin gene expression. In animal models, Rosiglitazone has been shown to normalize glucose metabolism and reduce the exogenous dose of insulin needed to achieve glycemic control. In patients with Type II diabetes, daily doses (4 or 8 mg) of Rosiglitazone significantly improved blood sugar control without affecting cardiac structure or function.
• Uses: Insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR- γ). Thiazole alkanes antidiabetic drug Thiazolidinediones (TZDs) are a group of structurally related peroxisome proliferator-activated receptor γ (PPARγ) agonists with antidiabetic actions in vivo. Rosiglitazone is a prototypical TZD that has served as a reference compound for this class. It is a potent and selective PPARγ ligand that binds to the PPARγ ligand-binding domain with a Kd value of 43 nM. It activates luciferase-based expression constructs PPARγ1 and PPARγ2 with EC50 values of approximately 30 nM and 100 nM, respectively. Rosiglitazone is active in vivo as an antidiabetic agent in the ob/ob mouse model, and has been used as an oral hypoglycemic agent in the treatment of type 2 diabetes in humans for many years.[Cayman Chemical]
• Indications: Rosiglitazone maleate is an antihyperglycemic agent in the thiazolidinedione class. It is indicated for the treatment of patients with type 2 diabetes mellitus.

Technology Process of Rosiglitazone Maleate

There total 2 articles about Rosiglitazone Maleate 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: 96.0%

maleic acid (110-16-7,26099-09-2) + rosiglitazone (122320-73-4) → avandia (155141-29-0)

Guidance literature:

In isopropyl alcohol; for 1h; Heating; Reflux;

Reference yield: 95.0%

→ avandia (155141-29-0)

Guidance literature:

Reference yield:

avandia (155141-29-0) → 2-N-{5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione}-butanedioic acid (956239-35-3)

Guidance literature:

avandia; With water; In water; at 70 ℃; for 120h;

With trifluoroacetic acid; In methanol; water; at 2 - 8 ℃; for 120h; pH=~ 2.8; Product distribution / selectivity;

upstream raw materials:

maleic acid

rosiglitazone

Downstream raw materials:

2-N-{5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione}-butanedioic acid

Refernces

• 1、 -. "PREPARATION OF ROSIGLITAZONE AND ITS SALTS". Page/Page column 9. . Retrieved 2008/06/13.
• 2、 -. "NEW POLYMORPHOUS FORM OF ROSIGLITAZONE MALEATE". Page/Page column 4-5. . Retrieved 2008/06/13.