메뉴 건너뛰기




Volumn 10, Issue 4, 2007, Pages 344-353

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

Author keywords

19 Nortestosterone derivatives; 7 methyl ethinylestradiol; Aromatization; Clinical implications; Human liver; Tibolone

Indexed keywords

7ALPHA METHYL ETHINYLESTRADIOL; 7ALPHA METHYL NORETHISTERONE; ANDROGEN; ANDROSTENEDIONE; AROMATASE; CHLORMADINONE ACETATE; CONJUGATED ESTROGEN; ESTRADIOL; ESTRADIOL PLUS NORETHISTERONE ACETATE; ESTRONE; ETHINYLESTRADIOL; MEDROXYPROGESTERONE ACETATE; NANDROLONE DERIVATIVE; NORETHISTERONE; NORETHISTERONE ACETATE; NORETYNODREL; ORAL CONTRACEPTIVE AGENT; STEROID; TESTOSTERONE; TIBOLONE; UNCLASSIFIED DRUG;

EID: 34547157219     PISSN: 13697137     EISSN: 14730804     Source Type: Journal    
DOI: 10.1080/13697130701380434     Document Type: Review
Times cited : (22)

References (43)
  • 1
    • 24144485432 scopus 로고    scopus 로고
    • Pharmacology of estrogens and progestogens: Influence of different routes of administration
    • Kuhl H. Pharmacology of estrogens and progestogens: influence of different routes of administration. Climacteric 2005;8(Suppl 1):3-63
    • (2005) Climacteric , vol.8 , Issue.SUPPL. 1 , pp. 3-63
    • Kuhl, H.1
  • 2
    • 0036308069 scopus 로고    scopus 로고
    • Formation of 7α-methyl-ethinyl estradiol during treatment with tibolone
    • Wiegratz I, Sänger N, Kuhl H. Formation of 7α-methyl-ethinyl estradiol during treatment with tibolone. Menopause 2002;4:293-5
    • (2002) Menopause , vol.4 , pp. 293-295
    • Wiegratz, I.1    Sänger, N.2    Kuhl, H.3
  • 3
    • 13444266718 scopus 로고    scopus 로고
    • Davis SR, Simpson ER. Letter to the Editor. Kuhl H, Wiegratz I. In reply. Menopause 2003;10:105-7
    • Davis SR, Simpson ER. Letter to the Editor. Kuhl H, Wiegratz I. In reply. Menopause 2003;10:105-7
  • 4
    • 33751051583 scopus 로고    scopus 로고
    • Conversion of tibolone to 7a-methyl-ethinyl estradiol using gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry: Interpretation and clinical implications
    • Zacharia LC, Jackson EK, Kloosterboer HJ, Imthurn B, Dubey RK. Conversion of tibolone to 7a-methyl-ethinyl estradiol using gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry: interpretation and clinical implications. Menopause 2006;13:926-34
    • (2006) Menopause , vol.13 , pp. 926-934
    • Zacharia, L.C.1    Jackson, E.K.2    Kloosterboer, H.J.3    Imthurn, B.4    Dubey, R.K.5
  • 5
    • 0036041453 scopus 로고    scopus 로고
    • Pharmacokinetics of tibolone in early and late postmenopausal women
    • Timmer CJ, Verheul HAM, Doorstam DP. Pharmacokinetics of tibolone in early and late postmenopausal women. Br J Clin Pharmacol 2002;54:101-6
    • (2002) Br J Clin Pharmacol , vol.54 , pp. 101-106
    • Timmer, C.J.1    Verheul, H.A.M.2    Doorstam, D.P.3
  • 6
    • 34250614303 scopus 로고    scopus 로고
    • Letter to the Editor
    • Kuhl H, Wiegratz I. Letter to the Editor. Menopause 2007;14:331-4
    • (2007) Menopause , vol.14 , pp. 331-334
    • Kuhl, H.1    Wiegratz, I.2
  • 10
    • 0031431370 scopus 로고    scopus 로고
    • In vivo conversion of norethisterone and norethisterone acetate to ethinyl estradiol in postmenopausal women
    • Kuhnz W, Heuner A, Hümpel M, et al. In vivo conversion of norethisterone and norethisterone acetate to ethinyl estradiol in postmenopausal women. Contraception 1997;56:379-85
    • (1997) Contraception , vol.56 , pp. 379-385
    • Kuhnz, W.1    Heuner, A.2    Hümpel, M.3
  • 11
    • 0037333156 scopus 로고    scopus 로고
    • 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
    • de Gooyer ME, Oppers-Tiemissen HM, 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;68:235-43
    • (2003) Steroids , vol.68 , pp. 235-243
    • de Gooyer, M.E.1    Oppers-Tiemissen, H.M.2    Leysen, D.3
  • 12
    • 33646787774 scopus 로고    scopus 로고
    • Lack of aromatization of the 3-keto-4-ene metabolite of tibolone to an estrogenic derivative
