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Submit ReviewMetyrapone is a 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.
Metyrapone is also offered as part of the Tocriscreen 2.0 Max and Tocriscreen FDA-Approved Drugs. Find out more about compound libraries available from Tocris.
M. Wt | 226.27 |
Formula | C14H14N2O |
Storage | Store at +4°C |
Purity | ≥98% (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.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solvent | Max Conc. mg/mL | Max Conc. mM | |
---|---|---|---|
Solubility | |||
water | 2.26 | 10 | |
DMSO | 22.63 | 100 |
The following data is based on the product molecular weight 226.27. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
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 |
References are publications that support the biological activity of the product.
Hays et al (1984) Structure-activity relationship study of the inhibition of adrenal cortical 11β-hydroxylase by new metyr. 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
If you know of a relevant reference for Metyrapone, please let us know.
Keywords: Metyrapone, Metyrapone supplier, steroid, 11-β, 11-beta, hydroxylase, inhibitors, inhibits, Cytochrome, P450, CYP11B1, CYP3A4, omega/ω-1, omega-1, Hydroxylases, 3292, Tocris Bioscience
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? Please let us know.
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