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Revision as of 18:07, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 468728871 of page 4-Androstene-3,6,17-trione for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 12:08, 25 March 2024 edit DMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators186,371 edits auto mw 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 447560771 | verifiedrevid = 477221058
| IUPAC_name = (10R,13S)-10,13-dimethyl-<br>1,7,8,9,10,11,12,13,15,16-<br>decahydro-2H-cyclopentaphenanthrene-<br>3,6,17(14H)-trione | IUPAC_name = (10''R'',13''S'')-10,13-dimethyl-<br>1,7,8,9,10,11,12,13,15,16-decahydro-2''H''-cyclopentaphenanthrene-3,6,17(14''H'')-trione
| image = 4-Androstene-3,6,17-trione.png | image = 4-Androstene-3,6,17-trione.png


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| tradename = | tradename =
| pregnancy_category = | pregnancy_category =
| legal_status = Banned by ]<ref>{{cite web|url=http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf |title=The World Anti-Doping Code: The 2012 Prohibited List |publisher=] |access-date=2012-07-17 |url-status=dead |archive-url=https://web.archive.org/web/20120513020202/http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf |archive-date=2012-05-13 }}</ref>
| legal_status = unregulated, banned by World Anti-Doping Agency <ref></ref>
| routes_of_administration = oral | routes_of_administration = ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 2243-06-3 --> | CAS_number = 2243-06-3
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = L8L0381OBP
| ATC_prefix = | ATC_prefix =
| ATC_suffix = | ATC_suffix =
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<!--Chemical data--> <!--Chemical data-->
| C=19 | H=24 | O=3 | C=19 | H=24 | O=3
| molecular_weight = 300.39
| smiles = O=C4\C1=C\C(=O)CC1(3CC2(C(=O)CC23C4)C)C | smiles = O=C4\C1=C\C(=O)CC1(3CC2(C(=O)CC23C4)C)C
| InChI = 1/C19H24O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14H,3-8,10H2,1-2H3/t12-,13-,14-,18+,19-/m0/s1
| InChIKey = PJMNEPMSGCRSRC-IEVKOWOJBO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H24O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14H,3-8,10H2,1-2H3/t12-,13-,14-,18+,19-/m0/s1 | StdInChI = 1S/C19H24O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14H,3-8,10H2,1-2H3/t12-,13-,14-,18+,19-/m0/s1
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| StdInChIKey = PJMNEPMSGCRSRC-IEVKOWOJSA-N | StdInChIKey = PJMNEPMSGCRSRC-IEVKOWOJSA-N
}} }}

'''4-Androstene-3,6,17-trione''' ('''4-AT'''; also marketed as '''6-OXO''' or '''4-etioallocholen-3,6,17-trione''') is a ] or ] that may increase the testosterone-estrogen ratio, but has no proven effect on body composition. Its use can be detected in urine.<ref>{{cite journal | vauthors = Van Thuyne W, Van Eenoo P, Mikulcíková P, Deventer K, Delbeke FT | title = Detection of androst-4-ene-3,6,17-trione (6-OXO) and its metabolites in urine by gas chromatography-mass spectrometry in relation to doping analysis | journal = Biomedical Chromatography | volume = 19 | issue = 9 | pages = 689–695 | date = November 2005 | pmid = 15828056 | doi = 10.1002/bmc.496 }}</ref><ref>{{cite journal | vauthors = Deventer K, Van Eenoo P, Mikulcíková P, Van Thuyne W, Delbeke FT | title = Quantitative analysis of androst-4-ene-3,6,17-trione and metabolites in human urine after the administration of a food supplement by liquid chromatography/ion trap-mass spectrometry | journal = Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences | volume = 828 | issue = 1–2 | pages = 21–26 | date = December 2005 | pmid = 16213800 | doi = 10.1016/j.jchromb.2005.08.024 }}</ref>

