Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H26O2 |
Molecular Weight | 286.4085 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C
InChI
InChIKey=AEMFNILZOJDQLW-QAGGRKNESA-N
InChI=1S/C19H26O2/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
DescriptionSources: https://www.drugbank.ca/drugs/DB01536Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18203558 | https://www.ncbi.nlm.nih.gov/pubmed/8476772 | https://www.ncbi.nlm.nih.gov/pubmed/27558186
Sources: https://www.drugbank.ca/drugs/DB01536
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18203558 | https://www.ncbi.nlm.nih.gov/pubmed/8476772 | https://www.ncbi.nlm.nih.gov/pubmed/27558186
Androstenedione (Δ4-Androstenedione, 4-androstene-3,17-dione or 17-ketotestosterone) is an endogenous androgen steroid hormone and intermediate in the biosynthesis of testosterone from dehydroepiandrosterone (DHEA). In turn, Androstenedione is also a precursor of dihydrotestosterone (DHT), estrogens such as estradiol and estrone, and the neurosteroid 3α-androstanediol. Androstenedione is used to increase the production of the hormone testosterone to enhance athletic performance, increase energy, keep red blood cells healthy, enhance recovery and growth from exercise, and increase sexual desire and performance. Androstenedione has been shown to increase serum testosterone levels over an eight-hour period in men when taken as a single oral dose of 300 mg per day, but a dose of 100 mg had no significant effect on serum testosterone. However, serum levels of estradiol increased following both the 100 mg and 300 mg doses. The study also reported that the serum level of estrogens and testosterone produced varied widely among individuals. Androstenedione is currently used as a nutritional supplement to grow bigger muscles and stronger bones. This implies that androstenedione may have anabolic properties. Even though it has not been convincingly demonstrated yet that androstenedione is an anabolic steroid, its anabolic properties are likely based on its proven ability to increase testosterone levels. The role of testosterone in building stronger muscles and bones is widely accepted. Thus, high doses of testosterone-boosting drugs combined with strength training have been shown to increase muscle size and strength even in normal young men. This confirms what thousands of athletes who take anabolic steroids have known for decades. Yet androstenedione is different from testosterone-boosting drugs in a number of important aspects. To begin with, androstenedione is a naturally occurring substance that is produced by the body itself. In contrast to synthetic anabolic steroids, androstenedione is right at home in the human body, and perfectly complements the complex hormonal network in the body. Information about possible side effects and risks of androstenedione is very limited. Also, recent studies show that the drug's actions don't support manufacturer's claims. While a few individuals have shown increased levels of testosterone, most failed to achieve increases in blood testosterone levels. Initial medical research has raised concerns about this supplement's safety. Doctors worry that androstenedione may increase the risk of heart disease or liver cancer. In addition, research also associates androstenedione use with increases in estradiol, a female estrogen.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11806715 |
489.0 nM [IC50] | ||
Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22444875 |
30.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Morphometric analysis of cortical bone upon the exposure to sustained delivery of anabolic promoting agents using adult male rats as a model. | 2001 |
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Secretion from neuropeptide-treated splenocytes modifies ovarian steroidogenesis. | 2001 |
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Polycystic ovary syndrome: relationship between insulin sensitivity, sex hormone levels and ovarian stromal blood flow. | 2001 Apr |
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Pharmacokinetics and metabolism of formestane in breast cancer patients. | 2001 Apr |
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Sources of elevated serum androgens in postmenopausal women who develop breast cancer. | 2001 Apr |
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19-Oxygenation of C19-steroids with an A, B-ring enone structure, competitive inhibitors of estrogen biosynthesis, with human placental aromatase. | 2001 Apr |
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Apolipoprotein E is a putative autocrine regulator of the rat ovarian theca cell compartment. | 2001 Apr |
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Testicular development, histology, and hormone profiles in three yearling angus bulls with spermatogenic arrest. | 2001 Apr 15 |
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Leuprolide acetate treatment of adrenocortical disease in ferrets. | 2001 Apr 15 |
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Expression and localization of cytochrome P450 17 alpha-hydroxylase/c17,20-lyase in the avian brain. | 2001 Apr 27 |
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Metformin increases the ovulatory rate and pregnancy rate from clomiphene citrate in patients with polycystic ovary syndrome who are resistant to clomiphene citrate alone. | 2001 Feb |
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Effects of the anti-androgen finasteride on the modulatory actions of oestradiol on androgen metabolism by human gingival fibroblasts. | 2001 Feb |
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Androgens and the role of female "hyperaggressiveness" in spotted hyenas (Crocuta crocuta). | 2001 Feb |
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Substitution mutation C268Y causes 17 beta-hydroxysteroid dehydrogenase 3 deficiency. | 2001 Feb |
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Porcine gonadal and placental isozymes of aromatase cytochrome P450: sub-cellular distribution and support by NADPH-cytochrome P450 reductase. | 2001 Feb 14 |
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Changes in androgenic steroid profile due to urine contamination by microorganisms: a prospective study in the context of doping control. | 2001 Feb 15 |
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A strong association between biologically active testosterone and leptin in non-obese men and women is lost with increasing (central) adiposity. | 2001 Jan |
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Hydrocortisone suspension and hydrocortisone tablets are not bioequivalent in the treatment of children with congenital adrenal hyperplasia. | 2001 Jan |
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Differential regulation of inhibin B and inhibin a by follicle-stimulating hormone and local growth factors in human granulosa cells from small antral follicles. | 2001 Jan |
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High-impact loading training induces bone hyperresorption activity in young elite female gymnasts. | 2001 Jan |
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Human hepatocyte cell lines proliferating as cohesive spheroid colonies in alginate markedly upregulate both synthetic and detoxificatory liver function. | 2001 Jan |
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Sertoli-Leydig cell tumor. | 2001 Jan |
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Maternal steroids and contaminants in common tern eggs: a mechanism of endocrine disruption? | 2001 Jan |
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Effects of long-term alpha-tocopherol supplementation on serum hormones in older men. | 2001 Jan 1 |
