{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T00:38:29Z","timestamp":1760747909971,"version":"build-2065373602"},"reference-count":37,"publisher":"Elsevier BV","issue":"3","license":[{"start":{"date-parts":[[2010,2,1]],"date-time":"2010-02-01T00:00:00Z","timestamp":1264982400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2010,2,1]],"date-time":"2010-02-01T00:00:00Z","timestamp":1264982400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["The Journal of Steroid Biochemistry and Molecular Biology"],"published-print":{"date-parts":[[2010,2]]},"DOI":"10.1016\/j.jsbmb.2009.11.008","type":"journal-article","created":{"date-parts":[[2009,11,25]],"date-time":"2009-11-25T08:30:47Z","timestamp":1259137847000},"page":"151-161","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":9,"title":["Mechanism of action of bolandiol (19-nortestosterone-3\u03b2,17\u03b2-diol), a unique anabolic steroid with androgenic, estrogenic, and progestational activities"],"prefix":"10.1016","volume":"118","author":[{"given":"Barbara J.","family":"Attardi","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Stephanie T.","family":"Page","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sheri A.","family":"Hild","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christopher C.","family":"Coss","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alvin M.","family":"Matsumoto","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"key":"10.1016\/j.jsbmb.2009.11.008_bib1","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1016\/j.drudis.2007.01.003","article-title":"Expanding the therapeutic use of androgens via selective androgen receptor modulators (SARMs)","volume":"12","author":"Gao","year":"2007","journal-title":"Drug Discov. Today"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib2","doi-asserted-by":"crossref","first-page":"1328","DOI":"10.1124\/dmd.106.010165","article-title":"Quantitative determination of metabolic products of 19-norandrostenediol in human plasma using gas chromatography\/mass spectrometry","volume":"34","author":"Schrader","year":"2006","journal-title":"Drug Metab. Dispos."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib3","doi-asserted-by":"crossref","first-page":"1987","DOI":"10.1210\/en.2007-0956","article-title":"Tissue selectivity of the anabolic steroid, 19-nor-4-androstenediol-3beta,17beta-diol in male Sprague Dawley rats: selective stimulation of muscle mass and bone mineral density relative to prostate mass","volume":"149","author":"Page","year":"2008","journal-title":"Endocrinology"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib4","doi-asserted-by":"crossref","first-page":"426","DOI":"10.1007\/s004210100395","article-title":"The effects of supplementation with 19-nor-4-androstene-3, 17-dione and 19-nor-4-androstene-3,17-diol on body composition and athletic performance in previously weight-trained male athletes","volume":"84","author":"Van Gammeren","year":"2001","journal-title":"Eur. J. Appl. Physiol."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib5","doi-asserted-by":"crossref","first-page":"734","DOI":"10.1016\/S0899-9007(02)00834-1","article-title":"Effects of norandrostenedione and norandrostenediol in resistance-trained men","volume":"18","author":"Van Gammeren","year":"2002","journal-title":"Nutrition"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib6","doi-asserted-by":"crossref","first-page":"684","DOI":"10.1016\/j.steroids.2009.02.012","article-title":"In vivo MRI evaluation of anabolic steroid precursor growth effects in a guinea pig model","volume":"74","author":"Tang","year":"2009","journal-title":"Steroids"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib7","doi-asserted-by":"crossref","first-page":"413","DOI":"10.1055\/s-2007-1024704","article-title":"Influence of anabolic steroids on body composition, blood pressure, lipid profile and liver functions in body builders","volume":"12","author":"Kuipers","year":"1991","journal-title":"Int. J. Sports Med."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib8","doi-asserted-by":"crossref","first-page":"3167","DOI":"10.1210\/jc.2002-021827","article-title":"Randomized placebo-controlled trial of androgen effects on muscle and bone in men requiring long-term systemic glucocorticoid treatment","volume":"88","author":"Crawford","year":"2003","journal-title":"J. Clin. Endocrinol. Metab."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib9","doi-asserted-by":"crossref","first-page":"648","DOI":"10.1093\/gerona\/60.5.648","article-title":"The effect of nandrolone decanoate on bone mineral density, muscle mass, and hemoglobin levels in elderly women with osteoporosis: a double-blind, randomized, placebo-controlled clinical trial","volume":"60","author":"Frisoli","year":"2005","journal-title":"J. Gerontol. A: Biol. Sci. Med. Sci."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib10","first-page":"144","article-title":"The metabolism of orally ingested 19-nor-4-androstene-3,17-dione and 19-nor-4-androstene-3,17-diol in healthy, resistance-trained men","volume":"15","author":"Colker","year":"2001","journal-title":"J. Strength Cond. Res."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib11","doi-asserted-by":"crossref","first-page":"124","DOI":"10.1093\/jat\/29.2.124","article-title":"Quantification and profiling of 19-norandrosterone and 19-noretiocholanolone in human urine after consumption of a nutritional supplement and norsteroids","volume":"29","author":"Tseng","year":"2005","journal-title":"J. Anal. Toxicol."