Chemical Compound Review:
Metopiron 2-methyl-1,2-dipyridin-3-yl- propan-1-one
Synonyms:
Metopirone, metyrapone, Methopyrapone, Methbipyranone, Su 4885, ...
Jahn,
Schick,
Kiefer,
Kellner,
Yassouridis,
Wiedemann,
Kellner,
Schick,
Yassouridis,
Struttmann,
Wiedemann,
Alm,
Lupien,
Wilkinson,
Brière,
Ng Ying Kin,
Meaney,
Nair,
Otte,
Muhtz,
Daneshkhah,
Yassouridis,
Kiefer,
Wiedemann,
Kellner,
Park,
Lee,
Suh,
Jahn,
Kiefer,
Schick,
Yassouridis,
Steiger,
Kellner,
Wiedemann,
- Metyrapone test with adrenocorticotrophic levels. Separating primary from secondary adrenal insufficiency. Dolman, L.I., Nolan, G., Jubiz, W. JAMA (1979)
- The metyrapone and dexamethasone suppression tests for the differential diagnosis of the adrenocorticotropin-dependent Cushing syndrome: a comparison. Avgerinos, P.C., Yanovski, J.A., Oldfield, E.H., Nieman, L.K., Cutler, G.B. Ann. Intern. Med. (1994)
- The Cushing syndrome induced by bronchial carcinoid tumors. Limper, A.H., Carpenter, P.C., Scheithauer, B., Staats, B.A. Ann. Intern. Med. (1992)
- Pheromone anosmia in a scarab beetle induced by in vivo inhibition of a pheromone-degrading enzyme. Maïbèche-Coisne, M., Nikonov, A.A., Ishida, Y., Jacquin-Joly, E., Leal, W.S. Proc. Natl. Acad. Sci. U.S.A. (2004)
- Hemodynamic role of extracellular fluid in hypertension. Tarazi, R.C. Circ. Res. (1976)
- Mineralocorticoid receptor function in posttraumatic stress disorder after pretreatment with metyrapone. Otte, C., Muhtz, C., Daneshkhah, S., Yassouridis, A., Kiefer, F., Wiedemann, K., Kellner, M. Biol. Psychiatry (2006)
- Metyrapone tests in patients with panic disorder. Kellner, M., Schick, M., Yassouridis, A., Struttmann, T., Wiedemann, K., Alm, B. Biol. Psychiatry (2004)
- Declarative memory after stress in humans: differential involvement of the beta-adrenergic and corticosteroid systems. Maheu, F.S., Joober, R., Lupien, S.J. J. Clin. Endocrinol. Metab. (2005)
- Acute modulation of aged human memory by pharmacological manipulation of glucocorticoids. Lupien, S.J., Wilkinson, C.W., Brière, S., Ng Ying Kin, N.M., Meaney, M.J., Nair, N.P. J. Clin. Endocrinol. Metab. (2002)
- Sleep endocrine effects of the 11-beta-hydroxysteroiddehydrogenase inhibitor metyrapone. Jahn, H., Kiefer, F., Schick, M., Yassouridis, A., Steiger, A., Kellner, M., Wiedemann, K. Sleep. (2003)
- Presence of immunoreactive beta-endorphin in normal human plasma: a concomitant release of beta-endorphin with adrenocorticotropin after metyrapone administration. Nakao, K., Nakai, Y., Oki, S., Horii, K., Imura, H. J. Clin. Invest. (1978)
- Metyrapone as additive treatment in major depression: a double-blind and placebo-controlled trial. Jahn, H., Schick, M., Kiefer, F., Kellner, M., Yassouridis, A., Wiedemann, K. Arch. Gen. Psychiatry (2004)
- Augmented pituitary corticotropin response to a threshold dosage of human corticotropin-releasing hormone in depressives pretreated with metyrapone. Lisansky, J., Peake, G.T., Strassman, R.J., Qualls, C., Meikle, A.W., Risch, S.C., Fava, G.A., Zownir-Brazis, M., Hochla, P., Britton, D. Arch. Gen. Psychiatry (1989)
- Cushing's disease in a patient with a 'nonfunctioning' pituitary tumor. Spontaneous development and remission. Gogel, E.L., Salber, P.R., Tyrrell, J.B., Rosenblum, M.L., Findling, J.W. Arch. Intern. Med. (1983)
- Atypical adrenal insufficiency with failure of the pituitary feedback receptor. A case with associated diabetes mellitus and selective IgA deficiency with steatorrhea. Hagen, G.A., Bolman, R.M., Frank, J.P. Am. J. Med. (1975)
- Inhibition of the morning cortisol peak abolishes the expected morning decrease in serum osteocalcin in normal males: evidence of a controlling effect of serum cortisol on the circadian rhythm in serum osteocalcin. Nielsen, H.K., Brixen, K., Kassem, M., Charles, P., Mosekilde, L. J. Clin. Endocrinol. Metab. (1992)
- Studies of ACTH secretion control in 116 cases of Cushing's syndrome. Raux, M.C., Binoux, M., Luton, J.P., Gourmelen, M., Girard, F. J. Clin. Endocrinol. Metab. (1975)
- The effects of agents that bind to cytochrome P-450 on hypoxic pulmonary vasoconstriction. Sylvester, J.T., McGowan, C. Circ. Res. (1978)
- Paracrine glucocorticoid activity produced by mouse thymic epithelial cells. Pazirandeh, A., Xue, Y., Rafter, I., Sjövall, J., Jondal, M., Okret, S. FASEB J. (1999)
