메뉴 건너뛰기




Volumn 35, Issue 10, 2007, Pages 1942-1948

Elimination of antiestrogenic effects of active tamoxifen metabolites by glucuronidation

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYTAMOXIFEN; ANTIESTROGEN; DRUG METABOLITE; ENDOXIFEN; ESTRADIOL; ESTROGEN RECEPTOR; MESSENGER RNA; PROGESTERONE RECEPTOR; TAMOXIFEN; UNCLASSIFIED DRUG;

EID: 34748865637     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.016279     Document Type: Article
Times cited : (48)

References (37)
  • 1
    • 0019132163 scopus 로고
    • Evidence for the metabolic activation of nonsteroidal antioestrogens: A study of structure-activity relationships
    • Allen KE, Clark ER, and Jordan VC (1980) Evidence for the metabolic activation of nonsteroidal antioestrogens: a study of structure-activity relationships. Br J Pharmacol 71:83-91.
    • (1980) Br J Pharmacol , vol.71 , pp. 83-91
    • Allen, K.E.1    Clark, E.R.2    Jordan, V.C.3
  • 2
    • 0344736918 scopus 로고    scopus 로고
    • Oxidative metabolism of tamoxifen to Z-4-hydroxy-tamoxifen by cytochrome P450 isoforms: An appraisal of in vitro studies
    • Coller JK (2003) Oxidative metabolism of tamoxifen to Z-4-hydroxy-tamoxifen by cytochrome P450 isoforms: an appraisal of in vitro studies. Clin Exp Pharmacol Physiol 30:845-848.
    • (2003) Clin Exp Pharmacol Physiol , vol.30 , pp. 845-848
    • Coller, J.K.1
  • 4
    • 0031031421 scopus 로고    scopus 로고
    • Variable contribution of cytochromes P450 2D6, 2C9 and 3A4 to the 4-hydroxylation of tamoxifen by human liver microsomes
    • Crewe HK, Ellis SW, Lennard MS, and Tucker GT (1997) Variable contribution of cytochromes P450 2D6, 2C9 and 3A4 to the 4-hydroxylation of tamoxifen by human liver microsomes. Biochem Pharmacol 53:171-178.
    • (1997) Biochem Pharmacol , vol.53 , pp. 171-178
    • Crewe, H.K.1    Ellis, S.W.2    Lennard, M.S.3    Tucker, G.T.4
  • 5
    • 0036325773 scopus 로고    scopus 로고
    • Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: Formation of the 4-hydroxy, 4′-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen
    • Crewe HK, Notley LM, Wunsch RM, Lennard MS, and Gillam EM (2002) Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4′-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos 30:869-874.
    • (2002) Drug Metab Dispos , vol.30 , pp. 869-874
    • Crewe, H.K.1    Notley, L.M.2    Wunsch, R.M.3    Lennard, M.S.4    Gillam, E.M.5
  • 7
    • 0030812209 scopus 로고    scopus 로고
    • CYP2D6 catalyzes tamoxifen 4-hydroxylation in human liver
    • Dehal SS and Kupfer D (1997) CYP2D6 catalyzes tamoxifen 4-hydroxylation in human liver. Cancer Res 57:3402-3406.
    • (1997) Cancer Res , vol.57 , pp. 3402-3406
    • Dehal, S.S.1    Kupfer, D.2
  • 8
    • 4243063941 scopus 로고    scopus 로고
    • Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: Prominent roles for CYP3A and CYP2D6
    • Desta Z, Ward BA, Soukhova NV, and Flockhart DA (2004) Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther 310:1062-1075.
    • (2004) J Pharmacol Exp Ther , vol.310 , pp. 1062-1075
    • Desta, Z.1    Ward, B.A.2    Soukhova, N.V.3    Flockhart, D.A.4
  • 9
    • 0032537396 scopus 로고    scopus 로고
    • Tamoxifen for early breast cancer: An overview of the randomised trials
    • Early Breast Cancer Trialists' Collaborative Group
    • Early Breast Cancer Trialists' Collaborative Group (1998) Tamoxifen for early breast cancer: an overview of the randomised trials. Lancet 351:1451-1467.
