1,4,6-Androstatriene-3,17-dione

1,4,6-Androstatriene-3,17-dione

Systematic (IUPAC) name
(8R,9S,10R,13S,14S)-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthrene-3,17-dione
Clinical data
Pregnancy category	US: X (Contraindicated)
Legal status	US: Supplement
Routes of administration	Oral
Pharmacokinetic data
Metabolism	Hepatic
Half-life	48 hours
Identifiers
CAS Registry Number	633-35-2
PubChem	CID 104880
ChemSpider	94659 Y
Chemical data
Formula	C19H22O2
Molecular mass	282
SMILES O=C\4\C=C/[C@]3(C(/C=C\[C@H]2[C@H]1[C@@](C(=O)CC1)(CC[C@@H]23)C)=C/4)C
InChI InChI=1S/C19H22O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3-4,7,9,11,14-16H,5-6,8,10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1  Y Key:DKVSUQWCZQBWCP-QAGGRKNESA-N  Y
Y (what is this?)  (verify)

1,4,6-Androstatriene-3,17-dione (ATD) is a potent irreversible aromatase inhibitor that inhibits estrogen biosynthesis by permanently binding and inactivating aromatase in adipose and peripheral tissue.^[1] It is used to control estrogen synthesis.^[2]

ATD is present in some over-the-counter bodybuilding supplements as well as Topical ATD solutions that work transdermally. While not banned, ATD may cause positive urinalysis results leading to disqualification from competitive sports. ATD has many names in sports supplements including: 1,4,6 etiollochan-dione, 3, 17-keto-etiochol-triene, androst-1,4,6-triene-3,17-dione and many others. These all refer to CAS# 633-35-2.

ATD may cause a positive test for the anabolic steroid boldenone, of which it is a metabolite and is also prohibited in amateur and professional sports which forbids aromatase inhibitors.^[3]

A related agent is exemestane (Aromasin).

References

Further reading

• Ellinwood WE, Hess DL, Roselli CE, Spies HG, Resko JA (1984). "Inhibition of aromatization stimulates luteinizing hormone and testosterone secretion in adult male rhesus monkeys". J. Clin. Endocrinol. Metab. 59 (6): 1088–96. doi:10.1210/jcem-59-6-1088. PMID 6541658.