Tibolone: a steroid with a tissue-specific mode of action

Vies van der, 1987, Pharmacological studies with (7 alpha, 17 alpha)-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3-one (Org OD14), Maturitas, Suppl. 1, 15, 10.1016/0378-5122(87)90039-9 De Visser, 1984, Endocrinological studies with (7 alpha, 17 alpha)-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3-one (Org OD14), Arzneim Forsch/Drug Res., 34, 1010 Labrie, 1991, At the cutting edge: intracinology, Mol. Cell. Endocr., 78, C113, 10.1016/0303-7207(91)90116-A McKenna, 1999, Nuclear receptor coregulators: cellular and molecular biology, Endocr. Rev., 20, 321, 10.1210/er.20.3.321 Improta-Brears, 1999, Estrogen-induced activation of mitogen-activated protein kinase requires mobilization of intracellular calcium, Proc. Natl. Acad. Sci. U.S.A., 96, 4686, 10.1073/pnas.96.8.4686 Sandker, 1994, Metabolism of three pharmacologically active drugs in isolated human and rat hepatocytes: analysis of interspecies variability and comparison with metabolism in vivo, Xenobiotica, 24, 143, 10.3109/00498259409043228 Kunhz, 1993, Pharmacokinetics of estradiol, free and total estrone in young women following single intravenous and oral administration of 17β-estradiol, Arzneim Forsch/Drug Res., 43, 966 Vree, 1998, Enterohepatic cycling and pharmacokinetics of oestradiol in postmenopausal women, J. Pharmacol., 50, 857, 10.1111/j.2042-7158.1998.tb04000.x Timmer, 1999, Bioequivalence assessment of three different estradiol formulations in postmenopausal women in an open, randomized, single dose, 3-way cross-over study, Eur. J. Drug Metab. Pharmacokin., 24, 47, 10.1007/BF03190010 Lievertz, 1987, Pharmacology and pharmacokinetics of estrogens, Am. J. Obstet. Gynecol., 156, 1289, 10.1016/0002-9378(87)90166-9 Murugesan, 1973, In vitro metabolism of [6,7-3H] norethynodrel in the human endometrium and the myometrium, Acta Endocr., 74, 576 Palmer, 1969, Metabolism of antifertility steroids. I. Norethynodrel, J. Pharmacol. Exp. Therap., 167, 207 Sudaram, 1995, Different patterns of metabolism determine the relative anabolic activity of 19-norandrogens, J. Steroid Biochem. Mol. Biol., 53, 253, 10.1016/0960-0760(95)00056-6 L. Delbressine, M. de Gooyer, H.J. Kloosterboer, Sulphated metabolites of tibolone show sulphatase inhibiting activity, in: Endocrine Society Meeting, Toronto 2000, Abstract 1639. Tang, 1993, Human endometrial 3β-hydroxysteroid dehydrogenase/isomerase can locally reduce intrinsic estrogenic/progestagenic activity ratios of a steroidal drug (Org OD14), J. Steroid Biochem. Mol. Biol., 45, 345, 10.1016/0960-0760(93)90003-F Schoonen, 2000, Hormonal properties of norethisterone, 7α-methyl-norethisterone and their derivates, J. Steroid Biochem. Mol. Biol., 74, 213, 10.1016/S0960-0760(00)00125-4 Bjarnason, 1996, Tibolone: prevention of bone loss in late postmenopausal women, J. Clin. Endocr. Metab., 81, 2419, 10.1210/jc.81.7.2419 Bjarnason, 1997, The response in spinal bone mass to tibolone treatment is related to bone turnover in elderly women, Bone, 20, 151, 10.1016/S8756-3282(96)00335-3 Berning, 1996, Effects of two doses of tibolone on trabecular and cortical bone loss in early postmenopausal women: a two-year randomized placebo-controlled study, Bone, 19, 395, 10.1016/S8756-3282(96)00219-0 Dören, 1999, An assessment of hormone replacement therapy to prevent postmenopausal osteoporosis, Osteopor. Int., Suppl. 2, S53, 10.1007/PL00004162 Delmas, 1997, Effects of raloxifene on bone mineral density, serum cholesterol concentrations, and uterine endometrium in postmenopausal women, N. Engl. J. Med., 337, 1641, 10.1056/NEJM199712043372301 Selby, 1996, Alendronate treatment for osteoporosis: a review of the clinical evidence, Osteopor. Int., 6, 419, 10.1007/BF01629572 Ederveen, 1999, Tibolone, a steroid with a tissue-specific hormonal profile, completely prevents ovariectomy-induced bone loss in sexually mature rat, J. Bone Miner. Res., 14, 1963, 10.1359/jbmr.1999.14.11.1963 Ederveen, 1999, Tibolone exerts an estrogenic effect on bone leading to prevention of bone loss and reduction in bone resorption in ovariectomized rats, Osteopor. Int., 8, 95 Ederveen, 1996, A sixteen month treatment with tibolone prevents loss of bone and maintains biomechanical quality of cortical and trabecular bone in ovariectomized rats, J. Bone Miner. Res., 11, S350 Albertazzi, 1998, Tibolone a review, Maturitas, 30, 295, 10.1016/S0378-5122(98)00059-0 Rymer, 1998, The effects of tibolone, Gynecol. Endocr., 12, 213, 10.3109/09513599809015548 Jelinek, 1984, A primate model of human postmenopausal hot flushes, J. Clin. Endocr. Metab., 59, 1224, 10.1210/jcem-59-6-1224 Berendsen, 1999, Effect of tibolone in two animal models for menopausal hot flushes, Climacteric, 2, 322 Genazzani, 1984, Effects of Org OD14 on pituitary and peripheral beta-endorphin in castrated rats and postmenopausal women, Maturitas, Suppl. 