For research use only. Not for therapeutic Use.
Metyrapone（Cat No.:I003995）is a reversible inhibitor of 11β-hydroxylase, an enzyme involved in the final step of cortisol synthesis in the adrenal cortex. By blocking cortisol production, metyrapone is used diagnostically to assess adrenal function and in the treatment of Cushing’s syndrome, where excess cortisol is produced. Metyrapone is also studied for its potential in modulating the hypothalamic-pituitary-adrenal (HPA) axis and has been explored in research related to stress, depression, and PTSD. Its ability to lower cortisol levels makes it a valuable tool in both clinical and research settings.
| Catalog Number | I003995 |
| CAS Number | 54-36-4 |
| Synonyms | 2-methyl-1,2-di(pyridin-3-yl)propan-1-one |
| Molecular Formula | C14H14N2O |
| Purity | ≥95% |
| Target | Hydroxylases |
| Solubility | H2O: ≥ 38 mg/mL |
| Storage | Store at +4C |
| IUPAC Name | 2-methyl-1,2-dipyridin-3-ylpropan-1-one |
| InChI | 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 |
| InChIKey | FJLBFSROUSIWMA-UHFFFAOYSA-N |
| SMILES | CC(C)(C1=CN=CC=C1)C(=O)C2=CN=CC=C2 |
| Reference | </br>1:Metyrapone prevents brain damage induced by status epilepticus in the rat lithium-pilocarpine model. García-García L, Shiha AA, Fernández de la Rosa R, Delgado M, Silván Á, Bascuñana P, Bankstahl JP, Gomez F, Pozo MA.Neuropharmacology. 2017 May 8. pii: S0028-3908(17)30203-4. doi: 10.1016/j.neuropharm.2017.05.007. [Epub ahead of print] PMID: 28495374 </br>2:Prospective evaluation of a week one overnight metyrapone test with subsequent dynamic assessments of hypothalamic-pituitary-adrenal axis function after pituitary surgery. English K, Inder WJ, Weedon Z, Dimeski G, Sorbello J, Russell AW, Duncan EL, Cuneo R.Clin Endocrinol (Oxf). 2017 Mar 22. doi: 10.1111/cen.13334. [Epub ahead of print] PMID: 28329436 </br>3:A successful case of pregnancy in a woman with ACTH-independent Cushing/’s syndrome treated with ketoconazole and metyrapone. Zieleniewski W, Michalak R.Gynecol Endocrinol. 2017 May;33(5):349-352. doi: 10.1080/09513590.2017.1290070. Epub 2017 Feb 26. PMID: 28277127 </br>4:Effects of the combination of metyrapone and oxazepam on cocaine-induced increases in corticosterone in the medial prefrontal cortex and nucleus accumbens. Keller CM, Breaux KN, Goeders NE.Psychoneuroendocrinology. 2017 Mar;77:75-83. doi: 10.1016/j.psyneuen.2016.12.004. Epub 2016 Dec 9. PMID: 28024272 </br>5:Postnatal treatment with metyrapone attenuates the effects of diet-induced obesity in female rats exposed to early-life stress. Murphy MO, Herald JB, Wills CT, Unfried SG, Cohn DM, Loria AS.Am J Physiol Endocrinol Metab. 2017 Feb 1;312(2):E98-E108. doi: 10.1152/ajpendo.00308.2016. Epub 2016 Dec 13. PMID: 27965205 </br>6:Metal-Free meta-Selective Alkyne Oxyarylation with Pyridine N-Oxides: Rapid Assembly of Metyrapone Analogues. Chen X, Ruider SA, Hartmann RW, González L, Maulide N.Angew Chem Int Ed Engl. 2016 Dec 5;55(49):15424-15428. doi: 10.1002/anie.201607988. Epub 2016 Nov 9. PMID: 27862782 </br>7:Dynamics of Adrenocorticotropin after Application of Metyrapone. Noe S, von Werder A, Iakoubov R, Schneider H, Thaler M, Luppa P, Neu B.Exp Clin Endocrinol Diabetes. 2017 Jan;125(1):53-56. doi: 10.1055/s-0042-117832. Epub 2016 Oct 17. PMID: 27750352 </br>8:Oral pharmacokinetics and in-vitro metabolism of metyrapone in male rats. Murata H, Higuchi T, Otagiri M.J Pharm Pharmacol. 2016 Aug;68(8):970-9. doi: 10.1111/jphp.12560. Epub 2016 Jun 5. PMID: 27265478 </br>9:The first description of metyrapone use in severe Cushing Syndrome due to ectopic ACTH secretion in an infant with immature sacrococcygeal teratoma. Case Report. Wojcik M, Kalicka-Kasperczyk A, Luszawska-Kutrzeba T, Balwierz W, Starzyk JB.Neuro Endocrinol Lett. 2015 Dec;36(7):653-5. PMID: 26859587 </br>10:Antidepressant augmentation with metyrapone for treatment-resistant depression (the ADD study): a double-blind, randomised, placebo-controlled trial. McAllister-Williams RH, Anderson IM, Finkelmeyer A, Gallagher P, Grunze HC, Haddad PM, Hughes T, Lloyd AJ, Mamasoula C, McColl E, Pearce S, Siddiqi N, Sinha BN, Steen N, Wainwright J, Winter FH, Ferrier IN, Watson S; ADD Study Team..Lancet Psychiatry. 2016 Feb;3(2):117-27. doi: 10.1016/S2215-0366(15)00436-8. Epub 2015 Dec 23. PMID: 26727041 |
