Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H28O2 |
Molecular Weight | 288.4244 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])CC(=O)CC[C@]34C
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
DescriptionSources: https://www.drugbank.ca/drugs/DB01561Curator's Comment: The description was created based on several sources, including
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
Sources: https://www.drugbank.ca/drugs/DB01561
Curator's Comment: The description was created based on several sources, including
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3783591 |
20.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Synthesis of testosterone and 5alpha-androstanediols during nutritionally stimulated gonadal growth in Lytechinus variegatus lamarck (Echinodermata:Echinoidea). | 1998 Aug |
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Structure-function aspects and inhibitor design of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3). | 2001 Jan 22 |
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An assessment of in vitro androgenic activity and the identification of environmental androgens in United Kingdom estuaries. | 2002 Jul |
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Inclusion complexes of ketosteroids with beta-cyclodextrin. | 2003 Apr |
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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 |
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5alpha-reduced C21 steroids are substrates for human cytochrome P450c17. | 2003 Oct 15 |
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Human liver S9 fractions: metabolism of dehydroepiandrosterone, epiandrosterone, and related 7-hydroxylated derivatives. | 2005 Apr |
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5alpha-reductase in human embryonic kidney cell line HEK293: evidence for type II enzyme expression and activity. | 2005 Feb |
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Mechanistic roles of Ser-114, Tyr-155, and Lys-159 in 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni. | 2005 Feb 4 |
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Characterization of 17alpha-hydroxysteroid dehydrogenase activity (17alpha-HSD) and its involvement in the biosynthesis of epitestosterone. | 2005 Jul 14 |
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Androgen metabolism via 17beta-hydroxysteroid dehydrogenase type 3 in mammalian and non-mammalian vertebrates: comparison of the human and the zebrafish enzyme. | 2005 Oct |
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Two homologous fungal carbonyl reductases with different substrate specificities. | 2009 Mar 16 |
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Role of S114 in the NADH-induced conformational change and catalysis of 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni. | 2009 Oct |
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3-Ketosteroid 9alpha-hydroxylase is an essential factor in the pathogenesis of Mycobacterium tuberculosis. | 2010 Jan |
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Contributions of active site residues to cofactor binding and catalysis of 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase. | 2010 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10359391
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24169035
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.
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DEA NO. |
4000
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NCI_THESAURUS |
C2289
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CFR |
21 CFR 862.1430
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846-46-8
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9897
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15994
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60796
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DTXSID80233576
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DB01561
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Androstanedione
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C107155
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212-685-5
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22542
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222865
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2KR72RNR8Z
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ACTIVE MOIETY
PARENT (METABOLITE)