CH223191

CH223191 is a potent and specific aryl hydrocarbon receptor (AhR) antagonist. CH223191 can prevent 2,3,7,8-TCDD-induced toxicity by antagonizing the aryl hydrocarbon receptor. 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) is a widespread environmental pollutant with many toxic effects, including endocrine disruption, reproductive dysfunction, immunotoxicity, liver damage, and cancer. CH223191 potently inhibits TCDD-induced AhR-dependent transcription. In addition, CH-223191 blocked the binding of TCDD to AhR and inhibited TCDD-mediated nuclear translocation and DNA binding of AhR. These inhibitory effects of CH-223191 prevented the expression of cytochrome P450 enzymes, target genes of the AhR. CH-223191, may be a useful agent for the study of AhR-mediated signal transduction and the prevention of TCDD-associated pathology.

Product information

CAS Number: 301326-22-7

Molecular Weight: 333.39

Formula: C19H19N5O

Synonym:

CH223191

CH-223191

CH 223191

Chemical Name: (E)-1-methyl-N-(2-methyl-4-(o-tolyldiazenyl)phenyl)-1H-pyrazole-5-carboxamide

Smiles: CC1C=C(C=CC=1NC(=O)C1=CC=NN1C)/N=N/C1=CC=CC=C1C

InChiKey: LKTNEXPODAWWFM-GHVJWSGMSA-N

InChi: 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+

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO, not in water

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

In Vitro:

CH223191 (0.1-10 μM; pre-treated 1 hour) inhibits TCDD-caused cytochrome P450 1A1 mRNA expression in a in dose-dependent manner. CH223191 (0.1-10 μM; pre-treated 1 hour) causes a concentration-dependent inhibition of TCDD-induced cytochrome P450 enzyme activity.

In Vivo:

CH223191 (10 mg/kg; once a day; 25 days) suppresses cytochrome P450 1A1 expression and the intrahepatocyte fat content in liver, reduces activity of AST and ALT in TCDD-treated mice.

References:

1. Kim SH, Henry EC, Kim DK, Kim YH, Shin KJ, Han MS, Lee TG, Kang JK, Gasiewicz TA, Ryu SH, Suh PG. Novel compound 2-methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazo-phenyl)-amide (CH-223191) prevents 2,3,7,8-TCDD-induced toxicity by antagonizing the aryl hydrocarbon receptor. Mol Pharmacol. 2006 Jun;69(6):1871-8. Epub 2006 Mar 15. PubMed PMID: 16540597.

Products are for research use only. Not for human use.