- Metabolic activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone as measured by DNA alkylation in vitro and its inhibition by isothiocyanates. Guo, Z., Smith, T.J., Thomas, P.E., Yang, C.S. Cancer Res. (1991)
- Single turnover kinetics of the reaction between oxycytochrome P-450cam and reduced putidaredoxin. Brewer, C.B., Peterson, J.A. J. Biol. Chem. (1988)
- Recovery of Ca2+ pools and growth in Ca2+ pool-depleted cells is mediated by specific epoxyeicosatrienoic acids derived from arachidonic acid. Graber, M.N., Alfonso, A., Gill, D.L. J. Biol. Chem. (1997)
- Cytotoxicity of mitomycin C and adriamycin in freshly isolated rat hepatocytes: the role of cytochrome P450. Goeptar, A.R., Groot, E.J., Scheerens, H., Commandeur, J.N., Vermeulen, N.P. Cancer Res. (1994)
- Inhibition of cortisol production with metyrapone prevents mental stress-induced endothelial dysfunction and baroreflex impairment. Broadley, A.J., Korszun, A., Abdelaal, E., Moskvina, V., Jones, C.J., Nash, G.B., Ray, C., Deanfield, J., Frenneaux, M.P. J. Am. Coll. Cardiol. (2005)
- Pituitary function after removal of pituitary microadenomas in Cushing's disease. Schnall, A.M., Brodkey, J.S., Kaufman, B., Pearson, O.H. J. Clin. Endocrinol. Metab. (1978)
- Metyrapone, an inhibitor of glucocorticoid production, reduces brain injury induced by focal and global ischemia and seizures. Smith-Swintosky, V.L., Pettigrew, L.C., Sapolsky, R.M., Phares, C., Craddock, S.D., Brooke, S.M., Mattson, M.P. J. Cereb. Blood Flow Metab. (1996)
- Formation of cis-14,15-oxido-5,8,11-icosatrienoic acid from phosphatidylinositol in human platelets. Ballou, L.R., Lam, B.K., Wong, P.Y., Cheung, W.Y. Proc. Natl. Acad. Sci. U.S.A. (1987)
- Nature of endothelium-derived relaxing factor: are there two relaxing mediators? Rubanyi, G.M., Vanhoutte, P.M. Circ. Res. (1987)
- 11beta-hydroxysteroid dehydrogenase expression and activity in the human adrenal cortex. Mazzocchi, G., Rossi, G.P., Neri, G., Malendowicz, L.K., Albertin, G., Nussdorfer, G.G. FASEB J. (1998)
- Structural and dynamical basis of broad substrate specificity, catalytic mechanism, and inhibition of cytochrome P450 3A4. Park, H., Lee, S., Suh, J. J. Am. Chem. Soc. (2005)
- Neuroactive steroid concentrations following metyrapone administration in depressed patients and healthy volunteers. Rupprecht, R., Ströhle, A., Hermann, B., di Michele, F., Spalletta, G., Pasini, A., Holsboer, F., Romeo, E. Biol. Psychiatry (1998)
- Baculovirus-mediated expression and characterization of rat CYP2A3 and human CYP2a6: role in metabolic activation of nasal toxicants. Liu, C., Zhuo, X., Gonzalez, F.J., Ding, X. Mol. Pharmacol. (1996)
- Functional maturation of the primate fetal adrenal in vivo: 3. Specific zonal localization and developmental regulation of CYP21A2 (P450c21) and CYP11B1/CYP11B2 (P450c11/aldosterone synthase) lead to integrated concept of zonal and temporal steroid biosynthesis. Coulter, C.L., Jaffe, R.B. Endocrinology (1998)
- Functional maturation of the primate fetal adrenal in vivo: I. Role of insulin-like growth factors (IGFs), IGF-I receptor, and IGF binding proteins in growth regulation. Coulter, C.L., Goldsmith, P.C., Mesiano, S., Voytek, C.C., Martin, M.C., Han, V.K., Jaffe, R.B. Endocrinology (1996)
- Effect of the adrenal 11-beta-hydroxylase inhibitor metyrapone on human hepatic cytochrome P-450 expression: induction of cytochrome P-450 3A4. Harvey, J.L., Paine, A.J., Maurel, P., Wright, M.C. Drug Metab. Dispos. (2000)
- Aminoglutethimide suppresses adrenocorticotropin receptor expression in the NCI-h295 adrenocortical tumor cell line. Fassnacht, M., Beuschlein, F., Vay, S., Mora, P., Allolio, B., Reincke, M. J. Endocrinol. (1998)
- Hormone secretion in alcohol-induced pseudo-Cushing's syndrome. Differential diagnosis with Cushing disease. Lamberts, S.W., Klijn, J.G., de Jong, F.H., Birkenhäger, J.C. JAMA (1979)
- Multifactorial analysis of chronic hypertension induced by electrolyte-active steroids in trained, unanesthetized dogs. Bravo, E.L., Tarazi, R.C., Dustan, H.P. Circ. Res. (1977)
- Electroconvulsive therapy for iatrogenic hypothalamic-hypopituitarism (CRF-ACTH type). Pitts, F.N., Patterson, C.W. The American journal of psychiatry. (1979)