Flumecinol, a novel inducer of testosterone 16a-hydroxylation in male rats

References

• Bendzko P., Vezekenyi L., Friedrich J., Schwarze W., Ruckpaul K. Effect of flumecinol on the induction of cytochrome P-450 in rats and rabbits,. Cytochrome P-450, Biochemistry, Biophysics and Induction, L. Vezekenyi, K. Magyar. Akademiai Kiado and Amsterdam: Elsevier, Budapest 1985; 261–269
   Google Scholar
• Gachályi B. Clinical experiences with 3-trifluoromethl-a-ethylbenzhydrol (Zixoryn), a hepatic microsomal enzyme inducing agent. Cytochrome P-450, Biochemistry, Biophysics and Induction, L. Vereczky, K. Magyar. Akademiai Kiado and Amsterdam: Elsevier, Budapest 1985; 269–271
   Google Scholar
• Gachályi B., Kaldor A., Szeberenyi Sz. m-Trifluoromethyl-a-ethylbenzhydrol: a new enzyme inducer. European Journal of Clinical Pharmacology 1978; 13: 299–302
   PubMed Web of Science ®Google Scholar
• Garcia J. Influencia del estado nutricional en el metabolismo de hormonas esteroidales. Thesis: Facultad de Quimica y Farmacia. Universidad de Chile. 1986; 1–47
   Google Scholar
• Gonzalez F. J. The molecular biology of cytochrome P-450s. Pharmacological Reviews 1989; 40(4)243–288
   Google Scholar
• Guengerich F. P., Dannan G. A., Wright S. T., Martin M. V., Kaminsky L. S. Purification and characterization of rat liver microsomal cytochromes P-450: electrophoretic, spectral, catalytic and immunochemical properties and inducibility of eight isoenzymes isolated from rats treated with phenobarbital or β-naphthoflavone. Biochemistry 1982; 21: 6019–6030
   PubMed Web of Science ®Google Scholar
• Gustafsson J.-A. Steroid hydroxylations catalysed by cytochrome P-450,. Methods in Enzymology, S. Fleischer, L. Packer. Academic Press, New York 1978; 52: 377–388
   Google Scholar
• Kamataki T., Maeda K., Yamazoe Y., Nagai T., Kato R. Sex difference of cytochrome P- 450 in the rat: purification, characterization and quantification of constitutive forms of cytochrome P-450 from liver microsomes from male and female rats. Archives of Biochemistry and Biophysics 1983; 225: 758–770
   PubMed Web of Science ®Google Scholar
• Klebovich L., Vereczckey L., Toth E. Metabolism of flumecinol in humans. Xenobiotica 1987; 17(10)1247–1258
   PubMed Web of Science ®Google Scholar
• Korányi G. Y., Boross G. Enzyminduktive Wirkung des Zixoryn (3-trifluoromethyl-a-benzhydrol) in dem Neugeboren-Ikterus. Monatsschrift für Kinderheilkunde 1985; 133: 99–101
   PubMedGoogle Scholar
• Kulcsár-Gergely J., Kulcsár A. Hormonal environment and age influencing the activity of flumecinol, a synthetic enzyme inducer. Arzneimittel-Forschung/Drug Research 1981; 31: 2101–2103
   PubMedGoogle Scholar
• Larrey D., Distlerath L. M., Dannan G. A., Wilkinson G. R., Guengerich F. P. Purification and characterization of the rat liver microsomal cytochrome P-450 involved in the 4-hydroxylation of debrisoquine, a prototype for genetic variation in oxidative drug metabolism. Biochemistry 1984; 23: 2787–2795
   PubMed Web of Science ®Google Scholar
• Lowry O. H., Rosebrough N. J., Farr A. L., Randall R. J. Protein measurements with the Folin phenol reagent. Journal of Biological Chemistry 1951; 193: 265–275
   PubMed Web of Science ®Google Scholar
• Mancilla J., Gil L. A simple, reliable and rapid HPLC method to separate and quantify androstenedione, testosterone and hydroxy-testosterones. Analytical Letters 1984; 17(B9)873–886
   Google Scholar
• Nakamura Y., Ueda S. Induction of testosterone 16/β-hydroxylase in rat liver microsomes by phenobarbital pretreatment. Biochemical and Biophysical Research Communications 1980; 93: 1014–1019
   PubMed Web of Science ®Google Scholar
• Nebert D., Adesnik M., Coon M., Estabrook R., Gonzalez F., Guengerich P., Gunsalus I., Johnson E., Kemper B., Levin W., Phillips I., Sato R., Waterman M. The P-450 gene superfamily: recommended nomenclature. DNA 1987; 6: 1–11
   PubMedGoogle Scholar
• Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification and properties. Journal of Biological Chemistry 1964; 239: 2379–2385
