11β-Hydroxyandrostenedione

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11β-Hydroxyandrostenedione
11β-Hydroxyandrostenedione.svg
Names
Preferred 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-Hydroxyandrost-4-ene-3,17-dione; 11β-OHA4
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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
  • C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CCC4=O)C)O
Properties
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]

See also[edit]

References[edit]

  1. ^ a b 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.
  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. 75 (1): 183–192. doi:10.1161/HYPERTENSIONAHA.119.13866. PMC 7034384. PMID 31786984.