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Merck

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

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About This Item

Empirical Formula (Hill Notation):
C16H8Cl4N2O2
CAS Number:
76150-91-9
Molecular Weight:
402.06
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00057368

Key Documents

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Product Name

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

SMILES string

Clc1c(ncc(c1)Cl)Oc2ccc(cc2)Oc3ncc(cc3Cl)Cl

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

RTECS - UT7145000

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

Quality Level

100

Biochem/physiol Actions

Cell permeable: no
Primary Target
Cytochrome P450 (CYP)-inducing agents
Product does not compete with ATP.
Reversible: no

Disclaimer

Toxicity: Carcinogenic / Teratogenic (D)

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.

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.

Packaging

Packaged under inert gas

Preparation Note

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

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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