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Metabolism of Endogenous Estrogens

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Estrogens and Antiestrogens I

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 135 / 1))

Abstract

The study of the metabolism of estradiol began many years ago; it was primarily the chemical structures of the various breakdown products that were closely described. Only later was the effort made to research further into the enzyme systems required for that breakdown and, recently, into the receptors to which the metabolites bind in the tissues.

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References

  • Adlercreutz H, Järvenpää P (1982) Assay of estrogens in human feces. J Steroid Biochem 17:639–645.

    PubMed  CAS  Google Scholar 

  • Adlercreutz H, Luukkainen T (1970) Identification and determination of estrogens in various biological materials in pregnancy. Am Clin Res 2:365–380

    CAS  Google Scholar 

  • Adlercreutz H, Martin F (1976) Estrogen in human pregnancy feces. Acta Endocrinol 83:410–419.

    PubMed  CAS  Google Scholar 

  • Adlercreutz H, Ervast HS, Tenhunen A, Tikkanen MJ (1973) Gas chromatographic and mass spectrometric studies on estrogens in bile. Acta Endocrinol 73:543–554.

    PubMed  CAS  Google Scholar 

  • Adlercreutz H, Martin F, Tikkanen MJ, Pulkinnen M (1975) Effect of ampicillin administration on the excretion of twelve estrogens in pregnancy urine. Acta Endocrinol 80:551–557.

    PubMed  CAS  Google Scholar 

  • Adlercreutz H, Martin F, Pulkkinen M, Dencker H, Rimer U, Sjoberg NO, Tikkanen MJ (1976) Intestinal metabolism of estrogens. J Clin Endocrinol Metab 43:497–509.

    PubMed  CAS  Google Scholar 

  • Adlercreutz H, Fotsis T, Bannwart C, Hamalainen E, Bloigu S, Ollus A (1986) Urinary estrogen profile determination in young Finnish vegetarian and omnivorous women. J Steroid Biochem 24:289–296.

    PubMed  CAS  Google Scholar 

  • Adlercreutz H, Gorbach SL, Goldin BR, Woods MN, Dwyer JT, Hämäläinen E (1994) Estrogen metabolism and excretion in Oriental and Caucasian women. J Natl Cancer Inst 86:1076–1082.

    PubMed  CAS  Google Scholar 

  • Anderson KE, Kappas A, Conney AH, Bradlow HL, Fishman J (1984) The influence of dietary protein and carbohydrate on the principal oxidative biotransformations of estradiol in normal subjects. J Clin Endocrinol Metab 59:103–107.

    PubMed  CAS  Google Scholar 

  • Auborn KJ, Woodworth C, Dipaolo J, Bradlow HL (1991) The interaction between HPV infection and estrogen metabolism in cervical carcinogenesis. Int J Cancer 49:867–869.

    PubMed  CAS  Google Scholar 

  • Ball P, Knuppen R (1978) Formation of 2-and 4-hydroxyestrogens in the brain, pituitary and liver of the human fetus. J Clin Endocrinol Metab 47:732–737.

    PubMed  CAS  Google Scholar 

  • Ball P, Knuppen R (1980) Catecholoestrogens (2-and 4-hydroxyoestrogens). Chemistry, biogenesis, metabolism, occurence and physiological significance. Acta Endocrinol 232[Suppl]:1–127.

    CAS  Google Scholar 

  • Ball P, Stubenrauch G, Knuppen R (1977) Metabolism of 2-methoxy and 4-methoxye-strone in man in vivo. J Steroid Biochem 8:989–993.

    PubMed  CAS  Google Scholar 

  • Banger M, Hiemke C, Knuppen R, Ball P, Haupt M, Wiedemann K (1990) Formation and metabolism of catecholestrogens in depressed patients. Biol Psychiatry 28:685–696.

    PubMed  CAS  Google Scholar 

  • Barnea ER, MacLusky NJ, Purdy R, Naftolin F (1988) Estrogen hydroxylase activity in the human placenta at term. J Steroid Biochem 31:253–255.

    PubMed  CAS  Google Scholar 

  • Baron JA (1984) Smoking and estrogen-related disease. Am J Epidemiol 119:9–22.

