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Volumn 110, Issue 3-5, 2008, Pages 214-222

Dimethandrolone (7α,11β-dimethyl-19-nortestosterone) and 11β-methyl-19-nortestosterone are not converted to aromatic A-ring products in the presence of recombinant human aromatase

Author keywords

19 Norandrogens; C19 androgens; Estrogen receptors; Hormonal therapy for men; Human aromatase; Transcription

Indexed keywords

11BETA METHYL 19 NORTESTOSTERONE; 11BETA METHYLESTRADIOL; 16ALPHA HYDROXYANDROSTENEDIONE; 16ALPHA HYDROXYESTRONE; 17 METHYLESTRADIOL; 17ALPHA METHYTESTOSTERONE; 19 NORPROGESTIN; 19 NORSTEROID; 7ALPHA METHYLESTRADIOL; 7ALPHA,11BETA DIMETHYLESTRADIOL; ACETONITRILE; ANDROGEN; ANDROSTENEDIONE; AROMATASE; CDB 1321; DIMETHANDROLONE; ESTRADIOL; ESTROGEN; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; ESTRONE; ETHINYLESTRADIOL; LETROZOLE; NANDROLONE; NANDROLONE DERIVATIVE; NORETHISTERONE; PROGESTERONE DERIVATIVE; TESTOSTERONE; TRESTOLONE; 11 METHYL 19 NORTESTOSTERONE; 11-METHYL-19-NORTESTOSTERONE; 7ALPHA,11BETA DIMETHYL 19 NORTESTOSTERONE; 7ALPHA,11BETA-DIMETHYL-19-NORTESTOSTERONE; DRUG DERIVATIVE; ESTRANE DERIVATIVE; METHYLESTRENOLONE; RECOMBINANT PROTEIN;

EID: 44849091208     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2007.11.009     Document Type: Article
Times cited : (35)

