315224-26-1

Basic information

• Product Name: INT-131
• Synonyms: INT-131;N-(3,5-DICHLORO-4-QUINOLIN-3-YLOXYPHENYL)-2,4-DIHYDROXYBENZENESULFONAMIDE;2,4-dichloro-N-(3,5-dichloro-4-(quinolin-3-yloxy)phenyl)benzenesulfonamide
• CAS NO: 315224-26-1
• Molecular Formula: C₂₁H₁₂Cl₄N₂O₃S
• Molecular Weight: 514.20858
• EINECS: -0
• Mol File: 315224-26-1.mol

Chemical Properties

• Boiling Point: 611.8±65.0 °C(Predicted)
• Appearance: /
• Density: 1.585±0.06 g/cm3(Predicted)
• PKA: 5.30±0.10(Predicted)
• CAS DataBase Reference: INT-131(CAS DataBase Reference)
• NIST Chemistry Reference: INT-131(315224-26-1)
• EPA Substance Registry System: INT-131(315224-26-1)

Safety Data

• Hazardous Substances Data: 315224-26-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
INT-131 is used as a potential therapeutic agent for type 2 diabetes for its ability to improve insulin sensitivity and lower blood sugar levels. However, due to safety concerns, including an increased risk of heart failure observed in clinical trials, further development of INT-131 as a diabetes treatment has been discontinued.

Upstream product

• 580-18-7 3-hydroxyquinoline 
• 20098-48-0 3,4,5-trichloronitrobenzen 
• 315228-23-0 3-(2,6-dichloro-4-nitrophenoxy)quinoline 
• 315228-24-1 3,5-dichloro-4-(quinolin-3-yloxy)aniline 
• 16271-33-3 2,4-Dichlorobenzenesulfonyl chloride 

Downstream Products

• 1185842-41-4 C₇H₈O₃S*C₂₁H₁₂Cl₄N₂O₃S 
• 1220390-12-4 BrH*C₂₁H₁₂Cl₄N₂O₃S 
• 849738-78-9 2,4-dichloro-N-[3,5-dichloro-4-(quinolin-3-yloxy)-phenyl]-benzenesulfonamide benzenesulfonate salt 

Relevant articles and documents

Structure-Activity Relationship of 2,4-Dichloro-N-(3,5-dichloro-4-(quinolin-3-yloxy)phenyl)benzenesulfonamide (INT131) Analogs for PPARγ-Targeted Antidiabetics

Peroxisome proliferator-activated receptor γ (PPARγ) is a nuclear receptor central to fatty acid and glucose homeostasis. PPARγ is the molecular target for type 2 diabetes mellitus (T2DM) therapeutics TZDs (thiazolidinediones), full agonists of PPARγ with

Discovery of INT131: A selective PPARγ modulator that enhances insulin sensitivity

PPARγ is a member of the nuclear hormone receptor family and plays a key role in the regulation of glucose homeostasis. This Letter describes the discovery of a novel chemical class of diarylsulfonamide partial agonists that act as selective PPARγ modulators (SPPARγMs) and display a unique pharmacological profile compared to the thiazolidinedione (TZD) class of PPARγ full agonists. Herein we report the initial discovery of partial agonist 4 and the structure-activity relationship studies that led to the selection of clinical compound INT131 (3), a potent PPARγ partial agonist that displays robust glucose-lowering activity in rodent models of diabetes while exhibiting a reduced side-effects profile compared to marketed TZDs.

SALTS AND POLYMORPHS OF A POTENT ANTIDIABETIC COMPOUND

Salts and polymorphs of a compound useful in the treatment of inflammatory and metabolic conditions and diseases are provided herein. In particular, the invention provides salts and polymorphs of a compound which modulates the expression and/or function of a peroxisome proliferator-activated receptor. The salts and polymorphs are useful for the treatment or prevention of conditions and disorders associated with energy homeostasis such as type II diabetes, lipid metabolism, adipocyte differentiation and inflammation.

Therapeutic modulation of PPARgamma activity

Modulators of PPARγ activity are used in methods of treating and/or preventing conditions such as osteoporosis, Alzheimer's disease, psoriasis and acne, and cancer.