| Identification | Back Directory | [Name]
1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide | [CAS]
301326-22-7 | [Synonyms]
CS-2720
CH 223191
AhR Antagonist
CH223191;CH 223191
AhR Antagonist - CAS 301326-22-7 - Calbiochem
2-methyl-N-[2-methyl-4-[(2-methylphenyl)diazenyl]phenyl]pyrazole-3-c
2-Methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazo-phenyl)-amide
(E)-1-methyl-N-(2-methyl-4-(o-tolyldiazenyl)phenyl)-1H-pyrazole-5-carboxamide
1-Methyl-N-[2-methyl-4-[(2-methylphenyl)azo]phenyl]-1H-pyrazole-5-carboxamide
2-methyl-N-[2-methyl-4-[(2-methylphenyl)diazenyl]phenyl]pyrazole-3-carboxamide
1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide
1H-Pyrazole-5-carboxamide, 1-methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl]-
1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide USP/EP/BP | [Molecular Formula]
C19H19N5O | [MDL Number]
MFCD00377884 | [MOL File]
301326-22-7.mol | [Molecular Weight]
333.387 |
| Chemical Properties | Back Directory | [Melting point ]
>164°C (dec.) | [Boiling point ]
469.4±45.0 °C(Predicted) | [density ]
1.20±0.1 g/cm3(Predicted) | [storage temp. ]
Store at +4°C | [solubility ]
DMSO: ≥20mg/mL | [form ]
powder | [pka]
12.98±0.70(Predicted) | [color ]
orange-brown | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. | [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+ | [InChIKey]
LKTNEXPODAWWFM-GHVJWSGMSA-N | [SMILES]
[n]1(nccc1C(=O)Nc2c(cc(cc2)\N=N\c3c(cccc3)C)C)C |
| Hazard Information | Back Directory | [Description]
CH-221391 (CAS 301326-22-7) is an arylhydrocarbon (AhR) receptor antagonist, IC50=30 nM.1 Blocks endogenous AhR agonist-induced differentiation of Th17 cells.2?? Promotes expansion of human hematopoietic stem cells.3 Mitigates cytokine-mediated inflammatory signaling in human fibroblast-like synoviocytes.4 An important tool for probing the involvement of AhR in the toxicity of various environmental toxins such as TCDD and other dioxins.5 | [Uses]
CH-223191 has been used as aryl hydrocarbon receptor (AHR) antagonist in HepaRG cells, TH17-IL-10+ cells and organoids. | [Definition]
ChEBI: 2-methyl-N-[2-methyl-4-(2-methylphenyl)azophenyl]-3-pyrazolecarboxamide is an aromatic amide. | [Biochem/physiol Actions]
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. | [storage]
Store at -20°C | [References]
1) Kim et al. (2006), 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., 69 1871
2) Veldhoen et al. (2009), Natural agonists for aryl hydrocarbon receptor in culture medium are essential for optimal differentiation of Th17 T cells; J. Exp. Med., 206 43
3) Carlin et al. (2013), T-cell potential of human adult and cord blood hemopoietic stem cells expanded with the use of aryl hydrocarbon receptor antagonists; Cytotherapy, 15 224
4) Lahoti et al. (2013), Aryl hydrocarbon receptor antagonism mitigates cytokine-mediated inflammatory signaling in primary human fibroblast-like synoviocytes; Ann. Rheum. Dis, 72 1708
5) Petroff et al. (2011), The aryl hydrocarbon receptor agonist 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) alters early embryonic development in a rat IVF exposure model; Reprod. Toxicol., 32 286 |
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