11β-Hydroxyandrostenedione

11β-Hydroxyandrostenedione
Names
	IUPAC name 11β-Hydroxyandrost-4-ene-3,17-dione
	Systematic IUPAC name (3aS,3bS,9aR,9bS,10S,11aS)-10-Hydroxy-9a,11a-dimethyl-2,3,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[a]phenanthrene-1,7(3aH)-dione
	Other names 11β-Hydroxy-4-androstenedione; 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

^ ^a ^b Pretorius, Elzette; Arlt, Wiebke; Storbeck, Karl-Heinz (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, A. F.; Wannachalee, T.; Tsodikov, A.; Nanba, A. T.; Ren, J.; Shields, J. J.; O'Day, P. J.; Giacherio, D.; Rainey, W. E.; Auchus, R. J. (2020). "Comprehensive Analysis of Steroid Biomarkers for Guiding Primary Aldosteronism Subtyping". Hypertension. 75 (1): 183–192. doi:10.1161/HYPERTENSIONAHA.119.13866. PMC 7034384. PMID 31786984.

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[pmid27519632-1] Pretorius, Elzette; Arlt, Wiebke; Storbeck, Karl-Heinz (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, A. F.; Wannachalee, T.; Tsodikov, A.; Nanba, A. T.; Ren, J.; Shields, J. J.; O'Day, P. J.; Giacherio, D.; Rainey, W. E.; Auchus, R. J. (2020). "Comprehensive Analysis of Steroid Biomarkers for Guiding Primary Aldosteronism Subtyping". Hypertension. 75 (1): 183–192. doi:10.1161/HYPERTENSIONAHA.119.13866. PMC 7034384. PMID 31786984.

[1]

[2]

11β-Hydroxyandrostenedione

See also

References