Epristeride is a selective and specific uncompetitive inhibitor of human steroid 5α-reductase isoform 2

1983 Imperato-McGinley, 1979, Male pseudohermaphroditism secondary to 5α-reductase deficiency—a model for the role of androgens in both the development of the male phenotype and the evolution of male gender identity, J. Steroid Biochem., 11, 637, 10.1016/0022-4731(79)90093-1 Peterson, 1977, Male pseudohermaphroditism due to steroid 5α-reductase deficiency, Am. J. Med., 62, 170, 10.1016/0002-9343(77)90313-8 Brooks, 1986, 5α-Reductase inhibitory and anti-androgenic activities of some 4-azasteroids in the rat, Steroids, 47, 1, 10.1016/0039-128X(86)90072-3 Blohm, 1986, Pharmacological induction of 5α-reductase deficiency in the rat: Separation of testosterone-mediated and 5α-dihydrotestosterone-mediated effects, Endocrinology, 119, 959, 10.1210/endo-119-3-959 Metcalf, 1989, Inhibitors of steroid 5α-reductase in benign prostatic hyperplasia, male pattern baldness and acne, Trends Pharmac. Sci., 10, 491, 10.1016/0165-6147(89)90048-5 Metcalf, 1989, Potent inhibition of human steroid 5α-reductase (EC 1.3.1.30) by 3-androsten-3-carboxylic acids, Bioorg. Chem., 17, 372, 10.1016/0045-2068(89)90038-2 Holt, 1990, Inhibition of steroid 5α-reductase by unsaturated 3-carboxysteroids, J. Med. Chem., 33, 943, 10.1021/jm00165a010 Levy, 1990, Inhibition of rat liver steroid 5α-reductase by 3-androstene-3-carboxylic acids: Mechanism of enzyme-inhibitor interaction, Biochemistry, 29, 2815, 10.1021/bi00463a026 Levy, 1991, 3-Phosphinic acid and 3-phosphonic acid steroids as inhibitors of steroid 5α-reductase: Species comparison and mechanistic studies, Bioorg. Chem., 19, 245, 10.1016/0045-2068(91)90050-Y Andersson, 1989, Expression, cloning, and regulation of steroid 5α-reductase: an enzyme essential for male sexual differentiation, J. Biol. Chem., 264, 16249, 10.1016/S0021-9258(18)71614-1 Andersson, 1990, Structural and biochemical properties of cloned and expressed human and rat steroid 5α-reductases, 87, 3640 Andersson, 1991, Deletion of steroid 5α-reductase 2 gene in male pseudohermaphroditism, Nature, 354, 159, 10.1038/354159a0 Jenkins, 1992, Genetic and pharmacological evidence for more than one human steroid 5α-reductase, J. Clin. Invest., 89, 293, 10.1172/JCI115574 Chirgwin, 1979, Isolation of biologically active ribonucleic acid from sources enriched in ribonucleases, Biochemistry, 18, 5294, 10.1021/bi00591a005 Mullis, 1987, Specific synthesis of DNA in vitro via a polymerase-catalyzed chain reaction, Methods Enzym., 155, 335, 10.1016/0076-6879(87)55023-6 Bergsma, 1991, The cyclophilin multigene family of peptidyl-prolyl isomerases, J. Biol. Chem., 266, 23204, 10.1016/S0021-9258(18)54484-7 Kosak, 1986, Point mutations define a sequence flanking the AUG initiator codon that modulates translation by eukaryotic ribosomes, Cell, 44, 283, 10.1016/0092-8674(86)90762-2 Trill, 1990, Expression and characterization of finger protease (FP); a mutant tissue-type plasminogen activator (t-PA) with improved pharmacokinetics, Fibrinolysis, 4, 131, 10.1016/S0268-9499(05)80044-X Liang, 1985, Species differences in prostatic