    PubMed  CAS  Google Scholar 

  • Bates GW, Edman CD, Porter JC, MacDonald PC (1977) Metabolism of catecholestrogen by human erythrocytes. J Clin Endocrinol Metab 45:1120–1123.

    PubMed  CAS  Google Scholar 

  • Beischer N, Brown J, Parkinson P, Walstab J (1991) Urinary estriol assay for monitoring fetoplacental function. Aust N Z J Obstet Gynaecol 31:1–8.

    PubMed  CAS  Google Scholar 

  • Berg FD, Kuss E (1992) Serum concentrations and urinary excretion of classical estrogens, catecholestrogens and 2-methoxyestrogens in normal pregnancy. Arch Gynecol Obstet 251:17–27.

    PubMed  CAS  Google Scholar 

  • Biswas A, Chaudhury A, Chattoraj SC, Dale SL (1991) Do catechol estrogens participate in the initiation of labor? Am J Obstet Gynecol 165:984–987.

    PubMed  CAS  Google Scholar 

  • Bradfield CA, Bjeldanes LF (1984) Effect of dietary indole-3-carbinol on intestinal and hepatic monooxygenase glutathione S-transferase and epoxide hydrolase activities in the rat. Food Chem Toxicol 22:977–982.

    PubMed  CAS  Google Scholar 

  • Bradlow HL, Hershcopf RJ, Martucci CP, Fishman J (1985) Estradiol 16a hydroxyla-tion in the mouse correlates with mammary tumor incidence and presence of mammary tumor virus: a possible model for the hormonal etiology of breast cancer in humans. Proc Natl Acad Sci USA 82:6295–6299.

    PubMed  CAS  Google Scholar 

  • Bradlow HL, Arcuri F, Blasi L, Castagnetta L (1995a) Effect of serum albumin on estrogen metabolism in human cancer cell lines. Mol Cell Endocrinol 115:221–225.

    PubMed  CAS  Google Scholar 

  • Bradlow HL, Davis DL, Lin G, Sepkovic DW, Tiwari R (1995b) Effects of pesticides on the ratio of 16alpha-/2-hydroxyestrone: a biological marker of breast cancer risk. Environ Health Perspect 103:147–150.

    PubMed  CAS  Google Scholar 

  • Bradlow HL, Michnovicz JJ, Wong GYC, Harper MP, Miller D, Osborne MP (1995c) Long term responses of women to indole-3-carbinol or a high fiber diet. Cancer Prev Biomarkers Epidemiol 3:591–595.

    Google Scholar 

  • Bradlow HL, Sepkovic DW, Telang NT, Osborne MP (1995d) Indole-3-carbmol. A novel approach to breast cancer prevention. Ann NY Acad Sci 768:180–200.

    PubMed  CAS  Google Scholar 

  • Bradlow HL, Telang NT, Sepkovic DW, Osborne MP (1996) 2-hydroxyestrone: the good estrogen. J Endocrinol 150:5259–5265.

    Google Scholar 

  • Carruba G, Miceli MD, Camito L, Farruggio R, Sorci CMG, Oliveri G, Amodio R, DiFalco M, D’Amico D, Castagnetta LAM (1996) Multiple estrogen functions in human prostate cancer cells. Ann NY Acad Sci 784:70–84.

    PubMed  CAS  Google Scholar 

  • Castagnetta LA, LoCasto M, Granata OM, Polito L, Calabro M, LoBue A, Bellavia V, Carruba G (1996) Estrogen content and metabolism in human breast tumor tissues and cells. Ann NY Acad Sci 784:314–324.

    PubMed  CAS  Google Scholar 

  • Chao ST, Omiecinski CJ, Namkung MJ, Nelson SD, Dvorchik BH, Juchau MR (1981) Catechol estrogen formation in placental and fetal tissues of humans, macaques, rats and rabbits. Dev Pharmacol Ther 2:1–16.

    PubMed  CAS  Google Scholar 

  • Chao TC (1996) Female sex hormones and the immune system. Chang Keng I Hsueh 19:95–106.

