5α-Androstane-3β,17β-diol

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5α-Androstane-3β,17β-diol
Androstanediol.png
Identifiers
PubChem 242332
ChemSpider 211834
ChEMBL CHEMBL316048
Jmol-3D images Image 1
Properties
Molecular formula C19H32O2
Molar mass 292.456 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

5α-Androstane-3β,17β-diol, also called 3β-androstanediol, and often shortened to 3β-diol, is an endogenous steroid hormone. It is a 5α-reduced and 17β-hydroxylated metabolite of dehydroepiandrosterone (DHEA) as well as a 3β-hydroxylated metabolite of dihydrotestosterone (DHT). Similarly to DHEA, 3β-diol is a high-affinity full agonist of the ERβ, and hence, an estrogen. In contrast, it does not bind to the androgen receptor.[1] As a result of activation of the ERβ, 3β-diol has antiproliferative effects against prostate cancer cells and proliferative effects on breast cancer cells.[2][3]

A determination of the circulating levels of 3β-diol in humans found concentrations of 239 ± 76 pg/ml and 82 ± 45 pg/ml of the compound in normal male and female serum, respectively.[4]

See also[edit]

References[edit]

  1. ^ Oliveira AG, Coelho PH, Guedes FD, Mahecha GA, Hess RA, Oliveira CA (December 2007). "5alpha-Androstane-3beta,17beta-diol (3beta-diol), an estrogenic metabolite of 5alpha-dihydrotestosterone, is a potent modulator of estrogen receptor ERbeta expression in the ventral prostrate of adult rats". Steroids 72 (14): 914–22. doi:10.1016/j.steroids.2007.08.001. PMID 17854852. 
  2. ^ Weihua Z, Lathe R, Warner M, Gustafsson JA (October 2002). "An endocrine pathway in the prostate, ERbeta, AR, 5alpha-androstane-3beta,17beta-diol, and CYP7B1, regulates prostate growth". Proceedings of the National Academy of Sciences of the United States of America 99 (21): 13589–94. doi:10.1073/pnas.162477299. PMC 129718. PMID 12370428. 
  3. ^ Couture P, Thériault C, Simard J, Labrie F (January 1993). "Androgen receptor-mediated stimulation of 17 beta-hydroxysteroid dehydrogenase activity by dihydrotestosterone and medroxyprogesterone acetate in ZR-75-1 human breast cancer cells". Endocrinology 132 (1): 179–85. doi:10.1210/en.132.1.179. PMID 8380373. 
  4. ^ Laband P, Tresguerres JA, Lisboa BP, Volkwein U, Tamm J (August 1978). "The determination of 5alpha-androstane-3alpha, 17beta-diol in human plasma by radioimmunoassay". Acta Endocrinologica 88 (4): 778–86. PMID 581118.