725247-18-7

Basic information

• Product Name: XCT 790
• Synonyms: 3-[4-(2,4-bis-trifluoromethylbenzyloxy)-3-methoxyphenyl]-2-cyano-n-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)acrylamide;3-[4-[[2,4-Bis(trifluoromethyl)benzyl]oxy]-3-methoxyphenyl]-2-cyano-N-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)acrylamide XCT 790;XCT 790 3-[4-[[2,4-Bis(trifluoromethyl)benzyl]oxy]-3-methoxyphenyl]-2-cyano-N-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)acrylamide;(E)-3-[4-[[2,4-bis(trifluoromethyl)phenyl]methoxy]-3-methoxyphenyl]-2-cyano-N-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]prop-2-enamide
• CAS NO: 725247-18-7
• Molecular Formula: C23H13F9N4O3S
• Molecular Weight: 596.4249
• Mol File: 725247-18-7.mol
• Article Data: 0

Chemical Properties

• Appearance: yellow/
• Density: 1.544 g/cm³
• Refractive Index: 1.55
• Storage Temp.: Store at +4°C
• Solubility: DMSO: ≥10mg/mL
• CAS DataBase Reference: XCT 790(CAS DataBase Reference)
• NIST Chemistry Reference: XCT 790(725247-18-7)
• EPA Substance Registry System: XCT 790(725247-18-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 725247-18-7(Hazardous Substances Data)

Usage

Description

XCT 790 is an inverse agonist of estrogen-related receptor α (ERRα) with an IC50 of approximately 300-500 nM. It effectively inhibits ERRα constitutive activity by 90-100% and does not exhibit significant activity on related nuclear receptors at a concentration of 10 μM. XCT 790 interacts with the ligand-binding domain of ERRα, blocking ERRα/PGC-1α-dependent signaling and suppressing the expression of monoamine oxidases A and B. Additionally, it promotes proteasomal degradation of ERRα and enhances the degradation of the estrogen receptor ERα by fulvestrant.

Uses

Used in Pharmaceutical Industry:
XCT 790 is used as a therapeutic agent for targeting ERRα, which plays a role in various diseases and conditions. Its potent inverse agonistic activity against ERRα makes it a promising candidate for the development of drugs aimed at treating ERRα-related disorders.
Used in Research Applications:
XCT 790 is used as a research tool for studying the role of ERRα in cellular processes and disease mechanisms. Its ability to inhibit ERRα activity and induce its degradation allows researchers to investigate the functional consequences of ERRα modulation in cellular models and understand the underlying molecular pathways.
Used in Drug Development:
XCT 790 is used as a lead compound in the development of new drugs targeting ERRα. Its high potency and selectivity make it an attractive starting point for designing and optimizing more effective and safer ERRα inverse agonists for therapeutic use.

Biochem/physiol Actions

XCT 790 is a 5′adenosine monophosphate-activated protein kinase (AMPK) activator. It also acts as a proton ionophore and an uncoupler of oxidative phosphorylation in mitochondria. XCT790 impairs vascular endothelial growth factor (VEGF) and angiopoietin 2 (Ang-2) expression and exhibits suppression of endometrial tumor via estrogen-related receptor (ERRα) inhibition. XCT790 mediates cell cycle arrest and favors apoptosis in triple-negative breast cancer (TNBC).

references

[1] lu x, peng l, lv m, ding k. recent advance in the design of small molecular modulators of estrogen-related receptors. curr pharm des. 2012;18(23):3421-31.[2] wu f, wang j, wang y, kwok tt, kong sk, wong c. estrogen-related receptor alpha (erralpha) inverse agonist xct-790 induces cell death in chemotherapeutic resistant cancer cells. chem biol interact. 2009 oct 7;181(2):236-42.

InChI:InChI=1/C23H13F9N4O3S/c1-38-17-7-11(6-13(9-33)18(37)34-20-36-35-19(40-20)23(30,31)32)2-5-16(17)39-10-12-3-4-14(21(24,25)26)8-15(12)22(27,28)29/h2-8H,10H2,1H3,(H,34,36,37)/b13-6+