    • (1998) Lancet , vol.351 , pp. 1451-1467
  • 10
    • 0842301047 scopus 로고    scopus 로고
    • Correlation between the UDP- glucuronosyltransferase (UGT1A1) TATAA box polymorphism and carcinogen detoxification phenotype: Significantly decreased glucuronidating activity against benzo(a)pyrene-7,8-dihydrodiol(-) in liver microsomes from subjects with the UGT1A1*28 variant
    • Fang JL and Lazarus P (2004) Correlation between the UDP- glucuronosyltransferase (UGT1A1) TATAA box polymorphism and carcinogen detoxification phenotype: significantly decreased glucuronidating activity against benzo(a)pyrene-7,8-dihydrodiol(-) in liver microsomes from subjects with the UGT1A1*28 variant. Cancer Epidemiol Biomarkers Prev 13:102-109.
    • (2004) Cancer Epidemiol Biomarkers Prev , vol.13 , pp. 102-109
    • Fang, J.L.1    Lazarus, P.2
  • 12
    • 0021618186 scopus 로고
    • The pharmacology and clinical uses of tamoxifen
    • Furr BJ and Jordan VC (1984) The pharmacology and clinical uses of tamoxifen. Pharmacol Ther 25:127-205.
    • (1984) Pharmacol Ther , vol.25 , pp. 127-205
    • Furr, B.J.1    Jordan, V.C.2
  • 13
    • 0042827285 scopus 로고    scopus 로고
    • New approaches to the endocrine prevention and treatment of breast cancer
    • Howell A, Howell SJ, and Evans DG (2003) New approaches to the endocrine prevention and treatment of breast cancer. Cancer Chemother Pharmacol 52 (Suppl 1:)S39-S44.
    • (2003) Cancer Chemother Pharmacol , vol.52 , Issue.SUPPL. 1
    • Howell, A.1    Howell, S.J.2    Evans, D.G.3
  • 14
    • 0037329175 scopus 로고    scopus 로고
    • CYP2D6-mediated catalysis of tamoxifen aromatic hydroxylation with an NIH shift: Similar hydroxylation mechanism in chicken, rat and human liver microsomes
    • Hu Y, Dehal SS, Hynd G, Jones GB, and Kupfer D (2003) CYP2D6-mediated catalysis of tamoxifen aromatic hydroxylation with an NIH shift: similar hydroxylation mechanism in chicken, rat and human liver microsomes. Xenobiotica 33:141-151.
    • (2003) Xenobiotica , vol.33 , pp. 141-151
    • Hu, Y.1    Dehal, S.S.2    Hynd, G.3    Jones, G.B.4    Kupfer, D.5
  • 17
    • 0017665570 scopus 로고
    • A monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity
    • Jordan VC, Collins MM, Rowsby L, and Prestwich G (1977) A monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity. J Endocrinol 75:305-316.
    • (1977) J Endocrinol , vol.75 , pp. 305-316
    • Jordan, V.C.1    Collins, M.M.2    Rowsby, L.3    Prestwich, G.4
  • 18
    • 0019443284 scopus 로고
    • Geometric isomers of substituted triphenylethylenes and antiestrogen action
    • Jordan VC, Haldemann B, and Allen KE (1981) Geometric isomers of substituted triphenylethylenes and antiestrogen action. Endocrinology 108:1353-1361.
    • (1981) Endocrinology , vol.108 , pp. 1353-1361
    • Jordan, V.C.1    Haldemann, B.2    Allen, K.E.3
  • 19
    • 0021348096 scopus 로고
    • Bioactivities, estrogen receptor interactions, and plasminogen activator-inducing activities of tamoxifen and hydroxy-tamoxifen isomers in MCF-7 human breast cancer cells
    • Katzenellenbogen BS, Norman MJ, Eckert RL, Peltz SW, and Mangel WF (1984) Bioactivities, estrogen receptor interactions, and plasminogen activator-inducing activities of tamoxifen and hydroxy-tamoxifen isomers in MCF-7 human breast cancer cells. Cancer Res 44:112-119.
    • (1984) Cancer Res , vol.44 , pp. 112-119
    • Katzenellenbogen, B.S.1    Norman, M.J.2    Eckert, R.L.3    Peltz, S.W.4    Mangel, W.F.5
  • 20
    • 0038697813 scopus 로고    scopus 로고
    • Quantification of tamoxifen and three metabolites in plasma by high-performance liquid chromatography with fluorescence detection: Application to a clinical trial
    • Lee KH, Ward BA, Desta Z, Flockhart DA, and Jones DR (2003) Quantification of tamoxifen and three metabolites in plasma by high-performance liquid chromatography with fluorescence detection: application to a clinical trial. J Chromatogr B Analyt Technol Biomed Life Sci 791:245-253.
