11-Ketoandrosterone

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

11-Ketoandrosterone
Names
IUPAC name
(3α,5α)-3-Hydroxyandrostane-11,17-dione
Other names
11-Oxoandrosterone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
Properties
C19H28O3
Molar mass 304.430 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 is not known as of 2020.

Structure

11-Ketoandrosterone is a 11-keto form 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.[6]

Clinical relevance

11-Ketoandrosterone is a metabolite that may be biosynthesized within the androgen backdoor pathway, 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.[6]

See also

References
  1. van Rooyen D, Gent R, Barnard L, Swart AC (April 2018). "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. doi:10.1016/j.jsbmb.2017.12.014. PMID 29277707. S2CID 3700135.
  2. van Rooyen D, Yadav R, Scott EE, Swart AC (May 2020). "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. doi:10.1016/j.jsbmb.2020.105614. PMID 32007561. S2CID 210955834.
  3. "CHEBI:34134 - 11-Ketoandrosterone".
  4. Turcu AF, Nanba AT, Auchus RJ (2018). "The Rise, Fall, and Resurrection of 11-Oxygenated Androgens in Human Physiology and Disease". Hormone Research in Paediatrics. 89 (5): 284–291. doi:10.1159/000486036. PMC 6031471. PMID 29742491.
  5. Turcu AF, Rege J, Auchus RJ, Rainey WE (May 2020). "11-Oxygenated androgens in health and disease". Nature Reviews. Endocrinology. 16 (5): 284–296. doi:10.1038/s41574-020-0336-x. PMID 32203405. S2CID 212732699.
  6. Barnard L, Nikolaou N, Louw C, Schiffer L, Gibson H, Gilligan LC, Gangitano E, Snoep J, Arlt W, Tomlinson JW, Storbeck KH (September 2020). "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. doi:10.1016/j.jsbmb.2020.105724. PMID 32629108.
  7. Auchus RJ (November 2004). "The backdoor pathway to dihydrotestosterone". Trends in Endocrinology and Metabolism. 15 (9): 432–8. doi:10.1016/j.tem.2004.09.004. PMID 15519890. S2CID 10631647.
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