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Merck

182705

CH-223191

The AhR Antagonist, also referenced under CAS 301326-22-7, controls the biological activity of AhR.

Synonym(s):

AhR Antagonist, 2-Methyl-2H-pyrazole-3-carboxylic acid-(2-methyl-4- o-tolyl-azophenyl)-amide, CH-223191, 2-Methyl-2H-pyrazole-3-carboxylic acid-(2-methyl-4-o-tolyl-azophenyl)-amide, CH-223191

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About This Item

Empirical Formula (Hill Notation):
C19H19N5O
CAS Number:
301326-22-7
Molecular Weight:
333.39
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00377884

Key Documents

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Product Name

AhR Antagonist, The AhR Antagonist, also referenced under CAS 301326-22-7, controls the biological activity of AhR.

SMILES string

[n]1(nccc1C(=O)Nc2c(cc(cc2)\N=N\c3c(cccc3)C)C)C

InChI

1S/C19H19N5O/c1-13-6-4-5-7-17(13)23-22-15-8-9-16(14(2)12-15)21-19(25)18-10-11-20-24(18)3/h4-12H,1-3H3,(H,21,25)/b23-22+

InChI key

LKTNEXPODAWWFM-GHVJWSGMSA-N

assay

≥95% (HPLC)

form

(Orange-brown)

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

orange-brown

solubility

DMSO: 10 mg/mL

shipped in

ambient

storage temp.

2-8°C

Quality Level

100

Biochem/physiol Actions

Cell permeable: yes
Primary Target
AhR (aryl hydrocarbon receptor)
Product does not compete with ATP.
Reversible: no
Target IC50: 30 nM in blocking TCDD-induced AhR transcription activity in HepG2 cells in vitro

Disclaimer

Toxicity: Irritant (B)

General description

A cell-permeable pyrazolo-amide compound that potently blocks the binding of TCDD (2,3,7,8-tetrachlorodibenzo-p-dioxin) to AhR (aryl hydrocarbon receptor) in a dose-dependent manner. Shown to Inhibit TCDD-induced AhR transcription activity in HepG2 cells in vitro (IC50 = 30 nM) and prevent TCDD-elicited liver toxicity and wasting syndrome in mice in vivo. Unlike the commonly used AhR antagonist flavone, this inhibitor has no effect on estrogen receptor transcription activity, nor does it exhibit TCDD-like agonist activity even at concentrations as high as 10 µM.

Other Notes

Kim, S.H., et al. 2006. Mol. Pharmacol.69, 1871.

Packaging

Packaged under inert gas

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Global Trade Item Number

SKUGTIN
182705-10MGCN04055977204452

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