    • (2003) J Chromatogr B Analyt Technol Biomed Life Sci , vol.791 , pp. 245-253
    • Lee, K.H.1    Ward, B.A.2    Desta, Z.3    Flockhart, D.A.4    Jones, D.R.5
  • 21
    • 0020587401 scopus 로고
    • An estrogen receptor model to describe the regulation of prolactin synthesis by antiestrogens in vitro
    • Lieberman ME, Gorski J, and Jordan VC (1983) An estrogen receptor model to describe the regulation of prolactin synthesis by antiestrogens in vitro. J Biol Chem 258:4741-4745.
    • (1983) J Biol Chem , vol.258 , pp. 4741-4745
    • Lieberman, M.E.1    Gorski, J.2    Jordan, V.C.3
  • 22
    • 0023922814 scopus 로고
    • Identification of 4-hydroxy-N-desmethyltamoxifen as a metabolite of tamoxifen in human bile
    • Lien EA, Solheim E, Kvinnsland S, and Ueland PM (1988) Identification of 4-hydroxy-N-desmethyltamoxifen as a metabolite of tamoxifen in human bile. Cancer Res 48:2304-2308.
    • (1988) Cancer Res , vol.48 , pp. 2304-2308
    • Lien, E.A.1    Solheim, E.2    Kvinnsland, S.3    Ueland, P.M.4
  • 23
    • 0024584001 scopus 로고
    • Distribution of 4-hydroxy-N-desmethyltamoxifen and other tamoxifen metabolites in human biological fluids during tamoxifen treatment
    • Lien EA, Solheim E, Lea OA, Lundgren S, Kvinnsland S, and Ueland PM (1989) Distribution of 4-hydroxy-N-desmethyltamoxifen and other tamoxifen metabolites in human biological fluids during tamoxifen treatment. Cancer Res 49:2175-2183.
    • (1989) Cancer Res , vol.49 , pp. 2175-2183
    • Lien, E.A.1    Solheim, E.2    Lea, O.A.3    Lundgren, S.4    Kvinnsland, S.5    Ueland, P.M.6
  • 24
    • 17644387537 scopus 로고    scopus 로고
    • Endoxifen (4-hydroxy-N-desmethyltamoxifen) has anti-estrogenic effects in breast cancer cells with potency similar to 4-hydroxytamoxifen
    • Lim YC, Desta Z, Flockhart DA, and Skaar TC (2005) Endoxifen (4-hydroxy-N-desmethyltamoxifen) has anti-estrogenic effects in breast cancer cells with potency similar to 4-hydroxytamoxifen. Cancer Chemother Pharmacol 55:471-478.
    • (2005) Cancer Chemother Pharmacol , vol.55 , pp. 471-478
    • Lim, Y.C.1    Desta, Z.2    Flockhart, D.A.3    Skaar, T.C.4
  • 25
    • 0025833585 scopus 로고
    • Fatal myocardial infarction in the Scottish adjuvant tamoxifen trial; The Scottish Breast Cancer Committee
    • McDonald CC and Stewart HJ (1991) Fatal myocardial infarction in the Scottish adjuvant tamoxifen trial; The Scottish Breast Cancer Committee. BMJ 303:435-437.
    • (1991) BMJ , vol.303 , pp. 435-437
    • McDonald, C.C.1    Stewart, H.J.2
  • 26
    • 0025200665 scopus 로고
    • Structure-function relationships of hydroxylated metabolites of tamoxifen that control the proliferation of estrogen-responsive T47D breast cancer cells in vitro
    • Murphy CS, Langan-Fahey SM, McCague R, and Jordan VC (1990) Structure-function relationships of hydroxylated metabolites of tamoxifen that control the proliferation of estrogen-responsive T47D breast cancer cells in vitro. Mol Pharmacol 38:737-743.
    • (1990) Mol Pharmacol , vol.38 , pp. 737-743
    • Murphy, C.S.1    Langan-Fahey, S.M.2    McCague, R.3    Jordan, V.C.4
  • 28
    • 0032569831 scopus 로고    scopus 로고
    • Tamoxifen in the treatment of breast cancer
    • Osborne CK (1998) Tamoxifen in the treatment of breast cancer. N Engl J Med 339:1609-1618.