    PubMed  CAS  Google Scholar 

  • Chen C, Malone KE, Prunty JA, Daling JR (1996) Measurement of urinary estrogen metabolites using a monoclonal enzyme-linked immunoassay kit: assay performance and feasibility for epidemiological studies. Cancer Epidemiol Biomarkers Prev 5:727–732.

    PubMed  CAS  Google Scholar 

  • Coll DA, Rosen CA, Auborn K, Potsic WP, Bradlow HL (1997) Treatment of recurrent respiratory papillomatosis with indole-3-carbinol. Am J Otolaryngol 18:283–285.

    PubMed  CAS  Google Scholar 

  • Cutolo M, Castagnetta L (1996) Immunomodulatory mechanisms mediated by sex hormones in rheumatoid arthritis. Ann NY Acad Sci 784:237–251.

    PubMed  CAS  Google Scholar 

  • De Crée C, Ball P, Seidlitz B (1997a) Plasma 2-hydroxycatecholestrogen responses to acute submaximal and maximal exercise. J Appl Physiol 82:364–370.

    PubMed  Google Scholar 

  • De Cree C, Ball P, Seidlitz B, Van Kranenburg G, Geurten P, Keizer HA (1997b) Effects of a training programm on resting plasma 2-hydroxycatecholestrogen levels in eumenorrheic women. J Appl Physiol 83:1551–1556.

    PubMed  Google Scholar 

  • De Cree C, Van Kranenburg G, Geurten P, Fujimori Y, Keizer HA (1997c) 4-hydroxycatecholestrogen metabolism responses to exercise and training: possible implications for menstrual cycle irregularities and breast cancer. Fertil Steril 67:505–516.

    PubMed  Google Scholar 

  • Diczfalusy E (1969) Steroid metabolism in the human feto-placental unit. Acta Endocrinol 61:649–664.

    PubMed  CAS  Google Scholar 

  • Dorgan JF, Judd JT, Longcope C, Brown C, Schatzkin A, Clevidence BA, Campbell WS, Nair PP, Franz C, Kahle L, Taylor PR (1996) Effect of dietary fat and fiber on plasma and urine androgens and estrogens in man: a controlled feeding study. Am J Clin Nutr 64:850–855.

    PubMed  CAS  Google Scholar 

  • Dunn JF, Merriam GR, Eil C, Kono S, Loriaux DL, Nisula BC (1980) Testosterone-estradiol binding globulin binds to 2-hydroxyestradiol with greater affinity than to testosterone. J Clin Endocrinol Metab 51:404–406.

    PubMed  CAS  Google Scholar 

  • Emons G, Merriam GR, Pfeiffer D, Loriaux DL, Ball P, Knuppen R (1987) Metabolism of exogenous 4-and 2-hydroxyestradiol in the human male. J Steroid Biochem 28:499–504.

    PubMed  CAS  Google Scholar 

  • Essman E, Abramson A (1984) Estrogen binding sites on membranes from human laryngeal papilloma. Int J Cancer 33:33–36.

    PubMed  CAS  Google Scholar 

  • Fishman J, Martucci C (1980a) Biological properties of 16α-hydroxyestrone: Implications in estrogen physiology and pathophysiology. J Clin Endocrinol Metabol 51:611–615.

    CAS  Google Scholar 

  • Fishman J, Martucci C (1980b) Dissociation of biological activities in metabolites of estradiol. In: McLachlan JA (ed) Estrogens in the environment. Elsevier, North-Holland, pp 131–145.

    Google Scholar 

  • Fishman J, Bradlow HL, Gallagher TF (1960) Oxidative metabolism of estradiol. J. Biol Chem 235:3104–3107.

    PubMed  CAS  Google Scholar 

  • Fishman J, Brown JB, Hellman L, Zumoff B, Gallagher TF (1962a) Estrogen metabolism in normal and pregnant women. J Biol Chem 237:1489–1494.

    PubMed  CAS  Google Scholar 

  • Fishman J, Hellman L, Zumoff B, Gallagher TF (1962b) Influence of thyroid hormone on estrogen metabolism in man. J Clin Endocr 22:389–392.

