1,4,6-Androstatrien-3,17-dione
1,4,6-Androstatrien-3,17-dione
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| 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 cat. |
X(US) |
| Legal status |
? (US) |
| Routes |
Parenteral |
| Pharmacokinetic data |
| Metabolism |
Hepatic |
| Half-life |
Minutes |
| Identifiers |
| CAS number |
633-35-2 |
| ATC code |
? |
| PubChem |
CID 104880 |
| ChemSpider |
94659 Y |
| Chemical data |
| Formula |
C19H22O2 |
| Mol. mass |
282 |
| SMILES |
eMolecules & PubChem |
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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
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Y(what is this?) (verify)
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1,4,6-Androstatrien-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
- ^ 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. doi:10.1210/endo-108-4-1597. PMID 7472286.
- ^ Adkins-Regan, Elizabeth; Cary H Leung (2006-07-06). "Sex steroids modulate changes in social and sexual preference during juvenile development in zebra finches". Hormones and Behaviour (Elsevier Inc) 50 (5): 772–778. doi:10.1016/j.yhbeh.2006.07.003. PMID 16919276. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6WGC-4KNMB80-2&_user=126523&_coverDate=12%2F31%2F2006&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_acct=C000010358&_version=1&_urlVersion=0&_userid=126523&md5=e8f6a30073440028b6141ba18340af16. Retrieved 2007-10-07.
- ^ Parr MK, Fusshöller G, Schlörer N, Opfermann G, Piper T, Rodchenkov G, Schänzer W (2009). "Metabolism of androsta-1,4,6-triene-3,17-dione and detection by gas chromatography/mass spectrometry in doping control". Rapid Commun Mass Spectrom 23 (2): 207–18. doi:10.1002/rcm.3861. PMID 19089863.
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.