11-Ketoandrosterone
Chemical compound
From Wikipedia, the free encyclopedia
11-Ketoandrosterone is an endogenous steroid.[1][2]
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| Names | |
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| IUPAC name
3α-Hydroxy-5α-androstane-11,17-dione | |
| 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 | |
| Identifiers | |
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| Properties | |
| C19H28O3 | |
| Molar mass | 304.430 g·molâ1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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[update].
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]