4-AT is a potent irreversible ] that inhibits estrogen biosynthesis by permanently binding and inactivating aromatase in ] and peripheral tissue.<ref>{{cite journal | vauthors = Numazawa M, Tsuji M, Mutsumi A | title = Studies on aromatase inhibition with 4-androstene-3,6,17-trione: its 3 beta-reduction and time-dependent irreversible binding to aromatase with human placental microsomes | journal = Journal of Steroid Biochemistry | volume = 28 | issue = 3 | pages = 337–344 | date = September 1987 | pmid = 3657156 | doi = 10.1016/0022-4731(87)91028-4 }}</ref><ref>{{cite journal | vauthors = Covey DF, Hood WF | title = Enzyme-generated intermediates derived from 4-androstene-3,6,17-trione and 1,4,6-androstatriene-3,17-dione cause a time-dependent decrease in human placental aromatase activity | journal = Endocrinology | volume = 108 | issue = 4 | pages = 1597–1599 | date = April 1981 | pmid = 7472286 | doi = 10.1210/endo-108-4-1597 }}</ref><ref>{{cite journal | vauthors = Hsueh AJ, Erickson GF | title = Glucocorticoid inhibition of FSH-induced estrogen production in cultured rat granulosa cells | journal = Steroids | volume = 32 | issue = 5 | pages = 639–648 | date = December 1978 | pmid = 734698 | doi = 10.1016/0039-128X(78)90074-0 | s2cid = 23530490 }}</ref> ] is responsible for the conversion of ] to ]. Blocking aromatase causes the body to decrease in levels of estradiol, which then results in increase of ] and consequently, ]. Since testosterone has myotropic activity and estradiol does not, elevated testosterone levels increase muscle mass. However, there appear to be no human or animal studies testing the hypothesis that 4-AT will produce an anabolic effect.

4-AT is used by ] or ] users to counteract ] level increases caused by aromatization during their ]. This helps minimize side effects such as ] but can lead to ]. Also, after a steroid cycle, the compound may be used to shorten the recovery from the testicular suppression that can be the result of the use of steroids.

Baylor University conducted an eight-week study to determine the effects of 300&nbsp;mg or 600&nbsp;mg of 4-AT in resistance-trained males. Compared to baseline, free testosterone increased by 90% for 300&nbsp;mg group and 84% for 600&nbsp;mg group, respectively. Also ] and the ratio of ] to ] increased significantly. The report concluded that "he results of this study indicate that eight weeks of 6-OXO supplementation had no effect on body composition or clinical safety markers, but incompletely inhibited aromatase activity and significantly increased endogenous DHT levels that were attenuated after a three-week washout period".<ref name="Rohle2007">{{cite journal | vauthors = Rohle D, Wilborn C, Taylor L, Mulligan C, Kreider R, Willoughby D | title = Effects of eight weeks of an alleged aromatase inhibiting nutritional supplement 6-OXO (androst-4-ene-3,6,17-trione) on serum hormone profiles and clinical safety markers in resistance-trained, eugonadal males | journal = Journal of the International Society of Sports Nutrition | volume = 4 | pages = 13 | date = October 2007 | pmid = 17949492 | pmc = 2100070 | doi = 10.1186/1550-2783-4-13 | doi-access = free }}</ref> This study did not utilize a control group and was funded in part by two producers of commercial 4-AT.<ref name="Rohle2007" />

In a ]{{Citation needed|date=June 2009}} dated July 7, 2006, the ] (FDA) argues that marketing of 4-AT violates the Federal Food, Drug, and Cosmetic Act and as such products containing it are ''adulterated'' by legal definition.

In 2008, ] issued a warning that 4-AT had a health risk related to blood clotting and recommended all users immediately cease use.<ref>{{cite web | url = http://www.hc-sc.gc.ca/ahc-asc/media/advisories-avis/_2008/2008_93-eng.php | title = Health Canada warns consumers not to use the dietary supplements 6-OXO and 1-AD due to potential serious health risks | publisher = ] | date = June 18, 2008}}</ref>

== References ==
{{reflist}}

{{DEFAULTSORT:Androstene-3, 6, 17-trione, 4-}}
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