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib12","doi-asserted-by":"crossref","first-page":"817","DOI":"10.1016\/j.steroids.2006.05.012","article-title":"Detection and quantification of glucuro- and sulfoconjugated metabolites in human urine following oral administration of xenobiotic 19-norsteroids","volume":"71","author":"Tseng","year":"2006","journal-title":"Steroids"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib13","doi-asserted-by":"crossref","first-page":"198","DOI":"10.1016\/j.toxlet.2008.01.014","article-title":"The prohormone 19-norandrostenedione displays selective androgen receptor modulator (SARM) like properties after subcutaneous administration","volume":"177","author":"Diel","year":"2008","journal-title":"Toxicol. Lett."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib14","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1016\/S0303-7207(01)00743-2","article-title":"CDB-4124 and its putative monodemethylated metabolite, CDB-4453, are potent antiprogestins with reduced antiglucocorticoid activity: in vitro comparison to mifepristone and CDB-2914","volume":"188","author":"Attardi","year":"2002","journal-title":"Mol. Cell. Endocrinol."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib15","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/j.mce.2004.04.013","article-title":"Steroid hormonal regulation of growth, prostate specific antigen secretion, and transcription mediated by the mutated androgen receptor in CWR22Rv1 human prostate carcinoma cells","volume":"222","author":"Attardi","year":"2004","journal-title":"Mol. Cell. Endocrinol."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib16","doi-asserted-by":"crossref","first-page":"214","DOI":"10.1016\/j.jsbmb.2007.11.009","article-title":"Dimethandrolone (7alpha, 11beta-dimethyl-19-nortestosterone) and 11beta-methyl-19-nortestosterone are not converted to aromatic A-ring products in the presence of recombinant human aromatase","volume":"110","author":"Attardi","year":"2008","journal-title":"J. Steroid Biochem. Mol. Biol."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib17","doi-asserted-by":"crossref","first-page":"20870","DOI":"10.1016\/S0021-9258(19)36867-X","article-title":"Modulation by vitamin B6 of glucocorticoid receptor-mediated gene expression requires transcription factors in addition to the glucocorticoid receptor","volume":"268","author":"Allgood","year":"1993","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib18","doi-asserted-by":"crossref","first-page":"633","DOI":"10.1016\/0092-8674(82)90218-5","article-title":"Variant T47D human breast cancer cells with high progesterone-receptor levels despite estrogen and antiestrogen resistance","volume":"28","author":"Horwitz","year":"1982","journal-title":"Cell"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib19","doi-asserted-by":"crossref","first-page":"175","DOI":"10.3181\/00379727-83-20301","article-title":"Myotrophic activity of 19-nortestosterone and other steroids determined by modified levator ani muscle method","volume":"83","author":"Hershberger","year":"1953","journal-title":"Proc. Soc. Exp. Biol. Med."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib20","doi-asserted-by":"crossref","first-page":"3016","DOI":"10.1210\/en.2005-1524","article-title":"Dimethandrolone undecanoate: a new potent orally active androgen with progestational activity","volume":"147","author":"Attardi","year":"2006","journal-title":"Endocrinology"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib21","series-title":"Program of the 89th Annual Meeting of The Endocrine Society","article-title":"Dimethandrolone (7\u03b1,11\u03b2-dimethyl-19-nortestosterone) does not require 5\u03b1-reduction to exert its maximal biological effects","author":"Attardi","year":"2007"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib22","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1210\/endo-19-1-33","article-title":"The nature of the estrogenic substance in human male urine and bull testis","volume":"19","author":"Dorfman","year":"1936","journal-title":"Endocrinology"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib23","doi-asserted-by":"crossref","first-page":"747","DOI":"10.1210\/endo-28-5-747","article-title":"The mouse uterine weight method for the assay of estrogens","volume":"28","author":"Evans","year":"1941","journal-title":"Endocrinology"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib24","doi-asserted-by":"crossref","first-page":"288","DOI":"10.1006\/faat.1996.0198","article-title":"Survey and assessment of mammalian estrogen biological assays for hazard characterization","volume":"34","author":"Reel","year":"1996","journal-title":"Fundam. Appl. Toxicol."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib25","doi-asserted-by":"crossref","first-page":"465","DOI":"10.1210\/er.2007-0041","article-title":"Advances in male contraception","volume":"29","author":"Page","year":"2008","journal-title":"Endocrinol. Rev."