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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H28O2
Molecular Weight 288.4251
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROANDROSTENEDIONE

SMILES

C[C@@]12CCC(=O)C[C@]2([H])CC[C@@]3([H])[C@]4([H])CCC(=O)[C@@]4(C)CC[C@@]31[H]

InChI

InChIKey=RAJWOBJTTGJROA-WZNAKSSCSA-N
InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H28O2
Molecular Weight 288.4251
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/22064602 | https://www.ncbi.nlm.nih.gov/pubmed/3783591 | https://www.ncbi.nlm.nih.gov/pubmed/28733189 | https://www.ncbi.nlm.nih.gov/pubmed/27449532 | https://www.ncbi.nlm.nih.gov/pubmed/10359391

Dihydroandrostenedione (Androstanedione) is a steroid metabolite and a precursor of both testosterone and estrone normally produced by the adrenal gland and gonads and is converted to testosterone through the action of 17β-hydroxysteroid dehydrogenase, which is found in most body tissues. Androstenedione is also produced by some plants and has recently been marketed as a product for increasing blood testosterone concentrations to be used as a natural alternative to anabolic steroid use. However, androstenedione administration during resistance training did not significantly alter the serum testosterone concentration in normotestosterogenic young men. The increased muscle size and strength observed with resistance training were also not augmented with androstenedione administration. The use of androstenedione increased the serum concentrations of estradiol and estrone, suggesting an increased aromatization of the ingested androstenedione and/or testosterone derived from the exogenous androstenedione. The use of androstenedione was associated with decreased levels of HDL-C. These data provide evidence that androstenedione does not enhance adaptations to resistance training and may result in potentially serious adverse health consequences in young men.

Originator

Sources: Z. physiol. Chem. (1934), 229, 185-91.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
20 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
PubMed

PubMed

TitleDatePubMed
Sleep deprivation and adaptive hormonal responses of healthy men.
1989
Synthesis of testosterone and 5alpha-androstanediols during nutritionally stimulated gonadal growth in Lytechinus variegatus lamarck (Echinodermata:Echinoidea).
1998 Aug
Androgen inactivation in human lung fibroblasts: variations in levels of 17 beta-hydroxysteroid dehydrogenase type 2 and 5 alpha-reductase activity compatible with androgen inactivation.
2002 Aug
An assessment of in vitro androgenic activity and the identification of environmental androgens in United Kingdom estuaries.
2002 Jul
Inclusion complexes of ketosteroids with beta-cyclodextrin.
2003 Apr
Effects of androgens on aromatase activity and 11C-vorozole binding in granulosa cells in vitro.
2003 Mar
13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands?
2003 Mar 28
5alpha-reduced C21 steroids are substrates for human cytochrome P450c17.
2003 Oct 15
Human liver S9 fractions: metabolism of dehydroepiandrosterone, epiandrosterone, and related 7-hydroxylated derivatives.
2005 Apr
5alpha-reductase in human embryonic kidney cell line HEK293: evidence for type II enzyme expression and activity.
2005 Feb
Inhibition of 3alpha-hydroxysteroid dehydrogenase (3alpha-HSD) activity of human lung microsomes by genistein, daidzein, coumestrol and C(18)-, C(19)- and C(21)-hydroxysteroids and ketosteroids.
2005 Jul
Characterization of 17alpha-hydroxysteroid dehydrogenase activity (17alpha-HSD) and its involvement in the biosynthesis of epitestosterone.
2005 Jul 14
Persistence and pathways of testosterone dissipation in agricultural soil.
2005 May-Jun
Androgen metabolism via 17beta-hydroxysteroid dehydrogenase type 3 in mammalian and non-mammalian vertebrates: comparison of the human and the zebrafish enzyme.
2005 Oct
Mechanism of proton transfer in the 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni.
2007 Nov 23
Proliferative effect of androst-4-ene-3,17-dione and its metabolites in the androgen-sensitive LNCaP cell line.
2008 Mar
Two homologous fungal carbonyl reductases with different substrate specificities.
2009 Mar 16
3-Ketosteroid 9alpha-hydroxylase is an essential factor in the pathogenesis of Mycobacterium tuberculosis.
2010 Jan
Patents

