4-Androstene-3,6,17-trione

drugbox
IUPAC_name = (10R,13S)-10,13-dimethyl-
1,7,8,9,10,11,12,13,15,16-
decahydro-2H-cyclopenta [alpha] phenanthrene-
3,6,17(14H)-trione


CAS_number = 2243-06-3
ATC_prefix =
ATC_suffix =
PubChem =
DrugBank =
C=19 | H=24 | O=3
molecular_weight = 300.39
bioavailability =
metabolism =
elimination_half-life =
excretion =
pregnancy_category =
legal_status = unregulated, banned by World Anti-Doping Agency [ [http://www.wada-ama.org/rtecontent/document/2008_List_En.pdf The World ] ]
routes_of_administration = oral

4-Androstene-3,6,17-trione (also marketed as "6-OXO" or 4-etioallocholen-3,6,17-trione) is a drug or nutritional supplement that may increase the testosterone-estrogen ratio. Its use can be detected in urine. [J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Dec 15;828(1-2):21-6 -Regarding detection of 6-OXO in urine] [cite journal |author=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=Biomed Chromatogr. |year=2005 |pmid=15828056 |doi=10.1002/bmc.496 |volume=19 |pages=689]

4-Androstene-3,6,17-trione (4-AT) is a potent irreversible aromatase inhibitor that inhibits estrogen biosynthesis by permanently binding and inactivating aromatase in adipose and peripheral tissue. [cite journal|author=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=J Steroid Biochem.|year=1987|issue=Sep|volume=28(3)|pages=337–44 |pmid=3657156|doi=10.1016/0022-4731(87)91028-4 ] [cite journal|author=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 |year=1981 |issue=4 |volume=108 |pages=1597–9 |pmid=7472286 ] [cite journal|author=Hsueh AJ, Erickson GF. |title=Glucocorticoid inhibition of FSH-induced estrogen production in cultured rat granulosa cells |journal=Steroids |year=1978 |issue=5 |volume=32 |pages=639–48 |pmid=734698 |doi=10.1016/0039-128X(78)90074-0 ] Aromatase is responsible for the conversion of testosterone to estradiol. Blocking aromatase causes the body to decrease in levels of estradiol, which then results in increase of LH and consequently, testosterone. 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 also used by steroid or prohormone users to counteract estrogen level increases caused by aromatization during their steroid cycle. This helps minimize side effects such as gynecomastia but can lead to acne. 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.

A recent United States patent application claims an 88% increase in plasma testosterone levels in men, while decreasing estrogen levels by 11%. [ [http://www.freshpatents.com/Use-of-4-androstene-3617-trione-to-elevate-testosterone-levels-and-the-testosterone-estrogen-ratio-in-males-dt20050317ptan20050059646.php?type=description Patent application:"Use of 4-androstene-3,6,17-trione to elevate testosterone levels and the testosterone/estrogen ratio in males"] ] The subjects took 300mg orally twice a day for four weeks without taking any other drugs or supplements.

Baylor University conducted an eight-week study to determine the effects of 300 mg or 600 mg of 6-OXO in resistance-trained males. Compared to baseline, free testosterone increased by 90% for 300 mg group and 84% for 600 mg group, respectively. Also dihydrotestosterone and the ratio of free testosterone to estradiol increased significantly. [cite journal |author=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. |year=2007 |journal=J Int Soc Sports Nutr. |pmid=17949492 |doi=10.1186/1550-2783-4-13 |volume=4 |pages=13] [ [http://www.findarticles.com/p/articles/mi_m0801/is_7_65/ai_n6074719 Muscle & Fitness: The science of 6-OXO] ] .

In a [http://www.fda.gov/foi/warning_letters/archive/g5935d.pdf warning letter] dated July 7, 2006, the FDA argues that marketing of 4-AT (aka, 6-OXO) violates the Federal Food, Drug, and Cosmetic Act and as such products containing it are "adulterated" by legal definition.

Usage

A typical dosage regimen is 200-600mg orally once a day in the evening, for a 4-6 week cycle.

References