    PubMed  CAS  Google Scholar 

  • Fishman J, Hellman L, Zumoff B, Gallagher TF (1965) Effect of thyroid on hydroxylation of estrogen in man. J Clin Endocrinol Metab 25:365–368.

    PubMed  CAS  Google Scholar 

  • Fishman J, Boyar RM, Hellman L (1972) The system estradiol — estrone; a sex difference in oxidation of estradiol in man. J Clin Endocrinol Metab 34:989–995.

    PubMed  CAS  Google Scholar 

  • Fishman J, Boyar RM, Hellman L (1975) Influence of body weight on estradiol metabolism in young women. J Clin Endocrinol Metab 41:984–991.

    Google Scholar 

  • Fishman J, Bradlow HL, Schneider J, Anderson KE, Kappas A (1980) Radiometric analysis of biological oxidations in man: sex differences in estradiol metabolism. Proc Natl Acad Sci USA 77:4957–4960.

    PubMed  CAS  Google Scholar 

  • Fishman J, Schneider J, Hershcopf RJ, Bradlow HL (1984) Increased estrogen 16-alpha hydroxylase activity in women with breast and endometrial cancer. J Steroid Biochem 20:1077–1081.

    PubMed  CAS  Google Scholar 

  • Fishman J, Osborne P, Telang NT (1995) The role of estrogen in mammary carcinogenesis. Ann NY Acad Sci 768:91–100.

    PubMed  CAS  Google Scholar 

  • Fotsis T, Järvenpää P, Adlercreutz H (1980a) Identification of 4-hydroxyestriol in pregnancy urine. J Clin Endocrinol Metab 51:148–151.

    PubMed  CAS  Google Scholar 

  • Fotsis T, Järvenpää P, Adlercreutz H (1980b) Purification of urine for quantification of the complete estrogen profile. J Steroid Biochem 12:503–508.

    PubMed  CAS  Google Scholar 

  • Fotsis T, Zhang Y, Pepper MS, Adlercreutz H, Montesano R, Nawroth PP, Schweigerer L (1994) The endogenous estrogen metabolite 2-methoxyoestradiol inhibits angio-genesis and suppresses tumour growth. Nature 368:237–239.

    PubMed  CAS  Google Scholar 

  • Galbraith RA, Michnovicz JJ (1989) The effects of Cimetidine on the oxidative metabolism of estradiol. N Engl J Med 321:269–274.

    PubMed  CAS  Google Scholar 

  • Galbraith RA, Michnovicz JJ (1993) Omeprazole fails to alter the cytochrome P450-dependent 2-hydroxylation of estradiol in male volunteers. Pharmacology 47:8–12.

    PubMed  CAS  Google Scholar 

  • Gelbke HP, Knuppen R (1976) The excretion of five different 2-hydroxy estrogen monomethyl ethers in human pregnancy urine. J Steroid Biochem 7:457–463.

    PubMed  CAS  Google Scholar 

  • Gelbke HP, Böttger M, Knuppen R (1975a) Excretion of 2-hydroxyestrone in urine throughout human pregnancies. J Clin Endocrinol Metab 41:744–750.

    PubMed  CAS  Google Scholar 

  • Gelbke HP, Hoogen H, Knuppen R (1975b) Identification of 2-hydroxyestradiol and the pattern of catechol estrogens in human pregnancy urine. J Steroid Biochem 6:1187–1191.

    PubMed  CAS  Google Scholar 

  • Goldin BR, Adlercreutz H, Gorbach SL, Warram JH, Dwyer JT, Swenson L, Woods MN (1982) Estrogen excretion patterns and plasma levels in vegetarian and omnivorous women. N Engl J Med 307:1542–1547.

    PubMed  CAS  Google Scholar 

  • Goldin BR, Adlercreutz H, Gorbach SL, Woods MN, Dwyer JT, Conlon T, Bohn E, Gershoff SN (1986) The relationship between estrogen levels and diets of Caucasian American and Oriental immigrant women. Am J Clin Nutr 44:945–953.

    PubMed  CAS  Google Scholar 

  • Gorbach SL, Goldin BR (1987) Diet and the excretion and enterohepatic cycling of estrogens. Prev Med 16:525–531.

