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
Molecular Formula | C19H28O2 |
Molecular Weight | 288.4244 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|
Synthesis of testosterone and 5alpha-androstanediols during nutritionally stimulated gonadal growth in Lytechinus variegatus lamarck (Echinodermata:Echinoidea). | 1998 Aug |
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Oxidative 3alpha-hydroxysteroid dehydrogenase activity of human type 10 17beta-hydroxysteroid dehydrogenase. | 2003 Nov |
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Metabolism of estrogens and androgens by scleractinian corals. | 2003 Nov |
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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 |
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Persistence and pathways of testosterone dissipation in agricultural soil. | 2005 May-Jun |
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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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Mechanism of proton transfer in the 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni. | 2007 Nov 23 |
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Proliferative effect of androst-4-ene-3,17-dione and its metabolites in the androgen-sensitive LNCaP cell line. | 2008 Mar |
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Two homologous fungal carbonyl reductases with different substrate specificities. | 2009 Mar 16 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:21:47 GMT 2023
by
admin
on
Fri Dec 15 15:21:47 GMT 2023
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Record UNII |
2KR72RNR8Z
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Record Status |
Validated (UNII)
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Record Version |
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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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IN VITRO
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ACTIVE MOIETY |