Key Documents

CH-223191

Name: CH-223191
Brand: SIGMA

≥98% (HPLC), powder, AhR antagonist

Synonym(s):

1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phen yl-1H-pyrazole-5-carboxamide, 2-Methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazo-phenyl)-amide

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About This Item

Empirical Formula (Hill Notation):

C₁₉H₁₉N₅O

CAS Number:

301326-22-7

Molecular Weight:

333.39

UNSPSC Code:

12352200

PubChem Substance ID:

329775161

NACRES:

NA.77

MDL number:

MFCD00377884

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Pricing and availability is not currently available.

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Product Name

CH-223191,

assay

≥98% (HPLC)

Quality Level

100

form

powder

color

orange-brown

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

Cc1cc(ccc1NC(=O)c2ccnn2C)\N=N\c3ccccc3C

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

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This Item	SML1061	SML0143	SML0248
Sigma-Aldrich C8124 CH-223191	Sigma-Aldrich SML1061 PF-04856264	Sigma-Aldrich SML0143 HC-067047	Sigma-Aldrich SML0248 Zolmitriptan
form powder	form powder	form powder	form powder
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
solubility DMSO: ≥20 mg/mL	solubility DMSO: 10 mg/mL, clear	solubility DMSO: ≥15 mg/mL	solubility DMSO: ≥5 mg/mL
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
color orange-brown	color white to light brown	color white to tan	color white to beige

Application

CH-223191 has been used as aryl hydrocarbon receptor (AHR) antagonist in HepaRG cells, TH17-IL-10+ cells and organoids.

Biochem/physiol Actions

CH-223191 is a potent and specific aryl hydrocarbon receptor (AhR) antagonist.

CH-223191 is a potent and specific aryl hydrocarbon receptor (AhR) antagonist. It inhibited TCDD-mediated nuclear translocation and DNA binding of AhR, and inhibited TCDD-induced luciferase activity with an IC50 of 30nM. Unlike some other AhR antagonists which display agonist activity at high concentrations, CH-223191 did not stimulate AhR-dependent transcription even at 100 micromolar. It is also specific for AhR, displaying no affinity for the estrogen receptor, as some other antagonists do.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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An immunoregulatory and tissue-residency program modulated by c-MAF in human TH 17 cells

Aschenbrenner D, et al.

Nature Immunology, 19(10), 1126-1126 (2018)

Surface-bound bovine serum albumin carrier protein as present in recombinant cytokine preparations amplifies T helper 17 cell polarization.

Lei Dong et al.

Scientific reports, 6, 36598-36598 (2016-11-04)

Understanding of T helper 17 lineage (T

Aryl hydrocarbon receptor-dependent retention of nuclear HuR suppresses cigarette smoke-induced cyclooxygenase-2 expression independent of DNA-binding.

Michela Zago et al.

PloS one, 8(9), e74953-e74953 (2013-10-03)

The aryl hydrocarbon receptor (AhR), a ligand-activated transcription factor that responds to man-made environmental toxicants, has emerged as an endogenous regulator of cyclooxygenase-2 (Cox-2) by a mechanism that is poorly understood. In this study, we first used AhR-deficient (AhR(-/-) )

Disruption of aryl hydrocarbon receptor homeostatic levels during embryonic stem cell differentiation alters expression of homeobox transcription factors that control cardiomyogenesis.

Qin Wang et al.

Environmental health perspectives, 121(11-12), 1334-1343 (2013-09-24)

The aryl hydrocarbon receptor (AHR) is a ligand-activated transcription factor that regulates the expression of xenobiotic detoxification genes and is a critical mediator of gene-environment interactions. Many AHR target genes identified by genome-wide gene expression profiling have morphogenetic functions, suggesting

Down-regulation of the expression of alcohol dehydrogenase 4 and CYP2E1 by the combination of alpha-endosulfan and dioxin in HepaRG human cells

Attignon E, et al.

Toxicology in vitro, 45, 309-317 (2017)

View All Related Papers

Global Trade Item Number

SKU	GTIN
C8124-5MG	04061833521823
C8124-25MG	04061833521816

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