    • Raobaikady B, Parsons MFC, Reed MJ, et al. Lack of aromatization of the 3-keto-4-ene metabolite of tibolone to an estrogenic derivative. Steroids 2006;71:639-46
    • (2006) Steroids , vol.71 , pp. 639-646
    • Raobaikady, B.1    Parsons, M.F.C.2    Reed, M.J.3
  • 13
    • 0022996139 scopus 로고
    • Aromatization of norethindrone to ethynylestradiol in human adult liver
    • Yamamoto T, Yoshiji S, Yasuda J, et al. Aromatization of norethindrone to ethynylestradiol in human adult liver. Endocrinol Jpn 1986;33:527-31
    • (1986) Endocrinol Jpn , vol.33 , pp. 527-531
    • Yamamoto, T.1    Yoshiji, S.2    Yasuda, J.3
  • 14
    • 38249034854 scopus 로고
    • Aromatization of norethindrone to ethynylestradiol in human adult liver
    • Urabe M, Yamamoto T, Yoshiji S, et al. Aromatization of norethindrone to ethynylestradiol in human adult liver. Steroids 1987;50:607-8
    • (1987) Steroids , vol.50 , pp. 607-608
    • Urabe, M.1    Yamamoto, T.2    Yoshiji, S.3
  • 15
    • 0023728231 scopus 로고
    • The confirmation of norethindrone aromatization in primary human hepatocytes by the vitafiber-II cell culture system
    • 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;40:87-9
    • (1988) Acta Obstet Gynaec Jpn , vol.40 , pp. 87-89
    • Yamamoto, T.1    Kitawaki, J.2    Shiroshita, K.3
  • 16
    • 0025094009 scopus 로고
    • In vivo conversion of norethisterone to ethynyloestradiol in perimenopausal women
    • Reed MJ, Ross MS, Lai LC, et al. In vivo conversion of norethisterone to ethynyloestradiol in perimenopausal women. J Steroid Biochem Molec Biol 1990;37:301-3
    • (1990) J Steroid Biochem Molec Biol , vol.37 , pp. 301-303
    • Reed, M.J.1    Ross, M.S.2    Lai, L.C.3
  • 17
    • 0028964025 scopus 로고
    • Formation of ethinylestradiol in postmenopausal women during continuous treatment with a combination of estradiol, estriol and norethisterone acetate
    • 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;21:245-50
    • (1995) Maturitas , vol.21 , pp. 245-250
    • Klehr-Bathmann, I.1    Kuhl, H.2
  • 18
    • 0003890668 scopus 로고
    • Toxicology of hormonal fertility-regulating agents
    • Benagiano G, Diczfalusy E, eds, New York: Raven Press
    • Beier S, Düsterberg B, El Etreby MF, et al. Toxicology of hormonal fertility-regulating agents. In Benagiano G, Diczfalusy E, eds. Endocrine Mechanisms in Fertility Regulation. New York: Raven Press, 1983:261-346
    • (1983) Endocrine Mechanisms in Fertility Regulation , pp. 261-346
    • Beier, S.1    Düsterberg, B.2    El Etreby, M.F.3
  • 19
    • 0001939751 scopus 로고    scopus 로고
    • Tibolone and its metabolites: Pharmacology, tissue specificity and effects in animal model of tumors
    • Kloosterboer HJ. Tibolone and its metabolites: pharmacology, tissue specificity and effects in animal model of tumors. Gynecol Endocrinol 1997;11(Suppl 1):63-8
    • (1997) Gynecol Endocrinol , vol.11 , Issue.SUPPL. 1 , pp. 63-68
    • Kloosterboer, H.J.1
  • 20
    • 0015715785 scopus 로고
    • Aromatization of the A-ring of norethynodrel, a steroidal oral contraceptive, during trimethylsilylation
    • Thompson RM, Horning EC. Aromatization of the A-ring of norethynodrel, a steroidal oral contraceptive, during trimethylsilylation. Steroids Lipids Res 1973;4:135-42
    • (1973) Steroids Lipids Res , vol.4 , pp. 135-142
    • Thompson, R.M.1    Horning, E.C.2
  • 21
    • 6344286114 scopus 로고    scopus 로고
    • Risk of venous thromboembolic disease associated with hormonal contraceptives and hormone replacement therapy
    • Gomes MPV, Deitcher SR. Risk of venous thromboembolic disease associated with hormonal contraceptives and hormone replacement therapy. Arch Intern Med 2004;164:1965-76
    • (2004) Arch Intern Med , vol.164 , pp. 1965-1976
    • Gomes, M.P.V.1    Deitcher, S.R.2
  • 22
    • 8444231757 scopus 로고    scopus 로고
    • Progestogen-only contraception in women at high risk of venous thromboembolism
    • Conard J, Plu-Bureau G, Bahi N, et al. Progestogen-only contraception in women at high risk of venous thromboembolism. Contraception 2004;70:437-41