References (42)
  • 1
    • 0041311217 scopus 로고    scopus 로고
    • Testosterone replacement therapy in male hypogonadism
    • Byrne M.M., and Nieschlag E. Testosterone replacement therapy in male hypogonadism. J. Endocrinol. Invest. 26 (2003) 481-489
    • (2003) J. Endocrinol. Invest. , vol.26 , pp. 481-489
    • Byrne, M.M.1    Nieschlag, E.2
  • 2
    • 1542284265 scopus 로고    scopus 로고
    • The endocrine pharmacology of testosterone therapy in men
    • Oettel M. The endocrine pharmacology of testosterone therapy in men. Naturwissenschaften 91 (2004) 66-76
    • (2004) Naturwissenschaften , vol.91 , pp. 66-76
    • Oettel, M.1
  • 3
    • 33646809681 scopus 로고    scopus 로고
    • Dimethandrolone undecanoate: a new potent orally active androgen with progestational activity
    • Attardi B.J., Hild S.A., and Reel J.R. Dimethandrolone undecanoate: a new potent orally active androgen with progestational activity. Endocrinology 147 (2006) 3016-3026
    • (2006) Endocrinology , vol.147 , pp. 3016-3026
    • Attardi, B.J.1    Hild, S.A.2    Reel, J.R.3
  • 5
    • 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 M.E., Oppers-Tiemissen H.M., Leysen D., Verheul H.A.M., and Kloosterboer H.J. 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 68 (2003) 235-243
    • (2003) Steroids , vol.68 , pp. 235-243
    • de Gooyer, M.E.1    Oppers-Tiemissen, H.M.2    Leysen, D.3    Verheul, H.A.M.4    Kloosterboer, H.J.5
  • 6
    • 33846619697 scopus 로고    scopus 로고
    • Molecular basis for the aromatization reaction and exemestane-mediated irreversible inhibition of human aromatase
    • Hong Y., Yu B., Sherman M., Yuan Y.-C., Zhou D., and Chen S. Molecular basis for the aromatization reaction and exemestane-mediated irreversible inhibition of human aromatase. Mol. Endocrinol. 21 (2007) 401-414
    • (2007) Mol. Endocrinol. , vol.21 , pp. 401-414
    • Hong, Y.1    Yu, B.2    Sherman, M.3    Yuan, Y.-C.4    Zhou, D.5    Chen, S.6
  • 7
    • 0022492858 scopus 로고
    • Purification and reconstitution of human placental aromatase A cytochrome P-450-type monooxygenase
    • Tan L., and Muto N. Purification and reconstitution of human placental aromatase A cytochrome P-450-type monooxygenase. Eur. J. Biochem. 156 (1986) 243-250
    • (1986) Eur. J. Biochem. , vol.156 , pp. 243-250
    • Tan, L.1    Muto, N.2
  • 8
    • 0023868560 scopus 로고
    • Aromatization of testosterone and 19-nortestosterone by a single enzyme from equine testicular microsomes: differences from human placental microsomes
    • Silberzahn P., Gaillard J.L., Quincey D., Dintinger T., and Al-Timimi I. Aromatization of testosterone and 19-nortestosterone by a single enzyme from equine testicular microsomes: differences from human placental microsomes. J. Steroid Biochem. 29 (1988) 119-125
    • (1988) J. Steroid Biochem. , vol.29 , pp. 119-125
    • Silberzahn, P.1    Gaillard, J.L.2    Quincey, D.3    Dintinger, T.4    Al-Timimi, I.5
  • 11
    • 0023729658 scopus 로고
    • Formation and metabolism of 5(10)-estrene-3 beta, 17 beta-diol, a novel 19-norandrogen produced by porcine granulosa cells from C19 aromatizable androgens
    • Khalil M.W., Chung N., Morley P., Glasier M.A., and Armstrong D.T. Formation and metabolism of 5(10)-estrene-3 beta, 17 beta-diol, a novel 19-norandrogen produced by porcine granulosa cells from C19 aromatizable androgens. Biochem. Biophys. Res. Commun. 155 (1988) 144-150
    • (1988) Biochem. Biophys. Res. Commun. , vol.155 , pp. 144-150
    • Khalil, M.W.1    Chung, N.2    Morley, P.3    Glasier, M.A.4    Armstrong, D.T.5
  • 12
  • 13
    • 0028175348 scopus 로고
    • Aromatization of 7-alpha-methyl-19-nortestosterone by human placental microsomes in vitro
    • LaMorte A., Kumar N., Bardin C.W., and Sundaram K. Aromatization of 7-alpha-methyl-19-nortestosterone by human placental microsomes in vitro. J. Steroid Biochem. Mol. Biol. 48 (1994) 297-304
    • (1994) J. Steroid Biochem. Mol. Biol. , vol.48 , pp. 297-304
    • LaMorte, A.1    Kumar, N.2    Bardin, C.W.3    Sundaram, K.4
  • 14
    • 0029068573 scopus 로고
    • Different patterns of metabolism determine the relative anabolic activity of 19-norandrogens
    • Sundaram K., Kumar N., Monder C., and Bardin C.W. Different patterns of metabolism determine the relative anabolic activity of 19-norandrogens. J. Steroid Biochem. Mol. Biol. 53 (1995) 253-257
    • (1995) J. Steroid Biochem. Mol. Biol. , vol.53 , pp. 253-257
    • Sundaram, K.1    Kumar, N.2    Monder, C.3    Bardin, C.W.4
  • 15
    • 2142701431 scopus 로고    scopus 로고
    • In vitro antiprogestational/antiglucocorticoid activity and progestin and glucocorticoid receptor binding of the putative metabolites and synthetic derivatives of CDB-2914, CDB-4124, and mifepristone
