533659 ERRα Inverse Agonist, C29 - Calbiochem

533659
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Overview

Replacement Information

Key Specifications Table

Empirical Formula
C₁₉H₁₁F₃N₂O₄S

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      Glass bottle 10 mg
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      Description
      OverviewA cell-permeable, orally available diaryl ether-based thiazolidinedione compound that acts as a potent, time-dependent, and slowly reversible inhibitor of ERRα activity (IC50 = 40 nM and 600 nM in TR-FRET and two-hybrid luciferase reporter assay). Directly targets the co-activator groove of ERRα ligand binding domain and covalently modifies Cys325 of helix H3. Displays about 70-fold greater selectivity over ERRγ (IC50 = 2.8 µM) and does not affect the activity of several closely related nuclear receptors (IC50 ≥ 6.3 µM for ERα and ERβ and > 8.3 µM against LXRα, LXRβ, RARα in functional assays). Also, does not affect the activity of PPARα, γ, and δ (IC50 >15 µM) and displays trivial interaction with 51-receptors and ion-channels and 50-protein kinases. Displays desirable pharmacokinetic properties with t1/2 = 7.8 h and Cmax = 6.3 mg/ml (10 mg/kg, oral). Improves insulin sensitivity and glucose tolerance and normalizes circulating triglyceride levels in rodent models of obesity and overt diabetes (10 mg/kg, p.o., q.d.).

      Please note that the molecular weight for this compound is batch-specific due to variable water content. Please refer to the vial label or the certificate of analysis for the batch-specific molecular weight. The molecular weight provided represents the baseline molecular weight without water.
      Catalogue Number533659
      Brand Family Calbiochem®
      Synonyms(Z)-4-(4-((2,4-Dioxothiazolidin-5-ylidene)methyl)-2-methoxyphenoxy)-3-(trifluoromethyl)benzonitrile, Estrogen-Related Receptor α Inverse Agonist, NR3B1 Inverse Agonist
      References
      ReferencesChaveroux, C., et al. 2013. Cell Metab. 17, 586.
      Patch, R.J., et al. 2011. J. Med. Chem. 54, 788.
      Product Information
      FormPale yellow solid
      Hill FormulaC₁₉H₁₁F₃N₂O₄S
      Chemical formulaC₁₉H₁₁F₃N₂O₄S
      ReversibleY
      Quality LevelMQ100
      Applications
      Biological Information
      Primary TargetERRα
      Purity≥98% by HPLC
      Physicochemical Information
      Cell permeableY
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      Safety Information
      Product Usage Statements
      Storage and Shipping Information
      Ship Code Ambient Temperature Only
      Toxicity Standard Handling
      Storage +2°C to +8°C
      Protect from Light Protect from light
      Do not freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
      Packaging Information
      Packaged under inert gas Packaged under inert gas
      Transport Information
      Supplemental Information
      Specifications

      Documentation

      ERRα Inverse Agonist, C29 - Calbiochem SDS

      Title

      Safety Data Sheet (SDS) 

      References

      Reference overview
      Chaveroux, C., et al. 2013. Cell Metab. 17, 586.
      Patch, R.J., et al. 2011. J. Med. Chem. 54, 788.
      Data Sheet

      Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

      Revision20-November-2015 JSW
      Synonyms(Z)-4-(4-((2,4-Dioxothiazolidin-5-ylidene)methyl)-2-methoxyphenoxy)-3-(trifluoromethyl)benzonitrile, Estrogen-Related Receptor α Inverse Agonist, NR3B1 Inverse Agonist
      DescriptionA cell-permeable diaryl ether-based thiazolidinedione compound that acts as a highly selective reverse agonist against ERRα-, but not ERRγ-, dependent reporter transcription in HEK293E cells (IC50 = 600 nM vs. >15 µM) by targeting ERRα ligand binding domain (LBD; aa 289-519 of human ERRα) in a covalent and slowly reversible manner, resulting in a low-affinity LBD conformation toward coactivator SRC2 binding (IC50 = 40 nM against 6 nM ERRα LBD & 6 nM hSRC2 equilibrium binding) without affecting ERα/β, PPARα/γ/PPARδ, or RXRα transcription activity in an agonistic (EC50 >15 µM) or antagonistic manner (IC50 >15 µM against respective agonist-induced activity; 10 nM E2/3301, 400 nM GW7647/370698, 350 nM rosiglitazone/557366, 300 nM GW0742, 2.7 nM bexarotene/200499). Additional selectivity profiling reveals much reduced or little inhibitory potency against 50 enzymes (≤30% inhibition at 20 µM) or affinity toward a panel of 51 receptors & ion channels. Reported to be orally available in mouse, monkey, dog, and rat species (F = 147%, 118%, 91%, and 77%, respectively; 10 mg/kg p.o.) with good pharmacokinetic properties and exhibit efficacy in improving insulin sensitivity & glucose tolerance with concomitant reduction in blood triglyceride level and % body fat among Zucker diebetic fatty (ZDF) rats (2 to 10 mg/kg/d p.o.) & high-fat diet-fed mice (10 to 30 mg/kg/d p.o.) in vivo without apparent animal toxicity. Enhanced ERRα ubiquitination and proteasomal degradation is reported in murine Hepa 1-6 hepatoma cells upon mTOR inhibition by Rapamycin (Cat. Nos. 553210, 553211, and 553212). Likewise, Rapamycin-induced non-alcoholic fatty liver (NAFL) is seen greatly exacerbated among ERRα-null and C29-treated wild-type mice (10 mg/kg/d i.p.).
      FormPale yellow solid
      Intert gas (Yes/No) Packaged under inert gas
      Chemical formulaC₁₉H₁₁F₃N₂O₄S
      Purity≥98% by HPLC
      SolubilityDMSO (50 mg/ml)
      Storage +2°C to +8°C
      Protect from light
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
      Toxicity Standard Handling
      ReferencesChaveroux, C., et al. 2013. Cell Metab. 17, 586.
      Patch, R.J., et al. 2011. J. Med. Chem. 54, 788.