Metyrapone - CAS 54-36-4
Catalog number:
54-36-4
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C14H14N2O
Molecular Weight:
226.2774
COA:
Inquire
Targets:
Cytochrome P450
Description:
Metyrapone acts as a glucocorticoid synthesis inhibitor, blocks cortisol synthesis by inhibiting steroid 11β-hydroxylase in adrenal cortex (IC50 = 7.8 μM).
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Purity:
≥98%
Appearance:
Pale Beige to Light Beige Solid
Synonyms:
2-methyl-1,2-di-3-pyridyl-1-propanone; 2-methyl-1,2-dipyridin-3-ylpropan-1-one;
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
A glucocorticoid synthesis inhibitor
Quality Standard:
Enterprise Standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Grams-Kilos
Boiling Point:
384.4ºC at 760mmHg
Melting Point:
53-56 ºC
Density:
1.12g/cm3
InChIKey:
FJLBFSROUSIWMA-UHFFFAOYSA-N
InChI:
1S/C14H14N2O/c1-14(2,12-6-4-8-16-10-12)13(17)11-5-3-7-15-9-11/h3-10H,1-2H3
Canonical SMILES:
CC(C)(C1=CN=CC=C1)C(=O)C2=CN=CC=C2
1.Purification, stabilization and characterization of tomato fatty acid hydroperoxide lyase.
Suurmeijer CN1, Pérez-Gilabert M, van Unen DJ, van der Hijden HT, Veldink GA, Vliegenthart JF. Phytochemistry. 2000 Jan;53(2):177-85.
Fatty acid hydroperoxide lyase (HPO-lyase) was purified 300-fold from tomatoes. The enzymatic activity appeared to be very unstable, but addition of Triton X100 and beta-mercaptoethanol to the buffer yielded an active enzyme that could be stored for several months at -80 degrees C. The enzyme was inhibited by desferoxamine mesylate (desferal), 2-methyl-1,2-di-3-pyridyl-1-propanone (metyrapone), nordihydroguaiaretic acid (NDGA), n-propyl gallate and butylated hydroxyanisole, suggesting the involvement of free radicals in the reaction mechanism and the existence of a prosthetic group in the active center. However, no heme group could be demonstrated with the methods commonly used to identify heme groups in proteins. Only 13-hydroperoxides from linoleic acid (13-HPOD) and alpha-linolenic acid (alpha-13-HPOT) were cleaved by the tomato enzyme, with a clear preference for the latter substrate. The pH-optimum was 6.5, and for concentrations lower than 300 microM a typical Michaelis-Menten curve was found with a K(m) of 77 microM.
2.A regulatory role for cortisol in muscle glycogen metabolism in rainbow trout Oncorhynchus mykiss Walbaum.
Milligan CL1. J Exp Biol. 2003 Sep;206(Pt 18):3167-73.
To test the hypothesis that cortisol has a regulatory role in fish muscle glycogenesis post-exercise, rainbow trout were treated 1 h prior to exercise with either saline (control) or metyrapone (2-methyl-1, 2-di-3-pyridyl-1-propanone) to block cortisol synthesis. Following exercise (time 0), half of the metyrapone-treated fish received a single injection of cortisol, to mimic the post-exercise rise usually observed. Muscle glycogen and the relative activities of glycogen phosphorylase a (Phos a) and glycogen synthase I (GSase I), regulatory enzymes for glycogen resynthesis, were monitored 4 h post-exercise. Metyrapone treatment succeeded in blocking the post-exercise rise in plasma cortisol (17+/-2 vs 118+/-13 ng ml(-1) in controls at time 0), and cortisol injection resulted in a larger and more prolonged cortisol increase than in controls (159+/-22 vs 121+/-14 ng ml(-1) in controls at 1 h). Muscle glycogen was completely restored in the metyrapone-treated fish within 2 h after exercise (8.
3.Role of maternal corticosterone in the development and maturation of the aminoacidergic systems of the rat brain.
Leret ML1, Lecumberri M, Garcia-Montojo M, González JC. Int J Dev Neurosci. 2007 Nov;25(7):465-71. Epub 2007 Aug 19.
Previous studies have suggested an important role for maternal glucocorticoids in the development of the aminoacidergic systems of the rat brain. This study examines the effect of metyrapone (2-methyl-1,2-di-3-pyridyl-1-propanone), i.p.-administered to gestating mothers, on the maturation of the aminoacidergic systems of their offsprings' brains. gamma-Aminobutyric acid (GABA) and glutamate concentrations were determined in male and female offspring at postnatal days (PN) 23 and 90 in four brain areas: the hippocampus, hypothalamus, striatum and cortex. The activity of glutamic acid decarboxylase (GAD), the most important enzyme in the synthesis of GABA, was also analysed. The results show that a reduction in maternal corticosterone during gestation leads to a reduced GABAergic content in all brain areas studied at PN23; permanent organizational changes occurred in the cortex, striatum and hypothalamus. Maternal metyrapone treatment also affected the development of the glutamatergic systems, females being more affected than males at both PN23 and PN90 particularly in the hypothalamus and cortex.
4.Endothelium- and cytochrome P-450-dependent relaxation induced by isoproterenol in rat aortic rings.
Satake N1, Shibata M, Shibata S. Eur J Pharmacol. 1997 Jan 14;319(1):37-41.
In rat aortic rings, the mechanism of endothelium-dependent relaxation induced by isoproterenol is examined. Pretreatment with (+/-)-1-[2,3]-(dihydro-7-methyl-1H-inden-4-yl)oxy]-3-[(1-methyleth yl)amino] -2-butanol (ICI-118,551), a beta 2-adrenoceptor antagonist, or atenolol, a beta 1-adrenoceptor antagonist, partly inhibited the relaxing response to isoproterenol. The relaxing response to isoproterenol in the presence of ICI-118,551 or atenolol was markedly inhibited by removal of endothelium. In the aorta pretreated with ICI-118,551 or atenolol, residual relaxing response to isoproterenol was also inhibited by 2-methyl-1,2-di-3-pyridyl-1-propanone (metyrapone), alpha-naphthoflavone or 8-methoxypsoralen, cytochrome P-450 monoxygenase inhibitors, and methylene blue, but not by indomethacin, a cyclooxygenase inhibitor, 2,3,5-trimethyl-6-(12-hydroxy-5,10-dodecadiynyl)-1, 4-benzoquinone (AA861), a 5-lipoxygenase inhibitor, NG-nitro-L-arginine (NOARG), a nitric oxide synthase inhibitor, Zn protoporphyrin IX, a heme oxygenase inhibitor, or yohimbine, a alpha 2-adrenoceptor antagonist.
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CAS 54-36-4 Metyrapone

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