    • Attardi B.J., Burgenson J., Hild S.A., and Reel J.R. In vitro antiprogestational/antiglucocorticoid activity and progestin and glucocorticoid receptor binding of the putative metabolites and synthetic derivatives of CDB-2914, CDB-4124, and mifepristone. J. Steroid Biochem. Mol. Biol. 88 (2004) 277-288
    • (2004) J. Steroid Biochem. Mol. Biol. , vol.88 , pp. 277-288
    • Attardi, B.J.1    Burgenson, J.2    Hild, S.A.3    Reel, J.R.4
  • 16
    • 33646787774 scopus 로고    scopus 로고
    • Lack of aromatisation of the 3-keto-4-ene metabolite of tibolone to an estrogenic derivative
    • Raobaikady B., Parsons M.F.C., Reed M.J., and Purohit A. Lack of aromatisation of the 3-keto-4-ene metabolite of tibolone to an estrogenic derivative. Steroids 71 (2006) 639-646
    • (2006) Steroids , vol.71 , pp. 639-646
    • Raobaikady, B.1    Parsons, M.F.C.2    Reed, M.J.3    Purohit, A.4
  • 17
    • 0035544730 scopus 로고    scopus 로고
    • 17α-Methyl testosterone is a competitive inhibitor of aromatase activity in Jar choriocarcinoma cells and macrophage-like THP-1 cells in culture
    • Mor G., Eliza M., Song J., Wiita B., Chen S., and Naftolin F. 17α-Methyl testosterone is a competitive inhibitor of aromatase activity in Jar choriocarcinoma cells and macrophage-like THP-1 cells in culture. J. Steroid Biochem. Mol. Biol. 79 (2001) 239-246
    • (2001) J. Steroid Biochem. Mol. Biol. , vol.79 , pp. 239-246
    • Mor, G.1    Eliza, M.2    Song, J.3    Wiita, B.4    Chen, S.5    Naftolin, F.6
  • 18
    • 0019449456 scopus 로고
    • Enzyme-generated intermediates derived from 4-androstene-3,6,17-trione and 1,4,6-androstatriene-3,17-dione cause a time-dependent decrease in human placental aromatase activity
    • Covey D.F., and Hood W.F. Enzyme-generated intermediates derived from 4-androstene-3,6,17-trione and 1,4,6-androstatriene-3,17-dione cause a time-dependent decrease in human placental aromatase activity. Endocrinology 108 (1981) 1597-1599
    • (1981) Endocrinology , vol.108 , pp. 1597-1599
    • Covey, D.F.1    Hood, W.F.2
  • 20
    • 33646178258 scopus 로고    scopus 로고
    • Synthetic 19-nortestosterone derivatives as estrogen receptor alpha subtype-selective ligands induce similar receptor conformational changes and steroid receptor coactivator recruitment than natural estrogens
    • Garcia-Becerra R., Borja-Cacho E., Cooney A.J., Smith C.L., Lemus A.E., Perez-Palacios G., and Larrea F. Synthetic 19-nortestosterone derivatives as estrogen receptor alpha subtype-selective ligands induce similar receptor conformational changes and steroid receptor coactivator recruitment than natural estrogens. J. Steroid Biochem. Mol. Biol. 99 (2006) 108-114
    • (2006) J. Steroid Biochem. Mol. Biol. , vol.99 , pp. 108-114
    • Garcia-Becerra, R.1    Borja-Cacho, E.2    Cooney, A.J.3    Smith, C.L.4    Lemus, A.E.5    Perez-Palacios, G.6    Larrea, F.7
  • 21
    • 33749990827 scopus 로고    scopus 로고
    • Enhanced formation of non-phenolic androgen metabolites with intrinsic oestrogen-like gene transactivation potency in human breast cancer cells: a distinctive metabolic pattern
    • Perez-Palacios G., Santillian R., Garcia-Becerra R., Borja-Cacho E., Larrea F., Damian-Matsumura P., Gonzalez L., and Lemus A.E. Enhanced formation of non-phenolic androgen metabolites with intrinsic oestrogen-like gene transactivation potency in human breast cancer cells: a distinctive metabolic pattern. J. Endocrinol. 190 (2006) 805-818
    • (2006) J. Endocrinol. , vol.190 , pp. 805-818
    • Perez-Palacios, G.1    Santillian, R.2    Garcia-Becerra, R.3    Borja-Cacho, E.4    Larrea, F.5    Damian-Matsumura, P.6    Gonzalez, L.7    Lemus, A.E.8
  • 23
    • 26844495001 scopus 로고    scopus 로고
    • Survey and assessment of mammalian estrogen biological assays for hazard characterization
    • Reel J.R., Lamb IV J.C., and Neal B.H. Survey and assessment of mammalian estrogen biological assays for hazard characterization. Fund. Appl. Toxicol. 34 (1996) 288-305
    • (1996) Fund. Appl. Toxicol. , vol.34 , pp. 288-305
    • Reel, J.R.1    Lamb IV, J.C.2    Neal, B.H.3
  • 24
    • 84964130498 scopus 로고
    • Myotrophic activity of 19-nortestosterone and other steroids determined by modified levator ani muscle method
    • Hershberger L.G., Shipley E.G., and Meyer R.K. Myotrophic activity of 19-nortestosterone and other steroids determined by modified levator ani muscle method. Proc. Soc. Exp. Biol. Med. 83 (1953) 175-180
    • (1953) Proc. Soc. Exp. Biol. Med. , vol.83 , pp. 175-180
    • Hershberger, L.G.1    Shipley, E.G.2    Meyer, R.K.3
  • 26
  • 29
    • 33646489631 scopus 로고    scopus 로고
    • Low estradiol levels linked to low-trauma hip fractures in men
