Metyrapone

Pricing Availability Delivery Time Qty
Cat.No. 3292 - Metyrapone | C14H14N2O | CAS No. 54-36-4
Description: 11-β hydroxylase inhibitor
Chemical Name: 2-Methyl-1,2-di-3-pyridinyl-1-propanone
Purity: ≥99% (HPLC)
Datasheet
Citations (3)
Literature

Biological Activity

Cytochrome P450 inhibitor. Blocks glucocorticoid synthesis via inhibition of steroid 11-β hydroxylase (CYP11B1) activity (IC50 = 7.83 μM). Also inhibits CYP3A4 and cytochrome P450-mediated ω/ω-1 hydroxylase activity.

Compound Libraries

Metyrapone is also offered as part of the Tocriscreen Plus and Tocriscreen Library of FDA-Approved Compounds. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 226.27
Formula C14H14N2O
Storage Store at +4°C
Purity ≥99% (HPLC)
CAS Number 54-36-4
PubChem ID 4174
InChI Key FJLBFSROUSIWMA-UHFFFAOYSA-N
Smiles O=C(C2=CN=CC=C2)C(C)(C)C1=CC=CN=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 22.63 100
ethanol 22.63 100
water 22.63 100

Preparing Stock Solutions

The following data is based on the product molecular weight 226.27. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 4.42 mL 22.1 mL 44.19 mL
5 mM 0.88 mL 4.42 mL 8.84 mL
10 mM 0.44 mL 2.21 mL 4.42 mL
50 mM 0.09 mL 0.44 mL 0.88 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Hays et al (1984) Structure-activity relationship study of the inhibition of adrenal cortical 11β-hydroxylase by new metyrapone analogues. J.Med.Chem. 27 15 PMID: 6606707

Asakura and Shichi (1992) Cytochrome P450-mediated prostaglandin omega/omega-1 hydroxylase activities in porcine ciliary body epithelial cells. Exp.Eye Res. 55 377 PMID: 1426070

Park et al (2005) Structural and dynamic basis of broad substrate specificity, catalytic mechanism and inhibition of cytochrome P450 3A4. J.Am.Chem.Soc. 127 13634 PMID: 16190729


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Keywords: steroid 11-β 11-beta hydroxylase inhibitors inhibits Cytochrome P450 CYP11B1 CYP3A4 omega/ω-1 omega-1 Hydroxylases

3 Citations for Metyrapone

Citations are publications that use Tocris products. Selected citations for Metyrapone include:

Taves et al (2016) Lymphoid organs of neonatal and adult mice preferentially produce active glucocorticoids from metabolites, not precursors. Brain Behav.Immun. 57 271 PMID: 27165988

Rincón-Cortés et al (2015) Enduring good memories of infant trauma: rescue of adult neurobehavioral deficits via amygdala serotonin and corticosterone interaction. Brain Res 112 881 PMID: 25561533

Liu et al (2014) Chronic stress impairs GABAergic control of amygdala through suppressing the tonic GABAA receptor currents. Mol Brain 7 32 PMID: 24758222


Do you know of a great paper that uses Metyrapone from Tocris? If so please let us know.

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Literature in this Area

New Product Guide

New Product Guide (Spring/Summer 2017)

Our new product guide highlights over 130 new products added to the Tocris Bioscience range during the first half of 2017.

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  • Fluorescent Imaging
  • Signal Transduction
  • Stem Cells

Pathways for Metyrapone

Protocols

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