Synthetic Route of C17H19N3O2S. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Role of CYP3A4 in the regulation of the aryl hydrocarbon receptor by omeprazole sulphide. Author is Gerbal-Chaloin, Sabine; Pichard-Garcia, Lydiane; Fabre, Jean-Michel; Sa-Cunha, Antonio; Poellinger, Lorenz; Maurel, Patrick; Daujat-Chavanieu, Martine.
Cross-talk between nuclear receptors involved in the control of drug metabolism is being increasingly recognized as a source of drug side effects. Omeprazole is a well known activator of the aryl hydrocarbon receptor (AhR). We investigated the regulation of AhR by omeprazole-sulfide, a degradation metabolite of omeprazole, using CYP1A mRNA induction, reporter gene assay, receptor DNA binding, ligand binding, nuclear translocation, trypsin digests, and drug metabolism anal. in mouse Hepa-1c1c7, human HepG2 cells and primary human hepatocytes. Omeprazole-sulfide is a pure antagonist of AhR in Hepa-1c1c7 and HepG2 hepatoma cell lines. In Hepa-1c1c7 cells, omeprazole-sulfide is a ligand of AhR, inhibits AhR activation to a DNA-binding form, induces a specific pattern of AhR trypsin digestion and inhibits AhR nuclear translocation and subsequent degradation in response to 2,3,7,8-tetrachlorodibenzo-p-dioxin. However, in highly differentiated primary human hepatocytes treated with rifampicin an agonist of the pregnane X receptor (PXR), omeprazole-sulfide behaves as an agonist of AhR. Inhibition of drug metabolizing enzymes by ketoconazole restores the antagonist effect of omeprazole-sulfide. Metabolic LC/MS anal. reveals that omeprazole-sulfide (AhR antagonist) is efficiently converted to omeprazole (AhR activator) by cytochrome P 450 CYP3A4, a target gene of PXR, in primary human hepatocytes but not in hepatoma cells in which PXR is not expressed. This report provides the first evidence for a cross-talk between PXR/CYP3A4 and AhR. In addition, it clearly shows that conclusions drawn from experiments carried out in cell lines may lead to erroneous in vivo predictions in man.
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