Molecular structure of Metyrapone, CAS Number: 54-36-4
Metyrapone (CAS 54-36-4)
See product citations (4)
Alternate Names:
2-Methyl-1,2-di-3-pyridyl-1-propanone
Application:
Metyrapone is 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
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Metyrapone inhibits the biosynthesis of corticosteroids. Studies report that Metyrapone inhibits the hydroxylase activity of omega/omega-1 from the cytochrome P450-mediated prostaglandin. Has shown to block glucocorticoid synthesis via inhibition of steroid 11-beta 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.
Metyrapone (CAS 54-36-4) References
- Cytochrome P450-mediated prostaglandin omega/omega-1 hydroxylase activities in porcine ciliary body epithelial cells. | Asakura, T. and Shichi, H. 1992. Exp Eye Res. 55: 377-84. PMID: 1426070
- Structural and dynamical basis of broad substrate specificity, catalytic mechanism, and inhibition of cytochrome P450 3A4. | Park, H., et al. 2005. J Am Chem Soc. 127: 13634-42. PMID: 16190729
- Carbonyl reduction of metyrapone in human liver. | Maser, E., et al. 1991. Biochem Pharmacol. 42 Suppl: S93-8. PMID: 1722672
- Metyrapone prevents cortisone-induced preadipocyte differentiation by depleting luminal NADPH of the endoplasmic reticulum. | Marcolongo, P., et al. 2008. Biochem Pharmacol. 76: 382-90. PMID: 18599022
- Transfer of metyrapone and its metabolite, rac-metyrapol, into breast milk. | Hotham, NJ., et al. 2009. J Hum Lact. 25: 451-4. PMID: 19759353
- Characterization of liver microsomal cytochrome P450 from rats treated with muscone (3-methylcyclopentadecanone). | Tanaka, E., et al. 1991. Biochem Pharmacol. 41: 472-3. PMID: 1994906
- Evidence that metyrapone in the presence of inflammation modulates cytokine mRNA expression. | Peruzzo, DC., et al. 2010. Cytokine. 52: 184-9. PMID: 20702106
- Single administration of metyrapone modifies sleep-wake patterns in the rat. | Drouet, JB., et al. 2011. Eur J Pharmacol. 652: 60-4. PMID: 21114995
- Effect of metyrapone on the fluoxetine-induced change in extracellular dopamine, serotonin and their metabolites in the rat frontal cortex. | Rogóż, Z. and Gołembiowska, K. 2010. Pharmacol Rep. 62: 1015-22. PMID: 21273658
- Effects of the combination of metyrapone and oxazepam on intravenous nicotine self-administration in rats. | Goeders, NE., et al. 2012. Psychopharmacology (Berl). 223: 17-25. PMID: 22418732
- Alteration of the inhibitory effect of metyrapone by reduction to metyrapol during the metabolism of methacetin in vivo in mice. | Maser, E. and Legrum, W. 1985. Naunyn Schmiedebergs Arch Pharmacol. 331: 283-9. PMID: 3937061
- Metyrapone is a competitive inhibitor of 11beta-hydroxysteroid dehydrogenase type 1 reductase. | Sampath-Kumar, R., et al. 1997. J Steroid Biochem Mol Biol. 62: 195-9. PMID: 9393954
- Effects of metyrapone on hepatic cortisone-cortisol conversion in the rat. | Thomson, LM., et al. 1998. Endocr Res. 24: 607-11. PMID: 9888546
Inhibitor of:
11β-HSD2, 3β-HSD2, 3β-HSD3, 3β-HSD4, 3β-HSD5, Aldosterone, c-Erb-A α-2, c-Erb-A β-2, CYP11A1, CYP11B, CYP11B1, Cyp21a1, CYP21A2, CYP2A4, CYP3A4, CYPOR, EG434676, EG545948, Fdx1, GH, GLCCI1, Gonadotropin α, MC2-R, MRAP, Olfr564, Olfr64, StAR, and StARD5.Activator of:
CYP11B2, Cyp3a59, and GMEB-1.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Metyrapone, 200 mg | sc-200597 | 200 mg | $25.00 | |||
Metyrapone, 500 mg | sc-200597A | 500 mg | $56.00 | |||
Metyrapone, 1 g | sc-200597B | 1 g | $86.00 |