MetyraponeAn inhibitor of cytochrome P450-mediated ω/ω-1 hydroxylase activity and CYP11B1

Metyrapone (CAS 54-36-4)

Metyrapone | CAS 54-36-4 is rated 4.0 out of 5 by 3.
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Synonym: 2-Methyl-1,2-di-3-pyridyl-1-propanone
Application: An inhibitor of cytochrome P450-mediated ω/ω-1 hydroxylase activity and CYP11B1
CAS Number: 54-36-4
Purity: ≥96%
Molecular Weight: 226.27
Molecular Formula: C14H14N2O
* Refer to Certificate of Analysis for lot specific data (including water content).
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Metyrapone inhibits the biosynthesis of corticosteroids. Studies report that Metyrapone inhibits the hydroxylase activity of ω/ω-1 from the cytochrome P450-mediated prostaglandin. Has shown to block glucocorticoid synthesis via inhibition of steroid 11-β hydroxylase (CYP11B1). Small concentrations of Metyrapone are reported to rapidly oxidize endogenous NADPH, improve oxidation of cortisol, and inhibit the reduction of cortisone in rat liver studies. Additionally, depletion of luminal NADPH has been observed in the presence of Metyrapone. Inflammatory studies in rats report that Metyrapone regulates the expression of pro-inflammatory cytokines. Metyrapone is an inhibitor of CYP3A4.


References

1. Tanaka, E., et al. 1991. Biochem. Pharmacol. 41: 472-473. PMID: 1994906
2. Asakura, T. and Shichi, H. 1992. Exp. Eye Res. 55: 377-384. PMID: 1426070
3. Park, H., et al. 2005. J. Am. Chem. Soc. 127: 13634-13642. PMID: 16190729
4. Marcolongo, P., et al. 2008. Biochem. Pharmacol. 76: 382-390. PMID: 18599022
5. Hotham, N.J., et al. 2009. J Hum Lact. 25: 451-454. PMID: 19759353
6. Peruzzo, D.C., et al. 2010. Cytokine. [Epub ahead of print]. PMID: 20702106

Physical State :
Solid
Solubility :
Soluble in methanol, dilute mineral acids, water (<2 mg/mL), DMSO (25 mg/mL), and ethanol (25 mg/mL).
Storage :
Store at room temperature
Melting Point :
52-55° C (lit.)
Boiling Point :
~384.4° C at 760 mmHg (Predicted)
Density :
~1.1 g/cm3 (Predicted)
Refractive Index :
n20D 1.57
IC50 :
CYP11B1: IC50 = 7.83 µM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
UC3050000
PubChem CID :
4174
Merck Index :
13: 6181
MDL Number :
MFCD00006397
EC Number :
200-206-2
Beilstein Registry :
163023
SMILES :
CC(C)(C1=CN=CC=C1)C(=O)C2=CN=CC=C2

Download SDS (MSDS)

Certificate of Analysis

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Rated 2 out of 5 by from Comercial desagradable El envío del producto ha sido rápido, pero el trato de la agente comercial que me atendió no me pareció muy adecuado. Una pena!
Date published: 2017-07-04
Rated 5 out of 5 by from Good! The metyraone is regulates the expression of pro-inflammatory cytokines,and metyrapone is an inhibitor of CYP3A4.The effect is very good.
Date published: 2017-01-30
Rated 5 out of 5 by from Liu Liu, et al. (PubMed ID 26031185) treated 1 group of DSS-induced ulcerative colitis mice with metyrapone after subjection to a 30 day exercise regiment. Results were compared to sedentary DSS treated mice and to DSS treated mice that underwent the same exercise regiment. Found that treatment with metyrapone completely abolished the improvement observed in the clinical symptoms associated with ulcerative colitis. -SCBT Publication Review
Date published: 2015-06-16
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