11β-Hydroxyandrostenedione

11β-Hydroxyandrostenedione
Names
	IUPAC name (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
	Other names 11β-Hydroxy-4-androstenedione; 11β-Hydroxyandrost-4-ene-3,17-dione; 11β-OHA4
Identifiers
CAS Number	382-44-5;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27967;
ChEMBL	ChEMBL2311170;
ChemSpider	84958;
PubChem CID	94141;
UNII	41G81C896T;
CompTox Dashboard (EPA)	DTXSID8040931 ;
	InChI InChI=1S/C19H26O3/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/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15-,17+,18-,19-/m0/s1 Key: WSCUHXPGYUMQEX-KCZNZURUSA-N;
	SMILES C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CCC4=O)C)O;
Properties
Chemical formula	C19H26O3
Molar mass	302.414 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

11β-Hydroxyandrostenedione (11β-OHA4), also known as 11β-hydroxyandrost-4-ene-3,17-dione, is an endogenous, naturally occurring steroid and androgen prohormone that is produced primarily, if not exclusively, in the adrenal glands.[1] It is closely related to adrenosterone (11-ketoandrostenedione; 11-KA4), 11-ketotestosterone (11-KT), and 11-ketodihydrotestosterone (11-KDHT), which are also produced in the adrenal glands.[1]

It can be used as a biomarker for guiding primary aldosteronism subtyping in adrenal vein sampling where blood samples are taken from both adrenal glands to compare the amount of hormone made by each gland.[2]

References

Pretorius E, Arlt W, Storbeck K (2016). "A new dawn for androgens: Novel lessons from 11-oxygenated C19 steroids" (PDF). Molecular and Cellular Endocrinology. 441: 76–85. doi:10.1016/j.mce.2016.08.014. ISSN 0303-7207. PMID 27519632. S2CID 4079662.
Turcu AF, Wannachalee T, Tsodikov A, Nanba AT, Ren J, Shields JJ, O'Day PJ, Giacherio D, Rainey WE, Auchus RJ (2020). "Comprehensive Analysis of Steroid Biomarkers for Guiding Primary Aldosteronism Subtyping". Hypertension (Dallas, Tex. : 1979). 75 (1): 183–192. doi:10.1161/HYPERTENSIONAHA.119.13866. PMC 7034384. PMID 31786984.

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[PretoriusArlt2016-1] Pretorius E, Arlt W, Storbeck K (2016). "A new dawn for androgens: Novel lessons from 11-oxygenated C19 steroids" (PDF). Molecular and Cellular Endocrinology. 441: 76–85. doi:10.1016/j.mce.2016.08.014. ISSN 0303-7207. PMID 27519632. S2CID 4079662.

[pmid31786984-2] Turcu AF, Wannachalee T, Tsodikov A, Nanba AT, Ren J, Shields JJ, O'Day PJ, Giacherio D, Rainey WE, Auchus RJ (2020). "Comprehensive Analysis of Steroid Biomarkers for Guiding Primary Aldosteronism Subtyping". Hypertension (Dallas, Tex. : 1979). 75 (1): 183–192. doi:10.1161/HYPERTENSIONAHA.119.13866. PMC 7034384. PMID 31786984.

11β-Hydroxyandrostenedione

See also

References