Rosiglitazone maleate
- Iupac Name：(5E)-5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione
- CAS No.: 155141-29-0
- Molecular Weight：473.5
- Modify Date.: 2022-12-08 16:18
1. Names and Identifiers
- 1.1 Name
- Rosiglitazone maleate
- 1.2 Synonyms
5-((4-[2-(METHYL-2-PYRIDINYLAMINO)-ETHOXY]-PHENYL)-METHYLENE)-2,4-THIAZOLIDINEDIONE 5-(4-(2-(Methyl(pyridin-2-yl)aMino)ethoxy)benzyl)thiazolidine-2,4-dione Maleate 5-{p-[2-(methyl-2-pyridylamino)ethoxy]benzyl}-2,4-thiazolidinedione maleate Avandi BRL-49653c RosiglitazoneTartrate RSIGLITAZONEMALEATE
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- 1.3 CAS No.
- 155141-29-0
- 1.4 CID
- 10111070
- 1.5 EINECS(EC#)
- 642-163-6
- 1.6 Molecular Formula
- C22H23N3O7S (isomer)
- 1.7 Inchi
- SUFUKZSWUHZXAV-BTJKTKAUNA-N
- 1.8 InChIkey
- SUFUKZSWUHZXAV-BTJKTKAUNA-N
- 1.9 Canonical Smiles
- OC(=O)\C=C/C(O)=O.CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1
- 1.10 Isomers Smiles
- OC(=O)\C=C/C(O)=O.CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1
2. Properties
- 2.1 Density
- 1.4±0.1 g/cm3 (Predicted)
- 2.1 Melting point
- 235-240°C
- 2.1 Refractive index
- 1.688 (Predicted)
- 2.1 logP
- 2.38 (Predicted)
- 2.1 pKa
- 6.1; 6.8(at 25℃)
- 2.2 StorageTemp
- 2-8°C
3. Safety and Handling
- 3.1 Hazard Codes
- Xi
- 3.1 Risk Statements
- 20/21/22-36/38
- 3.1 Safety Statements
- 24/25-37/39-26
- 3.1 WGK Germany
- 3
4. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Eye irritation, Category 2
Reproductive toxicity, Category 2
Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |    |
| Signal word | Warning |
| Hazard statement(s) | H319 Causes serious eye irritation H361 Suspected of damaging fertility or the unborn child H411 Toxic to aquatic life with long lasting effects |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P273 Avoid release to the environment. |
| Response | P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P308+P313 IF exposed or concerned: Get medical advice/ attention. P391 Collect spillage. |
| Storage | P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
5. Synthesis Route
155141-29-0Total: 1 Synthesis Route
7. Other Information
- 7.0 Target
- Value
- 7.1 PPARγ ()
- 42 nM
- 7.2 体内研究
-
Rosiglitazone (5 mg/kg, p.o.) decreases the serum glucose in diabetic rats. Rosiglitazone also decreases IL-6, TNF-α, and VCAM-1 levels in diabetic group. Rosiglitazone in combination with losartan increases glucose compared to diabetic and Los-treated groups. Rosiglitazone significantly ameliorates endothelial dysfunction indicated by a significantly lower contractile response to PE and Ang II and enhancement of ACh-provoked relaxation in aortas isolated from diabetic rats.
- 7.3 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.
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- 7.4 Chemical Properties
- White To Off-White Solid
- 7.5 Originator
- SmithKline Beecham (US)
- 7.6 Uses
- Insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR- γ).
- 7.7 Uses
- Thiazole alkanes antidiabetic drug
- 7.8 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]
- 7.9 Indications
- Rosiglitazone maleate is an antihyperglycemic agent in the thiazolidinedione class. It is indicated for the treatment of patients with type 2 diabetes mellitus.
- 7.10 Brand name
- Avandia (GlaxoSmithKline).
- 7.11 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.
- 7.12 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
8. Computational chemical data
- Molecular Weight: 473.5g/mol
- Molecular Formula: C22H23N3O7S
- Compound Is Canonicalized: True
- XLogP3-AA: 3.2
- Exact Mass: 355.09906259
- Monoisotopic Mass: 355.09906259
- Complexity: 518
- Rotatable Bond Count: 6
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 6
- Topological Polar Surface Area: 96.8
- Heavy Atom Count: 25
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 1
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADceB7MABAAAAAAAAAAAAAAAAAAWAAAAA8QAAAAAAAAAABwAAAHgQQAAAADATh2gY/tpPIFAioAjN3dACCiClxIjAJ2CA+bNiOJuLEuZuHOCjsxDPY6aeQwAAOIAAAAAAAAABAAAAAAAAAAAAAAAAAAA==
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