11-Ketoandrosterone

11-Ketoandrosterone
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
CAS Number	1231-82-9;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34134;
ChemSpider	92167;
KEGG	C14671;
PubChem CID	102029;
UNII	3T4E87JT27;
CompTox Dashboard (EPA)	DTXSID901043038 ;
	InChI 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;
	SMILES C[C@]12CC(=O)[C@H]3[C@@H](CC[C@H]4C[C@H](O)CC[C@]34C)[C@@H]1CCC2=O;
Properties
Chemical formula	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^[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]

References

^ ^a ^b 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.
^ ^a ^b 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.
^ "CHEBI:34134 - 11-Ketoandrosterone". Archived from the original on 24 October 2020. Retrieved 22 October 2020.
^ ^a ^b Masiutin MM, Yadav MK (3 April 2023). "Alternative androgen pathways" (PDF). WikiJournal of Medicine. 10: 29. doi:10.15347/WJM/2023.003. S2CID 257943362. This article incorporates text from this source, which is available under the CC BY 4.0 license.
^ 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.
^ 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. PMC 7881526. PMID 32203405. S2CID 212732699.
^ ^a ^b 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. hdl:11573/1490727. PMID 32629108.
^ 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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[pmid29277707-1] 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.

[pmid32007561-2] 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.

[chebi34134-3] "CHEBI:34134 - 11-Ketoandrosterone". Archived from the original on 24 October 2020. Retrieved 22 October 2020.

[wj-4] Masiutin MM, Yadav MK (3 April 2023). "Alternative androgen pathways" (PDF). WikiJournal of Medicine. 10: 29. doi:10.15347/WJM/2023.003. S2CID 257943362. This article incorporates text from this source, which is available under the CC BY 4.0 license.

[pmid29742491-5] 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.

[pmid32203405-6] 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. PMC 7881526. PMID 32203405. S2CID 212732699.

[pmid32629108-7] 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. hdl:11573/1490727. PMID 32629108.

[pmid15519890-8] 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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Function

Structure

Clinical relevance

See also

References