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11β-Hydroxydihydrotestosterone
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December 2023vanc
property raw P117 skin-invert-image 11β,17β-dihydroxy-5α-androstan-3-one (5S,8S,9S,10S,11S,13S,14S,17S)-11,17-dihydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one 5α-androstan-11β,17β-diol-3-one 7801-30-1 correct CAS correct FDA 10018051 8193624 InChI=1S/C19H30O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h11,13-17,21-22H,3-10H2,1-2H3/t11-,13-,14-,15-,16-,17+,18-,19-/m0/s1 C1CC(=O)C[C@]2([H])CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)C[C@H](O)[C@]3([H])[C@@]12C
19 30 3 08 Danger 351 360 201 202 281 308+313 405 501
11β-Hydroxydihydrotestosterone (11OHDHT) is an endogenous steroid.Storbeck KH, Bloem LM, Africander D, Schloms L, Swart P, Swart AC 11β-Hydroxydihydrotestosterone and 11-ketodihydrotestosterone, novel C19 steroids with androgenic activity: a putative role in castration resistant prostate cancer? Mol Cell Endocrinol 377 1–2 135–46 September 2013 23856005 10.1016/j.mce.2013.07.006 11740484 Although it may not have significant androgenic activity, it may still be an important precursor to androgenic molecules.Gent R, Van Rooyen D, Atkin SL, Swart AC C11-hydroxy and C11-oxo C19 and C21 Steroids: Pre-Receptor Regulation and Interaction with Androgen and Progesterone Steroid Receptors Int J Mol Sci 25 1 December 2023 101 38203272 10778819 10.3390/ijms25010101 freeby4 yes
Biological role
11OHDHT, along with other carbon-11-oxygenated (C11-oxy) steroids, 11-ketodihydrotestosterone (11KDHT) and 11-ketotestosterone (11KT), are androgen receptor (AR) agonists. The interconversion of C11-oxy C19 steroids, which includes 11OHDHT, was found to be more efficient than that of C11-oxy C21 steroids. 11OHDHT was also found to exhibit antagonism towards the progesterone receptor B (PRB), although it is not a pregnane (C21) steroid, highlighting the complex relationship between receptors and active as well as "inactive" C11-oxy steroids.
See also
Dihydrotestosterone
Steroid 11β-hydroxylase
11-Ketodihydrotestosterone
11β-Hydroxytestosterone
External links
An entry in the LIPID MAPS database: https://www.lipidmaps.org/databases/lmsd/LMST02020136
References
Category:5α-Reduced steroid metabolites
Category:Androstanes
Category:Cyclopentanols
Category:Ketones