Chemistry:11-Ketoandrosterone
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| IUPAC name
3α-Hydroxy-5α-androstane-11,17-dione
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| Systematic IUPAC name
(3aS,3bS,5aS,7R,9aS,9bS,11aS)-7-Hydroxy-9a,11a-dimethyltetradecahydro-1H-cyclopenta[a]phenanthrene-1,10(2H)-dione | |
| Other names
11-Oxoandrosterone
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| Identifiers | |
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| 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 | |
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 (As of 2020).
Structure
11-Ketoandrosterone is a 11-keto form and a metabolite of androsterone.[4]
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.[5] Potency of 11-ketotestosterone, an 11-oxyandrogen, is similar to that of testosterone.[6] 11-ketotestosterone, derived from 11β-hydroxyandrostenedione, may serve as the main androgen for healthy women.[7]
Clinical relevance
11-Ketoandrosterone is a metabolite that may be biosynthesized within the androgen backdoor pathway,[4] a metabolic pathway for androgen synthesis that bypasses testosterone as an intermediate product.[8][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.[7]
See also
References
- ↑ 1.0 1.1 "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. doi:10.1016/j.jsbmb.2017.12.014. PMID 29277707.
- ↑ 2.0 2.1 "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. doi:10.1016/j.jsbmb.2020.105614. PMID 32007561.
- ↑ "CHEBI:34134 - 11-Ketoandrosterone". https://www.ebi.ac.uk/chebi/searchId.do?chebiId=34134.
- ↑ 4.0 4.1 "Alternative androgen pathways". WikiJournal of Medicine 10: X. 2023. doi:10.15347/WJM/2023.003.
- ↑ "The Rise, Fall, and Resurrection of 11-Oxygenated Androgens in Human Physiology and Disease". Hormone Research in Paediatrics 89 (5): 284–291. 2018. doi:10.1159/000486036. PMID 29742491.
- ↑ "11-Oxygenated androgens in health and disease". Nature Reviews. Endocrinology 16 (5): 284–296. May 2020. doi:10.1038/s41574-020-0336-x. PMID 32203405.
- ↑ 7.0 7.1 "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. doi:10.1016/j.jsbmb.2020.105724. PMID 32629108.
- ↑ "The backdoor pathway to dihydrotestosterone". Trends in Endocrinology and Metabolism 15 (9): 432–8. November 2004. doi:10.1016/j.tem.2004.09.004. PMID 15519890.
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