Patents

Sample Use Guides

During weeks 1, 2, 4, 5, 7, and 8, the men were randomized to either androstenedione, 300 mg/d (n = 10), or placebo (n = 10).
Route of Administration: Oral
Ishikawacells were treated with increasing concentrations of A4 (Androstanedione) (0-1000 pmol) for 4 days. Cell proliferation was measured by the (4,5-dimethylthiaxol-2-yi)-2,5-diphenyltetraxolium bromide (MTT) assay. Apoptosis was analyzed through Annexin-V/propidium iodide (PI) staining and flow cytometry: 17β-hydroxy steroid dehydrogenase type 1 (17β-HSD1) and aromatase mRNA expression was measured by reverse transcription-polymerase chain reaction (RT-PCR). Western blotting was used to detect cell signaling expressions of Akt/MAPK. A4 treatment (1 nM) decreased cell proliferation and increased apoptosis, as demonstrated by MTT and flow cytometry or related gene expression. The cellular responses induced by A4 treatment were mediated by activation of the Akt and MAPK signaling pathway. Treatment had no effect on 17β-HSD1 and aromatase expression.
Substance Class Chemical
Created
by admin
on Sat Jun 26 04:26:21 UTC 2021
Edited
by admin
on Sat Jun 26 04:26:21 UTC 2021
Record UNII
2KR72RNR8Z
Record Status Validated (UNII)
Record Version
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Name Type Language
DIHYDROANDROSTENEDIONE
Common Name English
DIHYDRO-ANDROSTENEDIONE
Common Name English
ANDROSTANE-3,17-DIONE
Systematic Name English
5.ALPHA.-ANDROSTANEDIONE
Systematic Name English
5.ALPHA.-ANDROSTANE-3,17-DIONE
Systematic Name English
NSC-9897
Code English
ANDROSTANE-3,17-DIONE, (5.ALPHA.)-
Systematic Name English
ANDROSTANEDIONE
Systematic Name English
NSC-60796
Code English
5.ALPHA.-ANDROSTA-3,17-DIONE
Common Name English
Classification Tree Code System Code
DEA NO. 4000
Created by admin on Sat Jun 26 04:26:21 UTC 2021 , Edited by admin on Sat Jun 26 04:26:21 UTC 2021
NCI_THESAURUS C2289
Created by admin on Sat Jun 26 04:26:21 UTC 2021 , Edited by admin on Sat Jun 26 04:26:21 UTC 2021
CFR 21 CFR 862.1430
Created by admin on Sat Jun 26 04:26:21 UTC 2021 , Edited by admin on Sat Jun 26 04:26:21 UTC 2021
Code System Code Type Description
CAS
846-46-8
Created by admin on Sat Jun 26 04:26:21 UTC 2021 , Edited by admin on Sat Jun 26 04:26:21 UTC 2021
PRIMARY
EPA CompTox
846-46-8
Created by admin on Sat Jun 26 04:26:21 UTC 2021 , Edited by admin on Sat Jun 26 04:26:21 UTC 2021
PRIMARY
DRUG BANK
DB01561
Created by admin on Sat Jun 26 04:26:21 UTC 2021 , Edited by admin on Sat Jun 26 04:26:21 UTC 2021
PRIMARY
WIKIPEDIA
Androstanedione
Created by admin on Sat Jun 26 04:26:21 UTC 2021 , Edited by admin on Sat Jun 26 04:26:21 UTC 2021
PRIMARY
NCI_THESAURUS
C107155
Created by admin on Sat Jun 26 04:26:21 UTC 2021 , Edited by admin on Sat Jun 26 04:26:21 UTC 2021
PRIMARY NCIT
ECHA (EC/EINECS)
212-685-5
Created by admin on Sat Jun 26 04:26:21 UTC 2021 , Edited by admin on Sat Jun 26 04:26:21 UTC 2021
PRIMARY
PUBCHEM
222865
Created by admin on Sat Jun 26 04:26:21 UTC 2021 , Edited by admin on Sat Jun 26 04:26:21 UTC 2021
PRIMARY
FDA UNII
2KR72RNR8Z
Created by admin on Sat Jun 26 04:26:21 UTC 2021 , Edited by admin on Sat Jun 26 04:26:21 UTC 2021
PRIMARY
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