1, 35 Genazzani, 1987, Effects of Org OD14 on pituitary and peripheral β endorphin in castrated rats and postmenopausal women, Maturitas, Suppl. 1, 35, 10.1016/0378-5122(87)90041-7 Hoeger, 1999, The use of androgens in menopause, Clin. Obstet. Gynecol., 42, 883, 10.1097/00003081-199912000-00016 Guennoun, 1995, A key enzyme in the biosynthesis of neurosteroids, 3β-hydroxysterid dehydrogenase/Δ5-Δ4-isomerase (3β-HSD), is expressed in rat brain, Mol. Brain Res., 30, 287, 10.1016/0169-328X(95)00016-L Milewick, 1993, 3β-Hydroxysteroid dehydrogenase activity in tissues of human fetus determined with 5a-androstane-3β, 17β-diol and dehydroepiandrosterone as substrates, J. Steroid Biochem. Mol. Biol., 45, 525, 10.1016/0960-0760(93)90169-W Abdallah, 1986, Organon OD14 (tibolone) and menopausal dynamic hormone profiles, Maturitas, 8, 81, 10.1016/0378-5122(86)90011-3 Markiewicz, 1990, In vitro evaluation of estrogenic, estrogen antagonistic and progestagenic effects of a steroidal drug (Org OD14) and its metabolites on human endometrium, J. Steroid Biochem., 35, 535, 10.1016/0022-4731(90)90196-Y Beral, 1997, On behalf of the collaborative group on hormonal factors in breast cancer, Lancet, 350, 1047 Kloosterboer, 1994, Effect of progestagens and Org OD14 in in vitro and in vivo tumor models, J. Steroid Biochem. Mol. Biol., 49, 311, 10.1016/0960-0760(94)90273-9 Gompel, 1997, The effect of tibolone on proliferation, differentiation and apoptosis in normal breast cells, Gynecol. Endocrinol., 1, 77, 10.3109/09513599709152586 Pasqualini, 1996, Concentration of estrone, estradiol, estrone sulfate and evaluation of sulfatase and aromatase activities in pre- and postmenopausal breast cancer patients, J. Clin. Endocr. Metab., 31, 1460, 10.1210/jc.81.4.1460 Duncan, 1993, Inhibition of estrone sulfatase activity by estrone-3-0-methylthiophosphonate: a potential therapeutic agent in breast cancer, Cancer Res., 53, 298 Chetrite, 1997, Effect of tibolone (Org OD14) and its metabolites on estrone sulphatase activity in MCF-7 and T-47D mammary cancer cells, Anticancer Res., 17, 135 Chetrite, 1999, Effects of Org OD14 (Livial®) and its metabolites on 17β-hydroxysteroid dehydrogenase activity in hormone-dependent MCF-7 and T-47D breast cancer cells, Anticancer Res., 19, 261 Valdivia, 2000, Mammographic density in postmenopausal women treated with tibolone, estriol or conventional hormone replacement therapy, Clin. Drug Invest., 20, 101, 10.2165/00044011-200020020-00005 Kloosterboer, 1999, Tibolone inhibits sulfatase activity in breast but not in bone, Climacteric, 2, 322 M.E. de Gooyer, H.J. Kloosterboer, A.G.H. Ederveen, Tibolone: a tissue-specific sulphatase inhibitor, in: Proceedings of 14th International Symposium of the J. Steroid Biochem. Mol. Biol. Quecbec, 2000, Abstract 43P. A. Purohit, B. Malani, S.P. Newman, Inhibition of oestrone sulphatase activity by tibolone (Org OD14) and its metabolites, in: Proceedings of 14th International Symposium of the J. Steroid Biochem. Mol. Biol. Quecbec, 2000, Abstract 46P. Rijpkema, 1990, Effects of postmenopausal oestrongen-progestagen replacement therapy on serum lipids and lipoproteins: a review, Maturitas, 12, 259, 10.1016/0378-5122(90)90007-S Bjarnason, 1997, Tibolone: Influence on markers of cardiovascular disease, J. Clin. Endocr. Metab., 82, 1752, 10.1210/jc.82.6.1752 Farish, 1999, Effects of tibolone on serum lipoprotein and apolipoprotein levels compared with cyclical estrogen/progestagen regimen, Menopause, 6, 98, 10.1097/00042192-199906020-00005 Miettinen, 1981, Lowered HDL cholesterol and incidence of ischaemic heart disease, Lancet, 2, 478, 10.1016/S0140-6736(81)90817-5 van Wersch, 1994, The effect of two regimens of hormone replacement therapy on the haemostatic profile in postmenopausal women, Eur. J. Clin. Chem. Clin. Biochem., 32, 449 Winkler, 2000, Effects of tibolone and continuous combined hormone replacement therapy on parameters in the clothing cascade: a multicenter, double-blind, randomized study, Fertil. Steril., 74, 10, 10.1016/S0015-0282(00)00587-2 Walker, 1985, The effect of the synthetic steroid Org OD14 on fibrinolysis and blood lipids in postmenopausal women, Thromb. Haemost., 53, 303, 10.1055/s-0038-1661302 Zandberg, 1998, Tibolone prevents atherosclerotic lesion formation in cholesterol-fed, ovariectomized rabbits, Arterioscler. Thromb. Vasc. Biol., 18, 1844, 10.1161/01.ATV.18.12.1844 Simoncini, 2000, Tibolone inhibits leucocyte adhesion molecule expression in human endothelial cells, Mol. Cell. Endocr., 162, 87, 10.1016/S0303-7207(00)00206-9