4-Androstene-3,6,17-trione

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4-Androstene-3,6,17-trione
Systematic (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
Identifiers
CAS number 120051-39-0
ATC code  ?
PubChem  ?
Chemical data
Formula C19H24O3 
Mol. mass 300.39
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?
Legal status

unregulated, banned by World Anti-Doping Agency [1]
Routes oral
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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.[2] [3]

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. [4][5][6] 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%.[7] The subjects took 300mg orally twice a day for four weeks without taking any other drugs or supplements.

Baylor University made a 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 ratio of free testosterone to estradiol increased significantly. [8][9].

In a warning letter[broken citation] 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.

[edit] Usage

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

[edit] References

  1. ^ The World
  2. ^ J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Dec 15;828(1-2):21-6 -Regarding detection of 6-OXO in urine
  3. ^ Van Thuyne W, Van Eenoo P, Mikulcíková P, Deventer K, Delbeke FT. (2005). "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.". Biomed Chromatogr. 19: 689. doi:10.1002/bmc.496. PMID 15828056. 
  4. ^ Numazawa M, Tsuji M, Mutsumi A (1987). "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". J Steroid Biochem. 28(3) (Sep): 337–44. doi:10.1016/0022-4731(87)91028-4. PMID 3657156. 
  5. ^ Covey DF, Hood WF. (1981). "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". Endocrinology 108 (4): 1597–9. PMID 7472286. 
  6. ^ Hsueh AJ, Erickson GF. (1978). "Glucocorticoid inhibition of FSH-induced estrogen production in cultured rat granulosa cells". Steroids 32 (5): 639–48. doi:10.1016/0039-128X(78)90074-0. PMID 734698. 
  7. ^ Patent application:"Use of 4-androstene-3,6,17-trione to elevate testosterone levels and the testosterone/estrogen ratio in males"
  8. ^ Rohle D, Wilborn C, Taylor L, Mulligan C, Kreider R, Willoughby D. (2007). "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.". J Int Soc Sports Nutr. 4: 13. doi:10.1186/1550-2783-4-13. PMID 17949492. 
  9. ^ Muscle & Fitness: The science of 6-OXO