    PubMed  CAS  Google Scholar 

  • Gordon S, Cantrall EW, Cekleniak WP, Albers HJ, Mauer S, Stolar SM, Bernstein S (1964) Steroid and lipid metabolism. The hypocholesteremic effect of estrogen metabolites. Steroids 4:267–271.

    CAS  Google Scholar 

  • Goyache FM, Gutierrez M, Hidalgo A, Cantabrana B (1995) Non-genomic effects of catecholestrogens in the in vitro rat uterine contraction. Gen Pharmacol 26:219–223.

    PubMed  CAS  Google Scholar 

  • Han X, Liehr JG (1994) DNA single-strand breaks in kidneys of Syrian hamsters treated with steroidal estrogens: hormone-induced free radical damage preceding renal malignancy. Carcinogenesis 15:997–1000.

    PubMed  CAS  Google Scholar 

  • Hellman L, Zumoff B, Fishman J, Gallagher TF (1970) Estradiol metabolism in total extrahepatic biliary obstruction. J Clin Endocrinol 30:161–165.

    CAS  Google Scholar 

  • Herrmann WM, Beach RC (1978) The psychotropic properties of estrogens. Pharmacopsychiatry 11:164–176.

    CAS  Google Scholar 

  • Hershcopf RJ, Bradlow HL (1987) Obesity, diet, endogenous estrogens and the risk of hormone-sensitive cancer. Am J Clin Nutr 45:283–289.

    PubMed  CAS  Google Scholar 

  • Hobkirk R (1985) Steroid sulfotransferases and steroid sulfatases. Characteristics and biological roles. Can J Biochem Cell Biol 63:1127–1144.

    PubMed  CAS  Google Scholar 

  • Iverson SL, Shen L, Anlar N, Bolton JL (1996) Bioactivation of estrone and its catechol metabolites to quinoid-glutathione conjugates in rat liver microsomes. Chem Res Toxicol 9:492–499.

    PubMed  CAS  Google Scholar 

  • Kabat GC, Chang CJ, Sparano JA, Sepkovic DW, Hu XP, Khalil A, Rosenblatt R, Bradlow HL (1997) Urinary estrogen metabolites and breast cancer: a case-control study. Cancer Epidemiol Biomarkers Prev 6:505–509.

    PubMed  CAS  Google Scholar 

  • Kall MA, Vang O, Clausen J (1996) Effects of dietary broccoli on human in vivo drug metabolizing enzymes: evaluation of caffeine, oestrone and chlorzoxazone metabolism. Carcinogenesis 17:793–799.

    PubMed  CAS  Google Scholar 

  • Kono S, Merriam GR, Brandon DD, Loriaux DL, Lipsett MB (1982) Radioimmunoassay and metabolism of the catechol estrogen 2-hydroxyestradiol. J Clin Endocrinol Metab 54:150–154.

    PubMed  CAS  Google Scholar 

  • Kowalczyk TD, Cabaniss ML, Cusmano D (1998) Association of low unconjugated estriol and the second trimester and adverse pregnancy outcome. Obstet Gynecol 91:396–400.

    PubMed  CAS  Google Scholar 

  • Lahita RG (1996) The connective tissue diseases and the overall influence of gender. Int J Fertil Menopausal Stud 41:156–165.

    PubMed  CAS  Google Scholar 

  • Lahita RG, Bradlow HL, Kunkel HG, Fishman J (1979) Alterations of estrogen metabolism in systemic lupus erythematosus. Arthritis Rheum 22:1195–1198.

    PubMed  CAS  Google Scholar 

  • Lahita RG, Bradlow HL, Kunkel HG, Fishman J (1981) Increased 16α-hydroxylation of estradiol in systemic lupus erythematosus. J Clin Endocrinol Metab 53:174–178.

    PubMed  CAS  Google Scholar 

  • Lahita RG, Bradlow HL, Fishman J, Kunkel HG (1982) Abnormal estrogen and androgen metabolism in the human with systemic lupus erythematosus. Am J Kidney Dis 2:206–211.

