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
CAS Number	7801-30-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	8193624;
PubChem CID	10018051;
	InChI 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;
	SMILES 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
Chemical formula	C19H30O3
Molar mass	306.446 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H351, H360
Precautionary statements	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 is an endogenous steroid.^[1]^[2]^[3] Although it may not have significant androgenic activity, it may still be an important precursor to androgenic molecules.^[3]^[4]

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) stroid, highlighting the intricate interplay between receptors and active as well as "inactive" C11-oxy steroids.^[4]

External links

An entry in the LIPID MAPS database: https://www.lipidmaps.org/databases/lmsd/LMST02020136

References

^ 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.
^ Van Rooyen D, Gent R, Barnard L, Swart AC (2018). "The in vitro metabolism of 11β-hydroxyprogesterone and 11-ketoprogesterone to 11-ketodihydrotestosterone in the backdoor pathway". The Journal of Steroid Biochemistry and Molecular Biology. 178: 203–212. doi:10.1016/j.jsbmb.2017.12.014. PMID 29277707. S2CID 3700135.
^ ^a ^b Masiutin MM, Yadav MK (3 April 2023). "Alternative androgen pathways" (PDF). WikiJournal of Medicine. 10: 29. doi:10.15347/WJM/2023.003. S2CID 257943362. Archived (PDF) from the original on 24 October 2023. Retrieved 10 April 2024. This article incorporates text from this source, which is available under the CC BY 4.0 license.
^ ^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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[pmid23856005-1] 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.

[pmid29277707-2] Van Rooyen D, Gent R, Barnard L, Swart AC (2018). "The in vitro metabolism of 11β-hydroxyprogesterone and 11-ketoprogesterone to 11-ketodihydrotestosterone in the backdoor pathway". The Journal of Steroid Biochemistry and Molecular Biology. 178: 203–212. doi:10.1016/j.jsbmb.2017.12.014. PMID 29277707. S2CID 3700135.

[wj-3] Masiutin MM, Yadav MK (3 April 2023). "Alternative androgen pathways" (PDF). WikiJournal of Medicine. 10: 29. doi:10.15347/WJM/2023.003. S2CID 257943362. Archived (PDF) from the original on 24 October 2023. Retrieved 10 April 2024. This article incorporates text from this source, which is available under the CC BY 4.0 license.

[pmid38203272-4] 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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[2]

[3]

[4]

Biological role

See also

External links

References