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11β-Hydroxyandrostenedione

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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-cyclopentaphenanthrene-1,7(3aH)-dione
Other names 11β-Hydroxy-4-androstenedione; 11β-OHA4
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: WSCUHXPGYUMQEX-KCZNZURUSA-N
SMILES
  • C12CCC(=O)C=C1CC32(C4(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 , 100 kPa). Infobox references
Chemical compound

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. 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.

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.

See also

References

  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.
  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.
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