ANDROSTA-1,4,6-TRIENE-3,17-DIONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H22O2
Molecular Weight	282.3768
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of ANDROSTA-1,4,6-TRIENE-3,17-DIONE

Structure Search

SMILES

C[C@]12CC[C@H]3[C@@H](C=CC4=CC(=O)C=C[C@]34C)[C@@H]1CCC2=O

InChI

InChIKey=DKVSUQWCZQBWCP-QAGGRKNESA-N

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

HIDE SMILES / InChI

Molecular Formula	C19H22O2
Molecular Weight	282.3768
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26031748 | https://www.ncbi.nlm.nih.gov/pubmed/16919276 | https://www.ncbi.nlm.nih.gov/pubmed/7472286

Androsta-1,4,6-triene-3,17-dione (ATD) is an irreversible steroidal aromatase inhibitor and is marketed as a supplement. It has been reported to effectively reduce estrogen biosynthesis and significantly increase the levels of endogenous steroids such as dihydrotestosterone and testosterone in human. ATD abuses have been reported in human sports. ATD is used to control estrogen synthesis. ATD inhibits estrogen biosynthesis by permanently binding and inactivating aromatase.

Approval Year

PubMed

Title	Date	PubMed
The aromatase inhibitor 1,4,6-androstatriene-3,17-dione (ATD) reduces disinhibitory behavior in intact adult male rats treated with a high dose of testosterone.	2010-01-20	19766145
The mild stress of chronic prenatal injections may have additive effects on drugs administered during pregnancy to alter brain sexual differentiation.	2010	21173740
Cryptic regulation of vasotocin neuronal activity but not anatomy by sex steroids and social stimuli in opportunistic desert finches.	2010	20332615
wnt4 Is associated with the development of ovarian tissue in the protandrous black Porgy, Acanthopagrus schlegeli.	2009-12	19605791
Sex steroids are necessary in the second postnatal week for the expression of male alloparental behavior in prairie voles (Microtus ochragaster).	2009-10	19824762
Effects of aromatase inhibitors and different doses of testosterone on gonadotropins in one year old male Atlantic salmon (Salmo salar).	2009-08	19345741
Estradiol shapes auditory processing in the adult brain by regulating inhibitory transmission and plasticity-associated gene expression.	2009-05-06	19420261
Involvement of estradiol-17beta and its membrane receptor, G protein coupled receptor 30 (GPR30) in regulation of oocyte maturation in zebrafish, Danio rario.	2009-03	18952087
Metabolism of androsta-1,4,6-triene-3,17-dione and detection by gas chromatography/mass spectrometry in doping control.	2009-01	19089863
Acoustic characteristics, early experience, and endocrine status interact to modulate female zebra finches' behavioral responses to songs.	2009-01	18804474
Perinatal inhibition of aromatization enhances the reward value of sex.	2008-08	18729639
Sex differences and effects of neonatal aromatase inhibition on masculine and feminine copulatory potentials in prairie voles.	2008-06	18378236
Rainbow trout gonadal masculinization induced by inhibition of estrogen synthesis is more physiological than masculinization induced by androgen supplementation.	2008-05	18199883
Endogenous oestradiol regulates progesterone receptor expression in the brain of female rat fetuses: what is the source of oestradiol?	2008-03	18208546
Effects of impaired testosterone metabolism during prenatal ontogenesis on the level of anxiety and behavior of rats in a novel environment.	2007-06	17505792
Chemoselective reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by various hydride reagents.	2007-04	17303200
Olfactory sensitivity through the course of psychosis: Relationships to olfactory identification, symptomatology and the schizophrenia odour.	2007-01-15	17156856
Characteristics of behavior and stress reactivity of the hypophyseal-adrenocortical system in rats with prenatal inhibition of testosterone metabolism.	2007-01	17180319
The discovery and mechanism of action of letrozole.	2007	17912633
Sex steroids modulate changes in social and sexual preference during juvenile development in zebra finches.	2006-12	16919276
Effects of aromatase inhibitors on in vitro steroidogenesis by Atlantic salmon (Salmo salar) gonadal and brain tissue.	2006-10	16870481
[Effects of prenatal disturbance in the brain testosterone metabolism on anxiety level and behavior of rats in a novel environment].	2006-07-28	16869267
The effect of aromatase inhibition on the sexual differentiation of the sheep brain.	2006-06	16943590
The role of sex steroids in courtship, pairing and pairing behaviors in the socially monogamous zebra finch.	2006-06	16581072
Alpha-fetoprotein protects the developing female mouse brain from masculinization and defeminization by estrogens.	2006-02	16388309
The role of aromatase inhibitors in ameliorating deleterious effects of ovarian stimulation on outcome of infertility treatment.	2005-10-04	16202169
[Behavioral activity and stress reaction of the pituitary-adrenocortical axis in rat with prenatal inhibition of testosterone metabolism].	2005-09	16353482
Separating behavioral and physiological mechanisms in testosterone-mediated trade-offs.	2005-08	16032571
Simultaneous treatment with an aromatase inhibitor and an anti-androgen decreases the likelihood of dawn song in free-living male great tits, Parus major.	2005-08	15878579
Epoxidation and reduction of DHEA, 1,4,6-androstatrien-3-one and 4,6-androstadien-3beta,17beta-diol.	2005-05-25	18007323
Organizational role for testosterone and estrogen on adult hypothalamic-pituitary-adrenal axis activity in the male rat.	2005-04	15625243
The effects of combined aromatase inhibitor and anti-androgen on male territorial aggression in a tropical population of rufous-collared sparrows, Zonotrichia capensis.	2004-01-15	14697309
Estrogen synthesis in fetal sheep brain: effect of maternal treatment with an aromatase inhibitor.	2003-02	12533398
Symposium: conference on the science and policy of performance-enhancing products.	2002-10	12370572
Sex differences in progesterone receptor expression: a potential mechanism for estradiol-mediated sexual differentiation.	2002-10	12239082
Aromatase inhibitors block natural sex change and induce male function in the protandrous black porgy, Acanthopagrus schlegeli Bleeker: possible mechanism of natural sex change.	2002-06	12021057
Effect of prenatal androgen receptor antagonist or aromatase inhibitor on sexual behavior, partner preference and neuronal Fos responses to estrous female odors in the rat accessory olfactory system.	2002-03	11897260
Seasonal differences in the hormonal control of territorial aggression in free-living European stonechats.	2002-02	11863378
Sex change in the protandrous black porgy, Acanthopagrus schlegeli: a review in gonadal development, estradiol, estrogen receptor, aromatase activity and gonadotropin.	2001-12-01	11748620
Regulation of plasma gonadotropin II secretion by sex steroids, aromatase inhibitors, and antiestrogens in the protandrous black porgy, Acanthopagrus schlegeli Bleeker.	2001-06	11399474

Sample Use Guides

In Vitro Use Guide

Androsta-1,4,6-triene-3,17-dione binds to the human placental aromatase with an apparent Ki of 0.18 uM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:30:33 GMT 2025` Edited by `admin` on `Mon Mar 31 21:30:33 GMT 2025`
Record UNII	217A6T1V8N
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

1,4,6 ETIOALLOCHOLAN-DIONE

Preferred Name

English

ANDROSTA-1,4,6-TRIENE-3,17-DIONE

Systematic Name

English

ATD

Common Name

English

Code System Code Type Description

PUBCHEM

104880