    PubMed  CAS  Google Scholar 

  • Lahita RG, Bucala R, Bradlow HL, Fishman J (1984) Determination of 16α-hydroxyestrone by radioimmunoassay in systemic lupus erythematosus. Arthritis Rheum 28:1122–1127.

    Google Scholar 

  • Lim SK, Won YJ, Lee JH, Kwon SH, Lee EJ, Kim KR, Lee HC, Huh KB, Chung BC (1997) Altered hydroxylation of estrogen in patients with postmenopausal osteopenia. J Clin Endocrinol Metab 82:1001–1006.

    PubMed  CAS  Google Scholar 

  • Lippert TH, Seeger H, Mueck AO (1998) Estradiol metabolism during oral and transdermal estradiol replacement therapy in postmenopausal women. Horm Metab Res 30:598–600.

    PubMed  CAS  Google Scholar 

  • Lippert TH, Seeger H, Mueck AO (1999) Estrogens and prevention of cardiovascular disease: the role of estradiol metabolites. Climacteric 7:296–301.

    Google Scholar 

  • Longcope C, Femino A, Flood C, Williams KIH (1982) Metabolic clearance rate and conversion ratios of 3H-hydroxyestrone in normal men. J Clin Endocrinol Metab 54:374–380.

    PubMed  CAS  Google Scholar 

  • Longcope C, Flood C, Femino A, Williams KIH (1983) Metabolism of 2-methoxyestrone in normal men. J Clin Endocrinol Metab 57:277–282.

    PubMed  CAS  Google Scholar 

  • Longcope C, Gorbach S, Godlin B, Woods M, Dwyer J, Morrill A, Warram J (1987) The effect of a low fat diet on estrogen metabolism. J Clin Endocrinol Metab 64:1246–1250.

    PubMed  CAS  Google Scholar 

  • Martucci CP, Fishman J (1993) P450 enzymes of estrogen metabolism. Pharmacol Ther 57:237–257.

    PubMed  CAS  Google Scholar 

  • McEwen BS, Davis PG, Parsons B, Pfaff DW (1979) The brain as target for steroid hormone action. Ann Rev Neurosci 2:65–112.

    PubMed  CAS  Google Scholar 

  • Merriam GR, Brandon DD, Kono S, Davies SE, Loriaux DL, Lipsett MB (1980) Rapid metabolic clearance of the catechol estrogen 2-hydroxyestrone. J Clin Endocrinol Metab 51:1211–1213.

    PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Bradlow HL (1990) Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst 82:947–949.

    PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Bradlow HL (1991) Altered estrogen metabolism and excretion in humans following consumption of indole-3-carbmol. Nutr Cancer 16:59–66.

    PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Galbraith RA (1990) Effects of exogenous thyroxine on C-2 and C-16 hydroxylation of estradiol in humans. Steroids 55:22–26.

    PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Galbraith RA (1991) Cimetidine inhibits catechol estrogen metabolism in women. Metabolism 40:170–174.

    PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Hershcopf RJ, Naganuma H, Bradlow HL, Fishman J (1986) Increased 2-hydroxylation of estradiol as a possible mechanism for the anti-estrogenic effect of cigarette smoking. N Engl J Med 315:1305–1309.

    PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Naganuma H, Hershcopf RJ, Bradlow HL, Fishman J (1988) Increased urinary catechol estrogen excretion in female smokers. Steroids 52:69–83.

    PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Hershcopf RJ, Haley NJ, Bradlow HL, Fishman J (1989) Cigarette smoking alters hepatic estrogen metabolism in men: implication for atherosclerosis. Metabolism 38:537–541.

    PubMed  CAS  Google Scholar 

  • Michnovicz JJ, Adlercreutz H, Bradlow HL (1997) Changes in levels of urinary estrogen metabolites after oral indole-3-carbinol treatment in humans. J Natl Cancer Inst 89:718–723.

    PubMed  CAS  Google Scholar 

  • Mueck AO, Seeger H, Gräser T, Oettel M, Lippert TH (1998) Effect of postmenopausal hormone replacement therapy (HRT) and of oral contraceptives (OC) on estradiol metabolism. Naunyn Schmiedebergs Arch Pharmacol 358:R788.