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib26","doi-asserted-by":"crossref","first-page":"385","DOI":"10.1210\/en.2008-0674","article-title":"Preclinical characterization of a (S)-N-(4-cyano-3-trifluoromethyl-phenyl)-3-(3-fluoro, 4-chlorophenoxy)-2-hydroxy-2-methyl-propanamide: a selective androgen receptor modulator for hormonal male contraception","volume":"150","author":"Jones","year":"2009","journal-title":"Endocrinology"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib27","doi-asserted-by":"crossref","first-page":"4509","DOI":"10.1210\/endo.140.10.7039","article-title":"Androgen-induced regrowth in the castrated rat ventral prostate: role of 5alpha-reductase","volume":"140","author":"Wright","year":"1999","journal-title":"Endocrinology"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib28","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1124\/mi.7.1.3","article-title":"Ockham's razor and selective androgen receptor modulators (SARMS): are we overlooking the role of 5alpha-reductase?","volume":"7","author":"Gao","year":"2007","journal-title":"Mol. Interv."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib29","doi-asserted-by":"crossref","first-page":"424","DOI":"10.1210\/endo.139.1.5809","article-title":"Rat estrogen receptor-alpha and -beta, and progesterone receptor mRNA expression in various prostatic lobes and microdissected normal and dysplastic epithelial tissues of the Noble rats","volume":"139","author":"Lau","year":"1998","journal-title":"Endocrinology"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib30","doi-asserted-by":"crossref","first-page":"1106","DOI":"10.1210\/me.2003-0032","article-title":"Selective modulation of genomic and nongenomic androgen responses by androgen receptor ligands","volume":"17","author":"Lutz","year":"2003","journal-title":"Mol. Endocrinol."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib31","doi-asserted-by":"crossref","first-page":"2448","DOI":"10.1210\/me.2008-0160","article-title":"Steroidal androgens and nonsteroidal, tissue selective androgen receptor modulator (SARM), S-22, regulate androgen receptor function through distinct genomic and nongenomic signaling pathways","volume":"22","author":"Narayanan","year":"2008","journal-title":"Mol. Endocrinol."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib32","doi-asserted-by":"crossref","first-page":"3586","DOI":"10.1210\/en.2002-0164","article-title":"Testosterone stimulates intracellular calcium release and mitogen-activated protein kinases via a G protein-coupled receptor in skeletal muscle cells","volume":"144","author":"Estrada","year":"2003","journal-title":"Endocrinology"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib33","doi-asserted-by":"crossref","first-page":"1386","DOI":"10.1210\/en.2005-1139","article-title":"Testosterone induces an intracellular calcium increase by a nongenomic mechanism in cultured rat cardiac myocytes","volume":"147","author":"Vincencio","year":"2006","journal-title":"Endocrinology"},{"key":"10.1016\/j.jsbmb.2009.11.008_bib34","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1210\/er.2003-0023","article-title":"Coregulator function: a key to understanding tissue specificity of selective receptor modulators","volume":"1","author":"Smith","year":"2004","journal-title":"Endocrinol. Rev."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib35","doi-asserted-by":"crossref","first-page":"452","DOI":"10.1016\/j.chembiol.2009.01.016","article-title":"Differential presentation of protein interaction surfaces on the androgen receptor defines the pharmacological actions of bound ligands","volume":"16","author":"Norris","year":"2009","journal-title":"Chem. Biol."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib36","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1016\/S0303-7207(97)00168-8","article-title":"Steroid-independent activation of androgen receptor in androgen-independent prostate cancer. A possible role for the MAP kinase signal transduction pathway?","volume":"134","author":"Zhu","year":"1997","journal-title":"Mol. Cell. Endocrinol."},{"key":"10.1016\/j.jsbmb.2009.11.008_bib37","doi-asserted-by":"crossref","first-page":"503","DOI":"10.1210\/me.2005-0351","article-title":"Stress kinase signaling regulates androgen receptor phosphorylation, transcription, and localization","volume":"20","author":"Gioeli","year":"2006","journal-title":"Mol. Endocrinol."}],"container-title":["The Journal of Steroid Biochemistry and Molecular Biology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960076009002799?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960076009002799?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,17]],"date-time":"2025-10-17T23:33:31Z","timestamp":1760744011000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0960076009002799"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,2]]},"references-count":37,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2010,2]]}},"alternative-id":["S0960076009002799"],"URL":"https:\/\/doi.org\/10.1016\/j.jsbmb.2009.11.008","relation":{},"ISSN":["0960-0760"],"issn-type":[{"type":"print","value":"0960-0760"}],"subject":[],"published":{"date-parts":[[2010,2]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Mechanism of action of bolandiol (19-nortestosterone-3\u03b2,17\u03b2-diol), a unique anabolic steroid with androgenic, estrogenic, and progestational activities","name":"articletitle","label":"Article Title"},{"value":"The Journal of Steroid Biochemistry and Molecular Biology","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.jsbmb.2009.11.008","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"Copyright \u00a9 2009 Elsevier Ltd. Published by Elsevier Ltd. All rights reserved.","name":"copyright","label":"Copyright"}]}}