Inolitazone dihydrochloride - ≥98% , Peroxisome proliferator-activated receptor gamma agonist, CAS No.223132-38-5, Peroxisome proliferator-activated receptor gamma agonist

CAS: 223132-38-5 Cat. No.: I650003 Peso molecular: 575.51 PubChem CID: 16719220

GRADE & PURITY ≥98%

Synonyms

5-[(4-{[6-(4-Amino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-yl]methoxy}phenyl)methyl]-4-hydroxy-1,3-thiazol-2(5H)-one--hydrogen chloride (1/2) | Efatutazone dihydrochloride; CS-7017 dihydrochloride; RS5444 dihydrochloride | 2,4-Thiazolidinedione, 5

Storage

Store at 2-8°C,Desiccated

Shipped In

Wet ice

Descripción general

Inolitazone dihydrochloride (Efatutazone dihydrochloride) is a novel high-affinity PPARγ agonist that is dependent upon PPARγ for its biological activity with IC 50 of 0.8 nM for growth inhibition.

In Vitro

Inolitazone dihydrochloride (Efatutazone dihydrochloride) upregulates the cell cycle kinase inhibitor, p21 WAF1/CIP1 . Silencing p21 WAF1/CIP1 rendered cells insensitive to Inolitazone. A 10 nM dose of Inolitazone activates PPARγ:RXRα-dependent transcription as demonstrated in a transient transfection assay utilizing a PPRE response element fused to a luciferase reporter gene (PPRE3-tk-luc). DRO cells are treated in culture with Inolitazone, Rosiglitazone, or Troglitazone at the indicated concentrations. DRO cells are transiently transfected with PPRE3-tk-luc to examine effective concentrations at which EC 50 occurs. The EC 50 s are 1 nM (Inolitazone), 65 nM (Rosiglitazone) and 631 nM (Troglitazone). Similarly, the calculated inhibitory concentration at IC 50 is 0.8 nM for Inolitazone, 75 nM for Rosiglitazone, and 1412 nM for Troglitazone. Inolitazone specifically activates PPARγ, but not PPARα or PPARδ. Exposure of 10 nM Inolitazone following transient transfection with the appropriate PPAR isoform (γ, α, or δ) and PPAR response element linked to a luciferase reporter in RIE rat small intestinal cell line, which does not express PPARs, yields increased luciferase activity only in the presence of PPARγ and PPRE3-tk-luc. DRO cells are growth inhibited by 10 nM Inolitazone (RS5444) through a PPARγ-dependent mechanism. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Inolitazone dihydrochloride (Efatutazone dihydrochloride) plus Paclitaxel demonstrate additive antiproliferative activity in cell culture and minimal ATC tumor growth. When Inolitazone is administered in the diet to athymic nude mice prior to DRO tumor cell implantation, tumor growth is inhibited in a dose responsive fashion. At the highest dose, 0.025% Inolitazone inhibits growth on day 32 by 94.4% as compared to that of control. In this treatment group, five of 10 animals do not develop demonstrable tumors. In the 0.0025% treatment group, tumor growth is inhibited by 62.3% compared to that of control on day 32 while the 0.00025% dose demonstrated no growth inhibitory activity as compared to control. Tumors is nest allowed to establish in the mouse and began 0.025% Inolitazone treatment of mice 1 week after DRO or ARO tumor cell implantation. Inolitazone treated animals demonstrate tumor growth inhibition of 68.9% in DRO tumors and 48.3% in ARO tumors as compared to that of their respective controls on day 35 . MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:PPARγ

Specifications

Sinónimos

5-[(4-{[6-(4-Amino-3, 5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-yl]methoxy}phenyl)methyl]-4-hydroxy-1, 3-thiazol-2(5H)-one--hydrogen chloride (1/2) | Efatutazone dihydrochloride; CS-7017 dihydrochloride; RS5444 dihydrochloride | 2, 4-Thiazolidinedione, 5

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

Inolitazone dihydrochloride (Efatutazone dihydrochloride) is a novel high-affinity PPARγ agonist that is dependent upon PPARγ for its biological activity with IC 50 of 0.8 nM for growth inhibition.

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C, Desiccated

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

AGONIST

Mecanismo de acción

Peroxisome proliferator-activated receptor gamma agonist

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: CC1=CC(=CC(=C1N)C)OC2=CC3=C(C=C2)N=C(N3C)COC4=CC=C(C=C4)CC5C(=O)NC(=O)S5.Cl.Cl
• IUPAC Name: 5-[[4-[[6-(4-amino-3,5-dimethylphenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;dihydrochloride
• InChIKey: WFIOHOJEIMQCEG-UHFFFAOYSA-N
• INCHI: 1S/C27H26N4O4S.2ClH/c1-15-10-20(11-16(2)25(15)28)35-19-8-9-21-22(13-19)31(3)24(29-21)14-34-18-6-4-17(5-7-18)12-23-26(32)30-27(33)36-23;;/h4-11,13,23H,12,14,28H2,1-3H3,(H,30,32,33);2*1H
• Isómeros SMILES: CC1=CC(=CC(=C1N)C)OC2=CC3=C(C=C2)N=C(N3C)COC4=CC=C(C=C4)CC5C(=O)NC(=O)S5.Cl.Cl
• CAS alternativo: 223132-38-5
• PubChem CID: 16719220
• Términos de entrada MeSH: CS 7017;CS-7017;CS7017;efatutazone;efatutazone hydrochloride;RS 5444;RS-5444;RS5444
• Peso molecular: 575.51

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Clase Organooxygen compounds
      • Subclass Ethers

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Clase: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Diarylethers
• Alternative Parents: Benzimidazoles Aniline and substituted anilines m-Xylenes Phenol ethers Phenoxy compounds Alkyl aryl ethers Thiazolidinediones N-substituted imidazoles Heteroaromatic compounds Dicarboximides Amino acids and derivatives Thiocarbamic acid derivatives Azacyclic compounds Organic oxides Hydrochlorides Hydrocarbon derivatives Carbonyl compounds Primary amines
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Diaryl ether - Benzimidazole - Phenoxy compound - M-xylene - Xylene - Phenol ether - Aniline or substituted anilines - Alkyl aryl ether - Thiazolidinedione - N-substituted imidazole - Monocyclic benzene moiety - Benzenoid - Dicarboximide - Imidazole - Azole - Heteroaromatic compound - Thiazolidine - Amino acid or derivatives - Thiocarbamic acid derivative - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Organic nitrogen compound - Organonitrogen compound - Carbonyl group - Primary amine - Hydrochloride - Hydrocarbon derivative - Organic oxide - Amine - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Solubilidad: DMSO : 25 mg/mL (43.44 mM; Need ultrasonic) H2O : <0.1 mg/mL (insoluble)
• Peso molecular: 575.500 g/mol
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 574.121 Da
• Monoisotopic Mass: 574.121 Da
• Topological Polar Surface Area: 134.000 Ų
• Heavy Atom Count: 38
• Formal Charge: 0
• Complexity: 782.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 3

XLogP3