    • (2004) Contraception , vol.70 , pp. 437-441
    • Conard, J.1    Plu-Bureau, G.2    Bahi, N.3
  • 23
    • 0036317099 scopus 로고    scopus 로고
    • Estrogenic effects of 7a-methyl-ethinylestradiol: A newly discovered tibolone metabolite
    • Bodine PVN, Harris HA, Lyttle R, et al. Estrogenic effects of 7a-methyl-ethinylestradiol: a newly discovered tibolone metabolite. Steroids 2002;67:681-6
    • (2002) Steroids , vol.67 , pp. 681-686
    • Bodine, P.V.N.1    Harris, H.A.2    Lyttle, R.3
  • 24
    • 33645227472 scopus 로고    scopus 로고
    • LIFT study is discontinued
    • Cummings SR. LIFT study is discontinued. BMJ 2006;332:667
    • (2006) BMJ , vol.332 , pp. 667
    • Cummings, S.R.1
  • 25
    • 0037534909 scopus 로고    scopus 로고
    • Effect of estrogen plus progestin on stroke in postmenopausal women
    • Wassertheil-Smoller S, Hendrix SL, Limacher M, et al. Effect of estrogen plus progestin on stroke in postmenopausal women. JAMA 2003;289:2673-84
    • (2003) JAMA , vol.289 , pp. 2673-2684
    • Wassertheil-Smoller, S.1    Hendrix, S.L.2    Limacher, M.3
  • 26
    • 18144421167 scopus 로고    scopus 로고
    • Million Women Study Collaborators. Endometrial cancer and hormone-replacement therapy in the Million Women Study. Lancet 2005;365:1543-51
    • Million Women Study Collaborators. Endometrial cancer and hormone-replacement therapy in the Million Women Study. Lancet 2005;365:1543-51
  • 27
    • 33745340959 scopus 로고    scopus 로고
    • The effect of medroxyprogesterone acetate on estrogen-dependent risks and benefits - an attempt to interpret the Women's Health Initiative results
    • 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;22:303-17
    • (2006) Gynecol Endocrinol , vol.22 , pp. 303-317
    • Kuhl, H.1    Stevenson, J.2
  • 28
    • 14944350750 scopus 로고    scopus 로고
    • Tibolone and endometrial cancer. A cohort and nested case-control study in the UK
    • de Vries CS, Bromley SE, Thomas H, et al. Tibolone and endometrial cancer. A cohort and nested case-control study in the UK. Drug Safety 2005;28:241-9
    • (2005) Drug Safety , vol.28 , pp. 241-249
    • de Vries, C.S.1    Bromley, S.E.2    Thomas, H.3
  • 29
    • 24944579648 scopus 로고    scopus 로고
    • Endometrial cancer and hormone-replacement therapy
    • Bjarnason NH. Endometrial cancer and hormone-replacement therapy. Lancet 2005;366:200-1
    • (2005) Lancet , vol.366 , pp. 200-201
    • Bjarnason, N.H.1
  • 30
    • 0020418320 scopus 로고
    • Effects of various types and dosages of progestogens on the postmenopausal endometrium
    • Whitehead MI, Townsend PT, Pryse-Davies J, et al. Effects of various types and dosages of progestogens on the postmenopausal endometrium. J Reprod Med 1982;27:539-48
    • (1982) J Reprod Med , vol.27 , pp. 539-548
    • Whitehead, M.I.1    Townsend, P.T.2    Pryse-Davies, J.3
  • 31
    • 33746373011 scopus 로고    scopus 로고
    • Histological and immunohistochemical evaluation of postmenopausal endometrium after 3 weeks of treatment with tibolone, estrogen only, or estrogen plus progestogen
    • Klaassens AHA, van Wijk FH, 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;86:352-61
    • (2006) Fertil Steril , vol.86 , pp. 352-361
    • Klaassens, A.H.A.1    van Wijk, F.H.2    Hanifi-Moghaddam, P.3
  • 32
    • 2342576969 scopus 로고    scopus 로고
    • Tibolone and risk of endometrial polyps: A prospective, comparative study with hormone therapy
    • 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;10:534-7
    • (2003) Menopause , vol.10 , pp. 534-537
    • Perez-Medina, T.1    Bajo-Arenas, J.2    Haya, J.3
  • 33
    • 0034668706 scopus 로고    scopus 로고
    • Hormonal properties of norethisterone, 7α-methyl-norethisterone and their derivatives
    • Schoonen WGEJ, Deckers GH, de Gooijer ME, et al. Hormonal properties of norethisterone, 7α-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol 2000;74:213-22
    • (2000) J Steroid Biochem Mol Biol , vol.74 , pp. 213-222
