All Photos(1)
Synonym(s):
3-[4-(2,4-Bis-trifluoromethylbenzyloxy)-3-methoxyphenyl]-2-cyano-N-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)acrylamide
Empirical Formula (Hill Notation):
C23H13F9N4O3S
CAS Number:
Molecular Weight:
596.42
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
Assay
≥98% (HPLC)
form
solid
color
yellow
solubility
DMSO: ≥10 mg/mL
storage temp.
2-8°C
SMILES string
COc1cc(ccc1OCc2ccc(cc2C(F)(F)F)C(F)(F)F)\C=C(/C#N)C(=O)Nc3nnc(s3)C(F)(F)F
InChI
1S/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+
InChI key
HQFNFOOGGLSBBT-AWNIVKPZSA-N
Related Categories
Application
XCT790 has been used:
- as an estrogen-related receptor (ERR)α inverse agonist in C2C12 myotubes
- as an estrogen-related receptor (ERR)α inverse agonist to elucidate decidualization functionality of ERRα in endometrial embryonic stem cells
- as an autophagy inducer in human neuroblastoma SH-SY5Y and HeLa cell lines.
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).
XCT790 is a potent and specific inverse agonist of ERRα. XCT790 is selective; showing no significant antagonist activity on related nuclear receptors, such as ERRγ or ERα at concentrations below 10 μM. XCT790 inhibits the constitutive activity of ERRα in both biochemical and cell-based assays. The IC50 value is 300-500 nM in transient transfection assays using GAL4-ERR LBD or full-length ERR with the mSHP promoter.
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 4
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Sin-Aye Park et al.
British journal of cancer, 123(6), 988-999 (2020-06-24)
Gremlin-1 (GREM1), one of the bone morphogenetic protein antagonists, is involved in organogenesis, tissue differentiation and kidney development. However, the role of GREM1 in cancer progression and its underlying mechanisms remain poorly understood. The role of GREM1 in breast cancer
Banu Eskiocak et al.
Biochemistry, 53(29), 4839-4846 (2014-07-08)
XCT 790 is widely used to inhibit estrogen-related receptor α (ERRα) activity as an inverse agonist. Here, we report that XCT 790 potently activates AMP kinase (AMPK) in a dose-dependent and ERRα-independent manner, with active concentrations more than 25-fold below
Zhenyu Xu et al.
Theranostics, 10(9), 4201-4216 (2020-04-01)
Enhanced intratumoral androgen biosynthesis and persistent androgen receptor (AR) signaling are key factors responsible for the relapse growth of castration-resistant prostate cancer (CRPC). Residual intraprostatic androgens can be produced by de novo synthesis of androgens from cholesterol or conversion from
PengMing Sun et al.
Cancer management and research, 10, 2521-2535 (2018-08-22)
To explore the targeted therapy of estrogen-related receptor α (ERRα) in endometrial cancer (EC) cells and its potential mechanisms. The mRNA and protein expression levels of ERRα and estrogen receptor α (ERα) were detected by qPCR and Western blotting in
J Z Hu et al.
Neuroscience, 290, 570-580 (2015-02-11)
Estrogen receptor-related receptor-α (ERRα) is an orphan member of the nuclear receptor superfamily that interacts with peroxisome proliferator-activated receptor γ coactivator-1α (PGC-1α) to stimulate vascular endothelial growth factor (VEGF) expression and angiogenesis in a hypoxia-inducible factor-1α-independent pathway. Although it is
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