    • Amin S. Low estradiol levels linked to low-trauma hip fractures in men. Am. J. Med. 119 (2006) 426-433
    • (2006) Am. J. Med. , vol.119 , pp. 426-433
    • Amin, S.1
  • 32
    • 33846914931 scopus 로고    scopus 로고
    • Height and bone mineral density in androgen insensitivity syndrome with mutations in the androgen receptor gene
    • Danilovic D.L., Correa P.H., Costa E.M., Melo K.F., Mendonca B.B., and Arnhold I.J. Height and bone mineral density in androgen insensitivity syndrome with mutations in the androgen receptor gene. Osteoporosis Int. 18 (2007) 369-374
    • (2007) Osteoporosis Int. , vol.18 , pp. 369-374
    • Danilovic, D.L.1    Correa, P.H.2    Costa, E.M.3    Melo, K.F.4    Mendonca, B.B.5    Arnhold, I.J.6
  • 33
    • 33747634595 scopus 로고    scopus 로고
    • Bone mineral density in the complete androgen insensitivity and 5alpha-reductase-2 deficiency syndromes
    • Sobel V., Schwartz B., Zhu Y.S., Cordero J.J., and Imperato-McGinley J. Bone mineral density in the complete androgen insensitivity and 5alpha-reductase-2 deficiency syndromes. J. Clin. Endocrinol. Metab. 91 (2006) 3017-3023
    • (2006) J. Clin. Endocrinol. Metab. , vol.91 , pp. 3017-3023
    • Sobel, V.1    Schwartz, B.2    Zhu, Y.S.3    Cordero, J.J.4    Imperato-McGinley, J.5
  • 35
    • 18044387619 scopus 로고    scopus 로고
    • Bone and muscle protective potential of the prostate-sparing synthetic androgen 7α-methyl-19-nortestosterone: evidence from the aged orchidectomized male rat model
    • Venken K., Boonen S., Van Herck E., Vandenput L., Kumar N., Sitruk-Ware R., Sundaram K., Bouillon R., and Vanderschueren D. Bone and muscle protective potential of the prostate-sparing synthetic androgen 7α-methyl-19-nortestosterone: evidence from the aged orchidectomized male rat model. Bone 36 (2005) 663-670
    • (2005) Bone , vol.36 , pp. 663-670
    • Venken, K.1    Boonen, S.2    Van Herck, E.3    Vandenput, L.4    Kumar, N.5    Sitruk-Ware, R.6    Sundaram, K.7    Bouillon, R.8    Vanderschueren, D.9
  • 37
    • 0031788043 scopus 로고    scopus 로고
    • Effects of castration and chronic steroid treatments on hypothalamic gonadotropin-releasing hormone content and pituitary gonadotropins in male wild-type and estrogen receptor-alpha knockout mice
    • Lindzey J., Wetsel W.C., Couse J.F., Stoker T., Cooper R., and Korach K.S. Effects of castration and chronic steroid treatments on hypothalamic gonadotropin-releasing hormone content and pituitary gonadotropins in male wild-type and estrogen receptor-alpha knockout mice. Endocrinology 139 (1998) 4092-4101
    • (1998) Endocrinology , vol.139 , pp. 4092-4101
    • Lindzey, J.1    Wetsel, W.C.2    Couse, J.F.3    Stoker, T.4    Cooper, R.5    Korach, K.S.6
  • 38
    • 0033400405 scopus 로고    scopus 로고
    • Steroid feedback on gonadotropin release and pituitary gonadotropin subunit mRNA in mice lacking a functional estrogen receptor alpha
    • Wersinger S.R., Haisenleder D.J., Lubahn D.B., and Rissman E.F. Steroid feedback on gonadotropin release and pituitary gonadotropin subunit mRNA in mice lacking a functional estrogen receptor alpha. Endocrine 11 (1999) 137-143
    • (1999) Endocrine , vol.11 , pp. 137-143
    • Wersinger, S.R.1    Haisenleder, D.J.2    Lubahn, D.B.3    Rissman, E.F.4
  • 39
    • 0344530475 scopus 로고    scopus 로고
    • Lack of functional estrogen receptor beta gene disrupts pubertal male sexual behavior
    • Temple J.L., Scordalakes E.M., Bodo C., Gustafsson J.A., and Rissman E.F. Lack of functional estrogen receptor beta gene disrupts pubertal male sexual behavior. Horm. Behav. 44 (2003) 427-434
    • (2003) Horm. Behav. , vol.44 , pp. 427-434
    • Temple, J.L.1    Scordalakes, E.M.2    Bodo, C.3    Gustafsson, J.A.4    Rissman, E.F.5
  • 40
    • 12344298592 scopus 로고    scopus 로고
    • Role of estrogens in development of prostate cancer
    • Harkonen P.L., and Makela S.I. Role of estrogens in development of prostate cancer. J. Steroid Biochem. Mol. Biol. 92 (2004) 297-302
    • (2004) J. Steroid Biochem. Mol. Biol. , vol.92 , pp. 297-302
    • Harkonen, P.L.1    Makela, S.I.2
  • 41
    • 34247104593 scopus 로고    scopus 로고
    • The role of estrogens in prostate carcinogenesis: a rationale for chemoprevention
    • Bosland M.C. The role of estrogens in prostate carcinogenesis: a rationale for chemoprevention. Rev. Urol. 7 (2005) S4-S10
    • (2005) Rev. Urol. , vol.7
    • Bosland, M.C.1
  • 42
    • 33749501951 scopus 로고    scopus 로고
    • Endogenous sex hormones, cognitive decline, and future dementia in old men
    • Geerlings M.I. Endogenous sex hormones, cognitive decline, and future dementia in old men. Ann. Neurol. 60 (2006) 346-355
    • (2006) Ann. Neurol. , vol.60 , pp. 346-355
    • Geerlings, M.I.1


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