   PubMed Web of Science ®Google Scholar
• Pap A. Analyse de l'induction des enzymes microsomiales par le 3-trifluomethyle-a-ethylenebenzhydrol. Therapie 1979; 34: 635–640
   PubMedGoogle Scholar
• Ryan D., Iida S., Wood A. W., Thomas P. E., Lieber C. S., Levin W. Characterization of three highly purified cytochromes P-450 from hepatic microsomes of adult male rats. Journal of Biological Chemistry 1984; 259: 1239–1250
   PubMed Web of Science ®Google Scholar
• Salazar I., Litvak S., Gil L. Modulation of rat liver aryl hydrocarbon benzo(a)pyrene hydroxylase activity by nutritional effects. Journal of Toxicology and Environmental Health 1983; 11: 519–533
   PubMed Web of Science ®Google Scholar
• Sheets J. J., Estabrook R. Multiple sites of steroids hydroxylation by the liver microsomal cytochrome P-450 system from uninduced male rats. Biochemistry 1985; 24: 6591–6597
   PubMed Web of Science ®Google Scholar
• Sheets J. J., Mason J. I., Wise C. A., Estabrook R. W. Inhibition of rat liver microsomal cytochrome P-450 steroid hydroxylase reactions by imidazole antimycotic agents. Biochemical Pharmacology 1986; 35: 487–491
   PubMed Web of Science ®Google Scholar
• Shiverick K. T., Neims A. H. Multiplicity of testosterone hydroxylases in a reconstituted hepatic cytochrome P-450 system from uninduced male rats. Drug Metabolism and Disposition 1979; 7: 290–295
   PubMed Web of Science ®Google Scholar
• Comparison involving two sample means. Principles and Procedures of Statistics, R. G. D. Steel, J. H. Torrie. McGraw-Hill, New York 1960; 67–87
   Google Scholar
• Szeberényi Sz., Palosi E., Szporny L. Effect of 3-trifluoromethyl-a-ethylbenzhydrol (RGH-3332), a new enzyme inducer, on the microsomal drug metabolism. Part I. Arzneimittel-Forschung/Drug Research 1978; 28: 663–668
   PubMedGoogle Scholar
• Van Der Hoeven Th. Testosterone oxidation by rat liver microsomes: Effect of phenobarbital pretreatment and the detection of seven metabolites by HPLC. Biochemical and Biophysical Research Communications 1981; 100: 1285–1291
   PubMed Web of Science ®Google Scholar
• Vezekenyi Z., Ferenci J., Radnai B., Horvath T., Past T., Nagy L., Javor T. Human tolerance of flumecinol (Zixoryn, RGH-3332), its regime and dosage in healthy volunteers. International Journal of Clinical Pharmacology Research 1983; 3(2)77–88
   Google Scholar
• Waxman D. J. Rat hepatic cytochrome P-450 isoenzyme 2c. Identification as a male-specific, developmentally induced steroid 16-a-hydroxylase and comparison to a female-specific cytochrome P-450 isoenzymes. Journal of Biological Chemistry 1984; 259: 15481–15490
   PubMed Web of Science ®Google Scholar
• Waxman D. J. Interactions of hepatic cytochrome P-450 with steroid hormones. Biochemical Pharmacology 1988; 37: 71–84
   PubMed Web of Science ®Google Scholar
• Waxman D. J., Ko A., Walsh C. Regioselectivity and stereoselectivity of androgen hydroxylations catalized by cytochrome P-450 isozymes purified from phenobarbital-induced rat liver. Journal of Biological Chemistry 1983; 258: 11937–11947
   PubMed Web of Science ®Google Scholar
• Waxman D. J., Dannan G. A., Guengerich F. P. Regulation of rat hepatic cytochrome P-450; Age-dependent expression, hormonal imprinting and zenobiotic inducibility of sex-specific isoenzymes. Biochemistry 1985; 24: 4409–4417
   PubMed Web of Science ®Google Scholar
• Wood A. W., Ryan D. E., Thomas P. E., Levin W. Regio- and stereo-selective metabolism of two C19 steroids by five highly purified and reconstituted rat hepatic cytochrome P-450 isozymes. Journal of Biological Chemistry 1983; 258: 8839–8847
   PubMed Web of Science ®Google Scholar
• Yeowell H. N., Waxman D. J., Wadheka A., Goldstein J. A. Suppression of the constitutive, male-specific rat hepatic cytochrome P-450 2c and its mRNA by 3,4,5,3′,4′,5′- hexachlorobiphenyl and 3-methylcholanthrene. Molecular Pharmacology 1987; 32: 340–347
   PubMed Web of Science ®Google Scholar