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Androgen
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==Types and examples== The main subset of androgens, known as adrenal androgens, is composed of 19-carbon steroids synthesized in the [[zona reticularis]], the innermost layer of the [[adrenal cortex]]. Adrenal androgens function as weak steroids (though some are precursors), and the subset includes [[dehydroepiandrosterone]] (DHEA), [[dehydroepiandrosterone sulfate]] (DHEA-S), [[androstenedione]] (A4), and [[androstenediol]] (A5). Besides testosterone, other androgens include: * Dehydroepiandrosterone (DHEA) is a steroid hormone produced in the adrenal cortex from [[cholesterol]].<ref>{{cite web | url=http://www.diasource-diagnostics.com/en/Products/ImmunoAssays/Fertility/Androgens | title=Androgens | publisher=DIAsource | access-date=26 June 2013 | archive-date=8 August 2014 | archive-url=https://web.archive.org/web/20140808035826/http://www.diasource-diagnostics.com/en/Products/ImmunoAssays/Fertility/Androgens | url-status=dead }}</ref> It is the primary precursor of both the androgen and [[estrogen]] sex hormones. DHEA is also called dehydroisoandrosterone or dehydroandrosterone. * Androstenedione (A4) is an androgenic steroid produced by the [[testes]], adrenal cortex, and [[ovaries]]. While androstenedione is converted metabolically to [[testosterone]] and other androgens, it is also the parent structure of [[estrone]]. Use of androstenedione as an athletic or [[bodybuilding supplement]] has been banned by the [[International Olympic Committee]], as well as other sporting organizations. * [[Androstenediol]] (A5) is a steroid [[metabolite]] of DHEA and the precursor to sex hormones [[testosterone]] and [[estradiol]]. * [[Androsterone]] is a chemical byproduct created during the breakdown of androgens, or derived from [[progesterone]], that also exerts minor masculinising effects, but with one-seventh the intensity of testosterone. It is found in approximately equal amounts in the [[blood plasma|plasma]] and [[urine]] of both males and females. * [[Dihydrotestosterone]] (DHT) is a metabolite of testosterone, and a more potent androgen than testosterone in that it binds more strongly to androgen receptors. It is produced in the skin and reproductive tissue. * A4 and testosterone can also have an extra hydroxyl (-OH) or ketone (=O) group bound on position 11. In this case you can have [[11-hydroxyandrostenedione]], [[11-ketoandrostenedione]], [[11-hydroxytestosterone]], and [[11-ketotestosterone]]. The latter has the same biological activity as testosterone<ref name = "Adriaansen_2024">{{cite journal | vauthors = Adriaansen BP, Oude Alink SE, Swinkels DW, SchrΓΆder MA, Span PN, Sweep FC, Claahsen-van der Grinten HL, van Herwaarden AE | display-authors = 6 | title = Reference intervals for serum 11-oxygenated androgens in children | journal = European Journal of Endocrinology | volume = 190 | issue = 1 | pages = 96β103 | date = January 2024 | pmid = 38243909 | doi = 10.1093/ejendo/lvae008 | doi-access = free | url = https://repository.ubn.ru.nl//bitstream/handle/2066/303614/303614.pdf }}</ref> and, therefore, these are also very important in healthy individuals and patients with diseases like, congenital adrenal hyperplasia, polycystic ovarian syndrome, or premature adrenarche.<ref name = "Adriaansen_2024" /> Determined by consideration of all biological assay methods ({{circa|1970}}):<ref name="BriggsBrotherton">{{cite book |last1=Briggs MH, Brotherton J |title=Steroid Biochemistry and Pharmacology |date=3 February 1970 |publisher=Academic Press |location=London |isbn=978-0-12-134650-8}}</ref> === Female ovarian and adrenal androgens === The ovaries and adrenal glands also produce androgens, but at much lower levels than the testes. Regarding the relative contributions of ovaries and adrenal glands to female androgen levels, in a study with six menstruating women the following observations have been made:<ref name="1974 Abraham Ovarian Adrenal Androgens">{{cite journal | vauthors = Abraham GE | title = Ovarian and adrenal contribution to peripheral androgens during the menstrual cycle | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 39 | issue = 2 | pages = 340β346 | date = August 1974 | pmid = 4278727 | doi = 10.1210/jcem-39-2-340 }}</ref> * Adrenal contribution to peripheral T, DHT, A, DHEA and DHEA-S is relatively constant throughout the [[menstrual cycle]]. * Ovarian contribution of peripheral T, A and DHEA-S reaches maximum levels at mid-cycle, whereas ovarian contribution to peripheral DHT and DHEA does not seem to be influenced by the menstrual cycle. * Ovary and adrenal cortex contribute equally to peripheral T, DHT and A, with the exception that at mid-cycle ovarian contribution of peripheral A is twice that of the adrenal. * Peripheral DHEA and DHEA-S are produced mainly in the adrenal cortex which provides 80% of DHEA and over 90% of DHEA-S. {| class="wikitable" |+ Ovarian and adrenal contribution to peripheral androgens during the menstrual cycle<ref name="1974 Abraham Ovarian Adrenal Androgens"/> ! Androgen || '''Ovarian (%) (F, M, L)''' || '''Adrenal (%)''' |- | DHEA || 20 || 80 |- | DHEA-S || 4, 10, 4 || 90β96 |- | Androstenedione || 45, 70, 60 || 30β55 |- | Testosterone || 33, 60, 33 || 40β66 |- | DHT || 50 || 50 |- | colspan="3" | F = early follicular, M = midcycle, L = late luteal phase. |}
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