steroid 5α-reductases of rat, dog and human, Endocrinology, 26, 571, 10.1210/endo-117-2-571 Levy, 1987, Inhibition of 3(17)β-hydroxysteroid dehydrogenase from Pseudomonas testosteroni by steroidal A ring fused pyrazoles, Biochemistry, 26, 2270, 10.1021/bi00382a030 Brandt, 1989, 3β-Hydroxy-Δ5-steroid dehydrogenase/3-keto-Δ5-steroid isomerase from bovine adrenals: Mechanism of inhibition by 3-oxo-4-aza steroid and kinetic mechanism of the dehydrogenase, Biochemistry, 28, 140, 10.1021/bi00427a021 Brady, 1978, Study of microsomal mixed function oxidative demethylation and deformylation of 4-methyl and 4-hydroxymethylene sterols, J. Biol. Chem., 253, 3101, 10.1016/S0021-9258(17)40808-8 Levy M.A. and Holt D.A.: Unpublished results. Cleland, 1979, The statistical analysis of enzyme kinetic data, Adv. Enzym., 29, 1 Okuda, 1984, Purification and characterization of Δ4-3-ketosteroid 5β-reductase, J. Biol. Chem., 259, 7519, 10.1016/S0021-9258(17)42821-3 Penning, 1984, Purification and properties of a 3α-hydroxysteroid dehydrogenase of rat liver cytosol and its inhibition by anti-inflammatory drugs, Biochem. J., 222, 601, 10.1042/bj2220601 Reed, 1976, Kinetic properties of human placental aromatase, J. Biol. Chem., 251, 1625, 10.1016/S0021-9258(17)33694-3 Greway, 1989, Inhibition and time-dependent inactivation of human placental aromatase by 3-oxo-17β-carboxamido steroids, J. Steroid Biochem., 33, 573, 10.1016/0022-4731(89)90043-5 Nilsson, 1988, Effects of estrogen and growth hormone on steroid sulfatase activity and estrogen binding in rat liver, J. Steroid Biochem., 29, 293, 10.1016/0022-4731(88)90029-5 Thompson, 1963, The sterols of liver and carcass of 20,25-diaza-cholesterol-fed rats, Steroids, 2, 99, 10.1016/S0039-128X(63)80039-2 Ator, 1992, Synthesis, specificity, and antifungal activity of inhibitors of Candida albicansΔ24-sterol methyltransferase, J. Med. Chem., 35, 100, 10.1021/jm00079a012 Dixon, 1953, The determination of enzyme inhibitor constants, Biochem. J., 55, 170, 10.1042/bj0550170 Leavitt, 1974, Specific progesterone receptor in the hamster uterus. Physiologic properties and regulation during the estrous cycle, Endocrinology, 9, 1041, 10.1210/endo-94-4-1041 Leavitt, 1977, Regulation of progesterone receptor formation by estrogen action, Ann. N.Y. Acad. Sci., 286, 210, 10.1111/j.1749-6632.1977.tb29418.x Nichols, 1992, Pharmacokinetics and pharamacodynamics of SK&F 105657 in healthy elderly male subjects, Clin. Pharmac. Ther., PII-32, 154 Levy, 1989, Interaction between rat prostatic steroidal 5α-reductase and 3-carboxy-17β-substituted steroids: novel mechanism of enzyme inhibition, J. Steroid Biochem., 34, 571, 10.1016/0022-4731(89)90148-9 Gibbons, 1986, Biochemistry of Cholesterol Biosynthesis, 131 Lamb, 1992, Prostatic involution in rats induced by a novel 5α-reductase inhibitor, SK&F 105657: Role for testosterone in the androgenic response, Endocrinology, 130, 685, 10.1210/en.130.2.685 Lamb, 1992, Response of rat and human prostatic cancers to the novel 5α-reductase inhibitor SK&F 105657, Prostate, 21, 15, 10.1002/pros.2990210103 Manson J.M., Brown T.J. and Wier P.J.: Unpublished results.