11-Ketoandrosterone

December 2023 vanc property raw P117 3α-Hydroxy-5α-androstane-11,17-dione (3aS,3bS,5aS,7R,9aS,9bS,11aS)-7-Hydroxy-9a,11a-dimethyltetradecahydro-1H-cyclopenta[a]phenanthrene-1,10(2H)-dione 11-Oxoandrosterone 92167 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 1231-82-9 3T4E87JT27 34134 C14671 102029 C[C@]12CC(=O)[C@H]3[C@@H](CC[C@H]4C[C@H](O)CC[C@]34C)[C@@H]1CCC2=O 19 28 3 11-Ketoandrosterone is an endogenous steroid. 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 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 Function 11-Ketoandrosterone is an androgen.https://www.ebi.ac.uk/chebi/searchId.do?chebiId=34134 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 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 2020 y. 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. 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 Potency of 11-ketotestosterone, an 11-oxyandrogen, is similar to that of testosterone. 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 11-ketotestosterone, derived from 11β-hydroxyandrostenedione, may be the main androgen for healthy women. Clinical relevance 11-Ketoandrosterone is a metabolite that may be biosynthesized within the androgen backdoor pathway,10.15347/WJM/2023.003 free Alternative androgen pathways 3 April 2023 Masiutin MM, Yadav MK WikiJournal of Medicine 10 29 257943362 https://upload.wikimedia.org/wikiversity/en/a/a7/Alternative_androgens_pathways.pdfby4 yes a metabolic pathway for androgen synthesis that bypasses testosterone as an intermediate product. 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 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-ketoandrosterone, 11-ketoandrosterone may be considered as a more specific urinary marker for the production of 11-ketotestosterone. 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 See also Androgen backdoor pathway Androsterone References Category:Human metabolites Category:Secondary alcohols Category:Androgens Category:Androstanes Category:Hormones of the suprarenal cortex Category:Ketones