580563

TCPOBOP

The most potent known member of the phenobarbital-like class of cytochrome P450 (CYP)-inducing agents.

• Synonym(s): TCPOBOP, 1,4-Bis[2-(3,5-dichloropyridyloxy)]benzene
• Empirical Formula (Hill Notation): C₁₆H₈Cl₄N₂O₂
• CAS Number: 76150-91-9
• Molecular Weight: 402.06
• MDL number: MFCD00057368
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥95% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: white
• solubility: DMSO: 5 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• InChI: 1S/C16H8Cl4N2O2/c17-9-5-13(19)15(21-7-9)23-11-1-2-12(4-3-11)24-16-14(20)6-10(18)8-22-16/h1-8H
• InChI key: BAFKRPOFIYPKBQ-UHFFFAOYSA-N

Description

General description

A highly potent inducer of phenobarbital-like class of cytochrome P450 (CYP) enzymes. A tumor promoter that induces hepatocyte proliferation, independent of the presence of cytokines or transcription factors. Activates orphan nuclear receptors mCAR (mouse constitutive androstane receptor) and hPXR (human pregane X receptor), but has little or no effect on hCAR and mPXR. Also suppresses the expression of multi-drug resistance genes mdr2 and mdr3 in mouse liver.

The most potent known member of the phenobarbital-like class of cytochrome P450 (CYP)-inducing agents. Acts as a tumor promoter of murine hepatocarcinogenesis; activates orphan nuclear receptors mCAR (mouse Constitutive Androstane Receptor) and hPXR (human Pregnane X Receptor), but has little or no activity on hCAR and mPXR. Also suppresses the multidrug resistance gene expression in the mouse liver.

Biochem/physiol Actions

Cell permeable: no

Primary Target
Cytochrome P450 (CYP)-inducing agents

Product does not compete with ATP.

Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Carcinogenic / Teratogenic (D)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Ledda-Columbano, G.M., et al. 2000. Am. J. Pathol.156, 91.
Moore, L.B., et al. 2000. J. Biol. Chem.275, 15122.
Tzameli, I., et al. 2000. Mol. Cell. Biol.20, 2951.
Forman, B.M., et al. 1998. Nature395, 612.
Honkakoski, P., et al. 1998. Mol. Pharmacol.53, 597.
Russell, A.L., et al. 1994. Int. J. Cancer58, 550.
Smith, G., et al. 1993. Biochem. J.289, 807.
Dargani, T.A., et al. 1990. Carcinogenesis11, 1153.
Poland, A., et al. 1980. Mol. Pharmacol.18, 571.

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable