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Original

Can 19-nortestosterone derivatives be aromatized in the liver of adult humans? Are there clinical implications?

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Pages 344-353 | Received 17 Dec 2006, Accepted 22 Feb 2007, Published online: 03 Jul 2009

References

  • Kuhl H. Pharmacology of estrogens and progestogens: influence of different routes of administration. Climacteric 2005; 8(Suppl 1)3–63
  • Wiegratz I, Sänger N, Kuhl H. Formation of 7α-methyl-ethinyl estradiol during treatment with tibolone. Menopause 2002; 4: 293–295
  • Davis S R, Simpson E R. Letter to the Editor. Kuhl H, Wiegratz I. In reply. Menopause 2003; 10: 105–107
  • Zacharia L C, Jackson E K, Kloosterboer H J, Imthurn B, Dubey R K. Conversion of tibolone to 7a-methyl-ethinyl estradiol using gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry: interpretation and clinical implications. Menopause 2006; 13: 926–934
  • Timmer C J, Verheul H AM, Doorstam D P. Pharmacokinetics of tibolone in early and late postmenopausal women. Br J Clin Pharmacol 2002; 54: 101–106
  • Kuhl H, Wiegratz I. Letter to the Editor. Menopause 2007; 14: 331–334
  • Brueggemeier R W, Hackett J C, Diaz-Cruz E S. Aromatase inhibitors in the treatment of breast cancer. Endocr Rev 2005; 26: 331–345
  • Simpson E R, Clyne C, Rubin G, et al. Aromatase – a brief overview. Annu Rev Physiol 2002; 64: 93–127
  • Vos R ME, Krebbers S FM, Verhoeven C HJ, et al. The in vivo human metabolism of tibolone. Drug Metab Dispos 2002; 30: 106–112
  • Kuhnz W, Heuner A, Hümpel M, et al. In vivo conversion of norethisterone and norethisterone acetate to ethinyl estradiol in postmenopausal women. Contraception 1997; 56: 379–385
  • de Gooyer M E, Oppers-Tiemissen H M, Leysen D, et al. Tibolone is not converted by human aromatase to 7α-methyl-17α-ethynylestradiol (7α-MEE): analyses with sensitive bioassays for estrogens and androgens and with LC-MSMS. Steroids 2003; 68: 235–243
  • Raobaikady B, Parsons M FC, Reed M J, et al. Lack of aromatization of the 3-keto-4-ene metabolite of tibolone to an estrogenic derivative. Steroids 2006; 71: 639–646
  • Yamamoto T, Yoshiji S, Yasuda J, et al. Aromatization of norethindrone to ethynylestradiol in human adult liver. Endocrinol Jpn 1986; 33: 527–531
  • Urabe M, Yamamoto T, Yoshiji S, et al. Aromatization of norethindrone to ethynylestradiol in human adult liver. Steroids 1987; 50: 607–608
  • Yamamoto T, Kitawaki J, Shiroshita K, et al. The confirmation of norethindrone aromatization in primary human hepatocytes by the vitafiber-II cell culture system. Acta Obstet Gynaec Jpn 1988; 40: 87–89
  • Reed M J, Ross M S, Lai L C, et al. In vivo conversion of norethisterone to ethynyloestradiol in perimenopausal women. J Steroid Biochem Molec Biol 1990; 37: 301–303
  • Klehr-Bathmann I, Kuhl H. Formation of ethinylestradiol in postmenopausal women during continuous treatment with a combination of estradiol, estriol and norethisterone acetate. Maturitas 1995; 21: 245–250
  • Beier S, Düsterberg B, El Etreby M F, . Toxicology of hormonal fertility-regulating agents. Endocrine Mechanisms in Fertility Regulation, G Benagiano, E Diczfalusy, et al. Raven Press, New York 1983; 261–346
  • Kloosterboer H J. Tibolone and its metabolites: pharmacology, tissue specificity and effects in animal model of tumors. Gynecol Endocrinol 1997; 11(Suppl 1)63–68
  • Thompson R M, Horning E C. Aromatization of the A-ring of norethynodrel, a steroidal oral contraceptive, during trimethylsilylation. Steroids Lipids Res 1973; 4: 135–142
  • Gomes M PV, Deitcher S R. Risk of venous thromboembolic disease associated with hormonal contraceptives and hormone replacement therapy. Arch Intern Med 2004; 164: 1965–1976
  • Conard J, Plu-Bureau G, Bahi N, et al. Progestogen-only contraception in women at high risk of venous thromboembolism. Contraception 2004; 70: 437–441
  • Bodine P VN, Harris H A, Lyttle R, et al. Estrogenic effects of 7a-methyl-ethinylestradiol: a newly discovered tibolone metabolite. Steroids 2002; 67: 681–686
  • Cummings S R. LIFT study is discontinued. BMJ 2006; 332: 667
  • Wassertheil-Smoller S, Hendrix S L, Limacher M, et al. Effect of estrogen plus progestin on stroke in postmenopausal women. JAMA 2003; 289: 2673–2684
  • Million Women Study Collaborators. Endometrial cancer and hormone-replacement therapy in the Million Women Study. Lancet 2005; 365: 1543–1551
  • Kuhl H, Stevenson J. The effect of medroxyprogesterone acetate on estrogen-dependent risks and benefits – an attempt to interpret the Women's Health Initiative results. Gynecol Endocrinol 2006; 22: 303–317
  • de Vries C S, Bromley S E, Thomas H, et al. Tibolone and endometrial cancer. A cohort and nested case-control study in the UK. Drug Safety 2005; 28: 241–249
  • Bjarnason N H. Endometrial cancer and hormone-replacement therapy. Lancet 2005; 366: 200–201
  • Whitehead M I, Townsend P T, Pryse-Davies J, et al. Effects of various types and dosages of progestogens on the postmenopausal endometrium. J Reprod Med 1982; 27: 539–548
  • Klaassens A HA, van Wijk F H, Hanifi-Moghaddam P, et al. Histological and immunohistochemical evaluation of postmenopausal endometrium after 3 weeks of treatment with tibolone, estrogen only, or estrogen plus progestogen. Fertil Steril 2006; 86: 352–361
  • Perez-Medina T, Bajo-Arenas J, Haya J, et al. Tibolone and risk of endometrial polyps: a prospective, comparative study with hormone therapy. Menopause 2003; 10: 534–537
  • Schoonen W GEJ, Deckers G H, de Gooijer M E, et al. Hormonal properties of norethisterone, 7α-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol 2000; 74: 213–222
  • Dimitrakis C, Zhou J, Wang J, et al. A physiologic role for testosterone in limiting estrogenic stimulation of the breast. Menopause 2003; 10: 292–298
  • Dimitrakis C, Jones R A, Liu A, Bondy C A. Breast cancer incidence in postmenopausal women using testosterone in addition to usual hormone therapy. Menopause 2004; 11: 531–535
  • Million Women Study Collaborators. Breast cancer and hormone-replacement therapy in the Million Women Study. Lancet 2003; 362: 419–427
  • Stahlberg C, Tonnes Pedersen A, Lynge E, et al. Increased risk of breast cancer following different regimens of hormone replacement therapy frequently used in Europe. Br J Cancer 2004; 109: 721–727
  • Farish E, Barnes J F, Fletcher C D, et al. Effects of tibolone on serum lipoprotein and apolipoprotein levels compared with a cyclic estrogen/progestogen regimen. Menopause 1999; 6: 98–104
  • Milner M, Sinnott M, Gasparo D, et al. Climacteric symptoms, gonadotrophins, sex steroids, and binding proteins with conjugated equine estrogen-progestin and tibolone over two years. Menopause 1996; 3: 208–213
  • Larsson-Cohn U, Fahraeus L, Wallentin L, et al. Effects of the estrogenicity of levonorgestrel/ethinylestradiol combinations on the lipoprotein status. Acta Obstet Gynecol Scand Suppl 1982; 105: 37–40
  • Phillips A, Hahn D W, Klimek S, et al. A comparison of the potencies and activities of progestogens used in contraceptives. Contraception 1987; 36: 181–192
  • de Beer F, Smelt A HM, van Vark L C, et al. The effect of tibolone on the lipoprotein profile of postmenopausal women with type III hyperlipoproteinemia. J Intern Med 2002; 251: 148–155
  • Kushwaha R S, Hazzard W R, Gagne C, et al. Type III hyperlipoproteinemia: paradoxical hypolipidemic response to estrogen. Ann Intern Med 1977; 87: 517–525

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