    Google Scholar 

  • Musey PI, Kright K, Preedy JRK, Collins DC (1979) Formation and metabolism of steroid conjugates: effect of conjugation on excretion and tissue distribution. In: Hobkirk R (ed) Steroid biochemistry, vol IL CRC Press Boca Raton, pp 81-132.

    Google Scholar 

  • Newfield L, Goldsmith A, Bradlow HL, Auborn K (1993) Estrogen metabolism and human papilloma virus-induced tumors of the larynx. Anticancer Res 13:227–242.

    Google Scholar 

  • Osborne MP, Karmali RA, Hershcopf RJ, Bradlow HL, Fishman J (1988) Omega-3 fatty acids: modulation of estrogen metabolism and potential for breast cancer prevention. Cancer Invest 8:531–629.

    Google Scholar 

  • Osborne MP, Bradlow HL, Wong GY, Telang NT (1993) Upregulation of estradiol C16alpha-hydroxylation in human breast tissue: a potential biomarker of breast cancer risk. J Natl Cancer Inst 85:1917–1920.

    PubMed  CAS  Google Scholar 

  • Pasagian-Macaulay A, Meilahn EN, Bradlow HL, Sepkovic DW, Buhari AM, Simkin-Silverman L, Wing RR, Kuller LH (1996) Urinary markers of estrogen metabolism 2-and 16alpha-hydroxylation in premenopausal women. Steroids 61:461–467.

    PubMed  CAS  Google Scholar 

  • Pulkkinen MO, Willman K (1973) Reduction of maternal estrogen excretion by neomycin. Am J Obstet Gynecol 115:1153.

    PubMed  CAS  Google Scholar 

  • Purohit A, Reed MJ, Morris NC, Williams GJ, Potter BVL (1996) Regulation and inhibition of steroid sulfatase activity in breast cancer. Ann NY Acad Sci 184:40–49.

    Google Scholar 

  • Rosen CA, Woodson GE, Tompson JW, Hengesteg AP, Bradlow HL (1998) Preliminary results of the use of indole-3-carbinol for recurrent respiratory papillomatosis. Otolaryngol Head Neck Surg 118:810–815.

    PubMed  CAS  Google Scholar 

  • Schneider J, Kinne D, Fracchia A, Pierce V, Anderson KE, Bradlow HL, Fishman J (1982) Abnormal oxidative metabolism of estradiol in women with breast cancer. Proc Natl Acad Sci USA 79:3047–3051.

    PubMed  CAS  Google Scholar 

  • Schneider J, Bradlow HL, Strain G, Levin J, Anderson K, Fishman J (1983) Effects of obesity on estradiol metabolism: decreased formation of non-uterotropic metabolites. J Clin Endocrinol Metab 56:973–978.

    PubMed  CAS  Google Scholar 

  • Sepkovic DW, Bradlow HL, Ho G, Hankinson SE, Gong L, Osborne MP, Fishman J (1995) Estrogen metabolite ratios and risk assessment of hormone-related cancers: assay validation and prediction of cervical cancer risk. Ann NY Acad Sci 768:312–316.

    PubMed  CAS  Google Scholar 

  • Siiteri PK, MacDonald PC (1966) Placental estrogen biosynthesis during human pregnancy. J Clin Endocrinol Metab 26:751–761.

    PubMed  CAS  Google Scholar 

  • Simpson ER, Zhao Y (1996) Estrogen biosynthesis in adipose. Significance in breast cancer development. Ann NY Acad Sci 784:18–26.

    PubMed  CAS  Google Scholar 

  • Snow R, Barbieri R, Frisch R (1989) Estrogen 2-hydroxylase oxidation and menstrual function among elite oarswomen. J Clin Endocrinol Metab 69:369–376.

    PubMed  CAS  Google Scholar 

  • Speroff L, Glass RH, Kase NG, Bohnet HG (1993) Gynäkologische Endokrinologie und steriles Paar. Diesbach Verlag, Berlin, pp 271–301.

    Google Scholar 

  • Steinberg BM, Abramson AL (1985) Laryngeal papillomas. Clin Dermatol 3:130–138.

