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

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

1,4,6-Androstatriene-3,17-dione
Clinical data
Pregnancy category	US: X (Contraindicated)
Routes of administration	Oral
Legal status
Legal status	US: Supplement
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	48 hours
Identifiers
IUPAC name (8R,9S,10R,13S,14S)-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthrene-3,17-dione
CAS Number	633-35-2 ^[11]
PubChemCID	104880 ^[12]
ChemSpider	94659 ^[13]^Y
ChEBI	CHEBI:131190 ^[14]^Y
Chemical and physical data
Formula	C₁₉H₂₂O₂
Molar mass	282 g·mol⁻¹
3D model (JSmol)	Interactive image ^[15]
SMILES O=C\4\C=C/[C@]3(C(/C=C[C@H]2[C@H]1C@@(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
(verify) ^[16]

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 was present in some over-the-counter bodybuilding supplements until 2009 as well as Topical ATD solutions that work transdermally. The product was developed and commercialized in the dietary supplement market place by industry journeyman, Bruce Kneller who holds a United States Patent for use of the compound and related compounds (#7,939,517) and Gaspari Nutrition. 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 possible metabolite and production contaminant and is also prohibited in amateur and professional sports which forbids aromatase inhibitors.^[3]

A related agent is exemestane (Aromasin).

1,4,6-Androstatriene-3,17-dione
Clinical data
Pregnancy category	US: X (Contraindicated)
Routes of administration	Oral
Legal status
Legal status	US: Supplement
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	48 hours
Identifiers
IUPAC name (8R,9S,10R,13S,14S)-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthrene-3,17-dione
CAS Number	633-35-2 ^[11]
PubChemCID	104880 ^[12]
ChemSpider	94659 ^[13]^Y
ChEBI	CHEBI:131190 ^[14]^Y
Chemical and physical data
Formula	C₁₉H₂₂O₂
Molar mass	282 g·mol⁻¹
3D model (JSmol)	Interactive image ^[15]
SMILES O=C\4\C=C/[C@]3(C(/C=C[C@H]2[C@H]1C@@(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
(verify) ^[16]

References

[1]

Citation Link//www.ncbi.nlm.nih.gov/pubmed/7472286Covey, 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.

Sep 21, 2019, 11:12 AM

[2]

Citation Linkwww.sciencedirect.comAdkins-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 Behavior. Elsevier Inc. 50 (5): 772–778. doi:10.1016/j.yhbeh.2006.07.003. PMID 16919276. Archived from the original on 2013-01-04. Retrieved 2007-10-07.

Sep 21, 2019, 11:12 AM

[3]

Citation Link//www.ncbi.nlm.nih.gov/pubmed/19089863Parr 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.

Sep 21, 2019, 11:12 AM

[4]

Citation Linkwww.commonchemistry.org633-35-2

Sep 21, 2019, 11:12 AM

[5]

Citation Linkpubchem.ncbi.nlm.nih.gov104880

Sep 21, 2019, 11:12 AM

[6]

Citation Linkwww.chemspider.com94659

Sep 21, 2019, 11:12 AM

[7]

Citation Linkwww.ebi.ac.ukCHEBI:131190