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Steroidogenic response of adrenal tissues after administration of ACTH to dogs with hypercortisolemia. | 2001 Jan 15 |
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Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis. | 2001 Jan 22 |
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Expression of the 17beta-hydroxysteroid dehydrogenase type 5 mRNA in the human brain. | 2001 Jan 22 |
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Distribution of 17beta-hydroxysteroid dehydrogenases in human osteoblast-like cells. | 2001 Jan 22 |
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Inhibitors of type II 17beta-hydroxysteroid dehydrogenase. | 2001 Jan 22 |
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Pan1b (17betaHSD11)-enzymatic activity and distribution in the lung. | 2001 Jan 22 |
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Type 5 17beta-hydroxysteroid dehydrogenase: its role in the formation of androgens in women. | 2001 Jan 22 |
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Crucial role of cytokines in sex steroid formation in normal and tumoral tissues. | 2001 Jan 22 |
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Postmenopausal virilization, simple ovarian cyst, and hilus cell hyperplasia--is there an association? | 2001 Jan-Feb |
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Corticosteroid-induced inhibition of adrenal androgen production in selected patients with prostate cancer. | 2001 Jan-Feb |
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Gonadotropins at menopause: the influence of obesity, insulin resistance, and estrogens. | 2001 Jul |
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The impact of obesity and insulin resistance on the outcome of IVF or ICSI in women with polycystic ovarian syndrome. | 2001 Jun |
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Decline in circulating estradiol during the periovulatory period is correlated with decreases in estradiol and androgen, and in messenger RNA for p450 aromatase and p450 17alpha-hydroxylase, in bovine preovulatory follicles. | 2001 Jun |
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Aromatase inhibition by an 11,13-dihydroderivative of a sesquiterpene lactone. | 2001 Jun |
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Leukemia inhibitory factor antagonizes gonadotropin induced-testosterone synthesis in cultured porcine leydig cells: sites of action. | 2001 Jun |
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Biotransformation of cholesterol using Lactobacillus bulgaricus in a glucose-controlled bioreactor. | 2001 Jun |
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Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study. | 2001 Mar |
|
Congenital adrenal hyperplasia owing to 21-hydroxylase deficiency. Growth, development, and therapeutic considerations. | 2001 Mar |
|
Follicle-stimulating hormone regulates steroidogenic enzymes in cultured cells of the chick embryo ovary. | 2001 Mar |
|
Differential effects on the androgen status of postmenopausal women treated with tibolone and continuous combined estradiol and norethindrone acetate replacement therapy. | 2001 Mar |
|
Comparison of Diane 35 and Diane 35 plus finasteride in the treatment of hirsutism. | 2001 Mar |
|
Endogenous sex hormone levels in postmenopausal women with Alzheimer's disease. | 2001 Mar |
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Ergogenic aids: counseling the athlete. | 2001 Mar 1 |
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Dynamics of bioactive follicle-stimulating hormone secretion in women with polycystic ovary syndrome: effects of estradiol and progesterone. | 2001 May |
|
A conditional tetracycline-regulated increase in Gamma amino butyric acid production near luteinizing hormone-releasing hormone nerve terminals disrupts estrous cyclicity in the rat. | 2001 May |
|
Serum hormones and the alcohol-breast cancer association in postmenopausal women. | 2001 May 2 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27558186
In clinical study the experimental group consisted of 6 men (mean age±SE, 62.33±2.57) taking 300 mg of androstenedione supplement for 7 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8476772
Wild-type MCF-7 cell and MCF-7 cell sublines, one of which was stably transfected with the aromatase and neomycin resistance expression plasmids (MCF-7 CA) and the other only with the neomycin resistance expression plasmid (MCF-7 Cc) were used for activity evaluation. 300nM [3H]androstenedione is added to flasks containing cells seeded at 40,000 cells/cm 2 and the percent conversion to estrone and estradiol determined. A total of 106dpm/flask soo of 7alpha-[3H]androstenedione (NEN/Dupont, Boston, MA) was used as the substrate and 400 [3H]estrone and [3H]estradiol purified using thin layer chromatography. Results from the aromatase assays are expressed as pmol of estrogen (estrone and estradiol) formed per mg of DNA during either 1 or 3 days of incubation of substrate with cells.
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53343-0
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15028-4
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57
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1853-1
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53337-2
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21 CFR 862.1075
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53336-4
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1851-5
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9319-5
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4000
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72489-8
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53344-8
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1855-6
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C2360
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14603-5
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15027-6
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34240-2
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43817-6
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9310-4
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1854-9
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34239-4
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1852-3
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35190-8
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C244
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215
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1646010
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CHEMBL274826
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ANDROSTENEDIONE
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D000735
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200-554-5
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409J2J96VR
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63-05-8
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9563
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M1901
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784
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7335
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6128
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DTXSID8024523
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DB01536
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16422
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409J2J96VR
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SUB12900MIG
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ACTIVE MOIETY
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