11-Ketoandrosterone Explained

11-Ketoandrosterone is an endogenous steroid.[1] [2]

Function

11-Ketoandrosterone is an androgen.[3] Androgens are sex hormones that stimulate or control the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. However, the potency of 11-ketoandrosterone as an agonist of androgen receptors was not known .

Structure

11-Ketoandrosterone is a 11-keto form and a metabolite of androsterone.

11-Ketoandrosterone belongs to a group of 11-oxyandrogens, i.e. 11-oxygenated (oxygen atom on C11 position forms a ketone group) 19-carbon steroids. 11-oxyandrogens are potent and clinically relevant agonists of the androgen receptors.[4] Potency of 11-ketotestosterone, an 11-oxyandrogen, is similar to that of testosterone.[5] 11-ketotestosterone, derived from 11β-hydroxyandrostenedione, may serve as the main androgen for healthy women.

Clinical relevance

11-Ketoandrosterone is a metabolite that may be biosynthesized within the androgen backdoor pathway,[6] a metabolic pathway for androgen synthesis that bypasses testosterone as an intermediate product.[7] [1] [2]

SRD5A2 catalyzes the 5α-reduction of 11-ketotestosterone that terminates at 11-ketoandrosterone, but only causes a small amount of 11-ketotestosterone inactivation. However, since the metabolism of the glucocorticoid cortisol also produces 11-ketocholosterone, 11-ketoandrosterone may be considered as a more specific urinary marker for the production of 11-ketotestosterone.[8]

See also

References

  1. van Rooyen D, Gent R, Barnard L, Swart AC . 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 . April 2018 . 29277707 . 10.1016/j.jsbmb.2017.12.014. 3700135 .
  2. van Rooyen D, Yadav R, Scott EE, Swart AC . CYP17A1 exhibits 17αhydroxylase/17,20-lyase activity towards 11β-hydroxyprogesterone and 11-ketoprogesterone metabolites in the C11-oxy backdoor pathway . The Journal of Steroid Biochemistry and Molecular Biology . 199 . 105614 . May 2020 . 32007561 . 10.1016/j.jsbmb.2020.105614. 210955834 .
  3. Web site: CHEBI:34134 - 11-Ketoandrosterone . 22 October 2020 . 24 October 2020 . https://web.archive.org/web/20201024215204/https://www.ebi.ac.uk/chebi/searchId.do?chebiId=34134 . live .
  4. Turcu AF, Nanba AT, Auchus RJ . The Rise, Fall, and Resurrection of 11-Oxygenated Androgens in Human Physiology and Disease . Hormone Research in Paediatrics . 89 . 5 . 284–291 . 2018 . 29742491 . 6031471 . 10.1159/000486036 .
  5. Turcu AF, Rege J, Auchus RJ, Rainey WE . 11-Oxygenated androgens in health and disease . Nature Reviews. Endocrinology . 16 . 5 . 284–296 . May 2020 . 32203405 . 10.1038/s41574-020-0336-x . 212732699 . 7881526 .
  6. 10.15347/WJM/2023.003 . free . Alternative androgen pathways . 3 April 2023 . Masiutin MM, Yadav MK . WikiJournal of Medicine . 10 . 29 . 257943362 .
  7. Auchus RJ . The backdoor pathway to dihydrotestosterone . Trends in Endocrinology and Metabolism . 15 . 9 . 432–8 . November 2004 . 15519890 . 10.1016/j.tem.2004.09.004. 10631647 .
  8. Barnard L, Nikolaou N, Louw C, Schiffer L, Gibson H, Gilligan LC, Gangitano E, Snoep J, Arlt W, Tomlinson JW, Storbeck KH . The A-ring reduction of 11-ketotestosterone is efficiently catalysed by AKR1D1 and SRD5A2 but not SRD5A1 . The Journal of Steroid Biochemistry and Molecular Biology . 202 . 105724 . September 2020 . 32629108 . 10.1016/j.jsbmb.2020.105724 . free . 11573/1490727 . free .

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