    • Schoonen, W.G.E.J.1    Deckers, G.H.2    de Gooijer, M.E.3
  • 34
    • 0038786584 scopus 로고    scopus 로고
    • A physiologic role for testosterone in limiting estrogenic stimulation of the breast
    • Dimitrakis C, Zhou J, Wang J, et al. A physiologic role for testosterone in limiting estrogenic stimulation of the breast. Menopause 2003;10:292-8
    • (2003) Menopause , vol.10 , pp. 292-298
    • Dimitrakis, C.1    Zhou, J.2    Wang, J.3
  • 35
    • 14944359093 scopus 로고    scopus 로고
    • Breast cancer incidence in postmenopausal women using testosterone in addition to usual hormone therapy
    • Dimitrakis C, Jones RA, Liu A, Bondy CA. Breast cancer incidence in postmenopausal women using testosterone in addition to usual hormone therapy. Menopause 2004;11:531-5
    • (2004) Menopause , vol.11 , pp. 531-535
    • Dimitrakis, C.1    Jones, R.A.2    Liu, A.3    Bondy, C.A.4
  • 36
    • 0042018741 scopus 로고    scopus 로고
    • Million Women Study Collaborators. Breast cancer and hormone-replacement therapy in the Million Women Study. Lancet 2003;362:419-27
    • Million Women Study Collaborators. Breast cancer and hormone-replacement therapy in the Million Women Study. Lancet 2003;362:419-27
  • 37
    • 1642419529 scopus 로고    scopus 로고
    • Increased risk of breast cancer following different regimens of hormone replacement therapy frequently used in Europe
    • 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;109:721-7
    • (2004) Br J Cancer , vol.109 , pp. 721-727
    • Stahlberg, C.1    Tonnes Pedersen, A.2    Lynge, E.3
  • 38
    • 0033035087 scopus 로고    scopus 로고
    • Effects of tibolone on serum lipoprotein and apolipoprotein levels compared with a cyclic estrogen/progestogen regimen
    • Farish E, Barnes JF, Fletcher CD, et al. Effects of tibolone on serum lipoprotein and apolipoprotein levels compared with a cyclic estrogen/progestogen regimen. Menopause 1999;6: 98-104
    • (1999) Menopause , vol.6 , pp. 98-104
    • Farish, E.1    Barnes, J.F.2    Fletcher, C.D.3
  • 39
    • 0000954207 scopus 로고    scopus 로고
    • Climacteric symptoms, gonadotrophins, sex steroids, and binding proteins with conjugated equine estrogen-progestin and tibolone over two years
    • 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;3:208-13
    • (1996) Menopause , vol.3 , pp. 208-213
    • Milner, M.1    Sinnott, M.2    Gasparo, D.3
  • 40
    • 0020010166 scopus 로고
    • Effects of the estrogenicity of levonorgestrel/ethinylestradiol combinations on the lipoprotein status
    • 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
    • (1982) Acta Obstet Gynecol Scand Suppl , vol.105 , pp. 37-40
    • Larsson-Cohn, U.1    Fahraeus, L.2    Wallentin, L.3
  • 41
    • 0023271854 scopus 로고
    • A comparison of the potencies and activities of progestogens used in contraceptives
    • Phillips A, Hahn DW, Klimek S, et al. A comparison of the potencies and activities of progestogens used in contraceptives. Contraception 1987;36:181-92
    • (1987) Contraception , vol.36 , pp. 181-192
    • Phillips, A.1    Hahn, D.W.2    Klimek, S.3
  • 42
    • 0036167274 scopus 로고    scopus 로고
    • The effect of tibolone on the lipoprotein profile of postmenopausal women with type III hyperlipoproteinemia
    • de Beer F, Smelt AHM, van Vark LC, et al. The effect of tibolone on the lipoprotein profile of postmenopausal women with type III hyperlipoproteinemia. J Intern Med 2002;251:148-55
    • (2002) J Intern Med , vol.251 , pp. 148-155
    • de Beer, F.1    Smelt, A.H.M.2    van Vark, L.C.3
  • 43
    • 0017752657 scopus 로고
    • Type III hyperlipoproteinemia: Paradoxical hypolipidemic response to estrogen
    • Kushwaha RS, Hazzard WR, Gagne C, et al. Type III hyperlipoproteinemia: paradoxical hypolipidemic response to estrogen. Ann Intern Med 1977;87:517-25
    • (1977) Ann Intern Med , vol.87 , pp. 517-525
    • Kushwaha, R.S.1    Hazzard, W.R.2    Gagne, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.