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Androgens and anabolic steroids
11-Ketoandrosterone
Другие языки:

    11-Ketoandrosterone

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    11-Ketoandrosterone
    11-Ketoandrosterone.svg
    Names
    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
    3D model (JSmol)
    ChEBI
    ChemSpider
    KEGG
    PubChem CID
    UNII
    • InChI=1S/C19H28O3/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/h11-14,17,20H,3-10H2,1-2H3/t11-,12+,13-,14-,17+,18-,19-/m0/s1
    • C[C@]12CC(=O)[C@H]3[C@@H](CC[C@H]4C[C@H](O)CC[C@]34C)[C@@H]1CCC2=O
    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).

    11-Ketoandrosterone is an endogenous steroid.

    Function

    11-Ketoandrosterone is an androgen. 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. Potency of 11-ketotestosterone, an 11-oxyandrogen, is similar to that of testosterone. 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, a metabolic pathway for androgen synthesis that bypasses testosterone as an intermediate product.

    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.

    See also


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