| Identification | More | [Name]
Rosiglitazone maleate | [CAS]
155141-29-0 | [Synonyms]
5-((4-[2-(METHYL-2-PYRIDINYLAMINO)-ETHOXY]-PHENYL)-METHYLENE)-2,4-THIAZOLIDINEDIONE
5-{p-[2-(methyl-2-pyridylamino)ethoxy]benzyl}-2,4-thiazolidinedione maleate
ROSIGLITAZONE MALEATE
RosiglitazoneTartrate
Avandi
BRL-49653c
RSIGLITAZONEMALEATE | [EINECS(EC#)]
642-163-6 | [Molecular Formula]
C22H23N3O7S | [MDL Number]
MFCD03427306 | [Molecular Weight]
473.5 | [MOL File]
155141-29-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White To Off-White Solid | [Melting point ]
235-240°C | [storage temp. ]
2-8°C | [solubility ]
Soluble in DMSO (up to 50 mg/ml). | [form ]
White powder | [pka]
6.1; 6.8(at 25℃) | [color ]
White | [Usage]
Insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR-). | [BCS Class]
1 | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months | [InChIKey]
HCDYSWMAMRPMST-NTCAYCPXSA-N | [CAS DataBase Reference]
155141-29-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3 |
| Hazard Information | Back Directory | [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. | [Chemical Properties]
White To Off-White Solid | [Originator]
SmithKline Beecham (US) | [Uses]
Insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR- γ). | [Uses]
Thiazole alkanes antidiabetic drug | [Uses]
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. | [Brand name]
Avandia (GlaxoSmithKline). | [General Description]
A thiazolidinedione compound that acts as an anti-diabetic agent and serves as a potent and selective agonist of peroxisome proliferator-activated receptor-g (PPARg) (Kd ~40 nM) in fat cells. Shown to reduce fatty acid uptake and ameliorate lipid metabolism and insulin resistance in animal models of type II diabetes. Reported to activate both a1- and a2-containing AMPK complexes. Unlike troglitazone, it does not induce the activity of P4503A4. Significantly improves the differentiation of C3H10T1/2 stem cells into adipocytes. Shown to block estrogen synthesis by interfering with androgen binding to aromatase, but without affecting aromatase mRNA or protein expression. | [storage]
Store at -20°C | [References]
1) Cantello et al. (1994), [[omega-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents; J. Med. Chem., 37 3977
2) Lehmann et al. (1995) An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor gamma (PPARgamma); J. Biol. Chem., 270 12953
3) Wilson et al. (1996), The structure-activity relationship between peroxisome proliferator-activated receptor gamma agonism and the antihyperglycemic activity of thiazolidinediones; J. Med. Chem., 39 665
4) Haruya et al. (2012), PPARγ agonists induce a white-to-brown fat conversion through stabilization of PRDM16 protein; Cell Metab., 15 395
5) Ruiz-Ojeda et al. (2016), Cell Models and their Application for Studying Adipogenic Differentiation in Relation to Obesity: A Review; Int. J. Mol. Sci., 17 E1040 |
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