    • (1998) N Engl J Med , vol.339 , pp. 1609-1618
    • Osborne, C.K.1
  • 30
    • 0028898873 scopus 로고
    • Adjuvant tamoxifen therapy for early stage breast cancer and second primary malignancies: Stockholm Breast Cancer Study Group
    • Rutqvist LE, Johansson H, Signomklao T, Johansson U, Fornander T, and Wilking N (1995) Adjuvant tamoxifen therapy for early stage breast cancer and second primary malignancies: Stockholm Breast Cancer Study Group. J Natl Cancer Inst 87:645-651.
    • (1995) J Natl Cancer Inst , vol.87 , pp. 645-651
    • Rutqvist, L.E.1    Johansson, H.2    Signomklao, T.3    Johansson, U.4    Fornander, T.5    Wilking, N.6
  • 31
    • 0027325734 scopus 로고
    • Cardiac and thromboembolic morbidity among postmenopausal women with early-stage breast cancer in a randomized trial of adjuvant tamoxifen: The Stockholm Breast Cancer Study Group
    • Rutqvist LE and Mattsson A (1993) Cardiac and thromboembolic morbidity among postmenopausal women with early-stage breast cancer in a randomized trial of adjuvant tamoxifen: the Stockholm Breast Cancer Study Group. J Natl Cancer Inst 85:1398-1406.
    • (1993) J Natl Cancer Inst , vol.85 , pp. 1398-1406
    • Rutqvist, L.E.1    Mattsson, A.2
  • 32
    • 0346602691 scopus 로고    scopus 로고
    • Active tamoxifen metabolite plasma concentrations after coadministration of tamoxifen and the selective serotonin reuptake inhibitor paroxetine
    • Stearns V, Johnson MD, Rae JM, Morocho A, Novielli A, Bhargava P, Hayes DF, Desta Z, and Flockhart DA (2003) Active tamoxifen metabolite plasma concentrations after coadministration of tamoxifen and the selective serotonin reuptake inhibitor paroxetine. J Natl Cancer Inst 95:1758-1764.
    • (2003) J Natl Cancer Inst , vol.95 , pp. 1758-1764
    • Stearns, V.1    Johnson, M.D.2    Rae, J.M.3    Morocho, A.4    Novielli, A.5    Bhargava, P.6    Hayes, D.F.7    Desta, Z.8    Flockhart, D.A.9
  • 33
    • 33748318005 scopus 로고    scopus 로고
    • Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants
    • Sun D, Chen G, Dellinger RW, Duncan K, Fang JL, and Lazarus P (2006) Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants. Breast Cancer Res 8:R50.
    • (2006) Breast Cancer Res , vol.8
    • Sun, D.1    Chen, G.2    Dellinger, R.W.3    Duncan, K.4    Fang, J.L.5    Lazarus, P.6
  • 36
    • 1642457368 scopus 로고    scopus 로고
    • Characterization of N-glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human liver: Importance of UDP-glucuronosyltransferase 1A4
    • Wiener D, Doerge DR, Fang JL, Upadhyaya P, and Lazarus P (2004a) Characterization of N-glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human liver: importance of UDP-glucuronosyltransferase 1A4. Drug Metab Dispos 32:72-79.
    • (2004) Drug Metab Dispos , vol.32 , pp. 72-79
    • Wiener, D.1    Doerge, D.R.2    Fang, J.L.3    Upadhyaya, P.4    Lazarus, P.5
  • 37
    • 0842325733 scopus 로고    scopus 로고
    • Correlation between UDPglucuronosyltransferase genotypes and 4-(methylnitrosamino)-1-(3-pyridyl)-1- butanone glucuronidation phenotype in human liver microsomes
    • Wiener D, Fang JL, Dossett N, and Lazarus P (2004b) Correlation between UDPglucuronosyltransferase genotypes and 4-(methylnitrosamino)-1-(3-pyridyl)-1- butanone glucuronidation phenotype in human liver microsomes. Cancer Res 64:1190-1196.
    • (2004) Cancer Res , vol.64 , pp. 1190-1196
    • Wiener, D.1    Fang, J.L.2    Dossett, N.3    Lazarus, P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.