11β-Hydroxydihydrotestosterone

11β-Hydroxydihydrotestosterone
Names
IUPAC name
11β,17β-dihydroxy-5α-androstan-3-one
Systematic IUPAC name
(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
Other names
5α-androstan-11β,17β-diol-3-one
Identifiers
3D model (JSmol)
ChemSpider
  • 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
Properties
C19H30O3
Molar mass 306.446 g·mol−1
Hazards
GHS labelling:
Danger
H351, H360
P201, P202, P281, P308+P313, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

11β-Hydroxydihydrotestosterone (11OHDHT) is an endogenous steroid.[1] Although it may not have significant androgenic activity, it may still be an important precursor to androgenic molecules.[2]

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 intricate interplay between receptors and active as well as "inactive" C11-oxy steroids.[2]

See also

References

  1. ^ Storbeck KH, Bloem LM, Africander D, Schloms L, Swart P, Swart AC (September 2013). "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. doi:10.1016/j.mce.2013.07.006. PMID 23856005. S2CID 11740484.
  2. ^ a b Gent R, Van Rooyen D, Atkin SL, Swart AC (December 2023). "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): 101. doi:10.3390/ijms25010101. PMC 10778819. PMID 38203272. This article incorporates text from this source, which is available under the CC BY 4.0 license.
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