    PubMed  CAS  Google Scholar 

  • Tabor MW, Coats E, Sainsbury M, Shertzer HG (1991) Antioxidation potential of indole compounds — structure activity studies. Adv Exp Med Biol 283:833–836.

    PubMed  CAS  Google Scholar 

  • Tiwari RK, Guo L, Bradlow HL, Telang NT, Osborne MP (1994) Selective responsiveness of human breast cancer cells to indole-3-carbinol, a chemopreventive agent. J Natl Cancer Inst 86:126–131.

    PubMed  CAS  Google Scholar 

  • Tyler CW, Webster LA, Ory HW, Rubin GL (1985) Endometrial cancer: how does cigarette smoking influence the risk of women under age 55 years having this tumor? Am J Obstet Gynecol 151:899–905.

    PubMed  Google Scholar 

  • Van Vallenhoven RF, McGuire JL (1994) Estrogen, progesterone and testosterone: can they be used to treat autoimmune diseases? Cleve Clin J Med 61:276–284.

    Google Scholar 

  • Willman K, Pulkkinen MO (1971) Reduced maternal plasma and urinary estriol during ampicillin treatment. Am J Obstet Gynecol 109:893–896.

    PubMed  CAS  Google Scholar 

  • Yager JD, Liehr JG (1996) Molecular mechanism of estrogen carcinogenesis. Annu Rev Pharmacol Toxicol 36:203–232.

    PubMed  CAS  Google Scholar 

  • Zhu BT, Conney AH (1998) Functional role of estrogen metabolism in target cells: review and perspectives. Carcinogenesis 19:1–27.

    PubMed  Google Scholar 

  • Zhu BT, Liehr JG (1993) Inhibition of the catechol-O-methyltransferase-catalyzed O-methylation of 2-and 4-hydroxyestradiol by catecholamines. Implications for the mechanism of estrogen-induced carcinogenesis. Arch Biochem Biophys 304:248–256.

    PubMed  CAS  Google Scholar 

  • Zumoff B, Fishman J, Cassouto J, Hellman L, Gallagher TF (1966) Estradiol transformation in men with breast cancer. J Clin Endocrinol 26:960–966.

    CAS  Google Scholar 

  • Zumoff B, Fishman J, Cassouto J, Gallagher TF, Hellman L (1968a) Influence of age and sex on normal estradiol metabolism. J Clin Endocrinol 28:937–941.

    CAS  Google Scholar 

  • Zumoff B, Fishman J, Gallagher TF, Hellman L (1968b) Estradiol metabolism in liver cirrhosis. J Clin Invest 47:20–25.

    PubMed  CAS  Google Scholar 

  • Zumoff B, Fishman J, Levin J, Gallagher TF, Hellman L (1970) Reversible reproduction of the abnormal estradiol metabolism of biliary obstruction by administration of norethandrolone. J Clin Endocrinol 30:598–601.

    CAS  Google Scholar 

  • Zumoff B, Freed SZ, Levin J, Whitmore WF, Hellman L, Fishman J, Kukushima DK (1980) Metabolism of 3H-estradiol in men with prostate cancer. Eur J Cancer 16:219–221.

    PubMed  CAS  Google Scholar 

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Authors
  1. T. H. Lippert
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  2. H. Seeger
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  3. A. O. Mueck
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Editor information

Editors and Affiliations

  1. Leiter Forschung und Entwicklung Jenapharm GmbH & Co. KG, Otto-Schott-Str. 15, D-07745, Jena, Germany

    Michael Oettel

  2. Leiter Forschung, Fertilitätskontrolle und Hormontherapie, Schering Aktiengesellschaft, D-13342, Berlin, Germany

    Ekkehard Schillinger

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© 1999 Springer-Verlag Berlin Heidelberg

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Lippert, T.H., Seeger, H., Mueck, A.O. (1999). Metabolism of Endogenous Estrogens. In: Oettel, M., Schillinger, E. (eds) Estrogens and Antiestrogens I. Handbook of Experimental Pharmacology, vol 135 / 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-58616-3_12

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  • DOI: https://doi.org/10.1007/978-3-642-58616-3_12

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-63667-7

  • Online ISBN: 978-3-642-58616-3

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