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 |
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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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Effect of oral androstenedione on serum testosterone and adaptations to resistance training in young men: a randomized controlled trial. | 1999 Jun 2 |
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Estrogen activation of the nuclear orphan receptor CAR (constitutive active receptor) in induction of the mouse Cyp2b10 gene. | 2000 Nov |
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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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Differential age-related changes of hypothalamus - pituitary - adrenal axis hormones in healthy women and men - role of interleukin 6. | 2001 |
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Secretion from neuropeptide-treated splenocytes modifies ovarian steroidogenesis. | 2001 |
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Aromatase inhibition reduces specifically one display of the ring dove courtship behavior. | 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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Novel assay for determination of androgen bioactivity in human serum. | 2001 Apr |
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Serum and follicular fluid hormone levels during in vitro fertilization after short- or long-course treatment with a gonadotropin-releasing hormone agonist. | 2001 Apr |
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Dynamics of the development of multiple follicles during ovarian stimulation for in vitro fertilization using recombinant follicle-stimulating hormone (Puregon) and various doses of the gonadotropin-releasing hormone antagonist ganirelix (Orgalutran/Antagon). | 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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The role of glutathione in the isomerization of delta 5-androstene-3,17-dione catalyzed by human glutathione transferase A1-1. | 2001 Apr 13 |
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Estrogen and androgen influence hypothalamic AVP and CRF concentrations in fetal and adult sheep. | 2001 Apr 2 |
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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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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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Androgen deficiency in women with hypopituitarism. | 2001 Feb |
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Bioavailable estradiol may be an important determinant of osteoporosis in men: the MINOS study. | 2001 Jan |
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Disruption of the joint synchrony of luteinizing hormone, testosterone, and androstenedione secretion in adolescents with polycystic ovarian syndrome. | 2001 Jan |
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Sertoli-Leydig cell tumor. | 2001 Jan |
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Establishment and characterization of a steroidogenic human granulosa-like tumor cell line, KGN, that expresses functional follicle-stimulating hormone receptor. | 2001 Jan |
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Lysyl oxidase and MMP-2 expression in dehydroepiandrosterone-induced polycystic ovary in rats. | 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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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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Reproductive effects of valproate, carbamazepine, and oxcarbazepine in men with epilepsy. | 2001 Jan 9 |
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Influence of endogenous androgens on carotid wall in postmenopausal women. | 2001 Jan-Feb |
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Detection and determination of anabolic steroids in nutritional supplements. | 2001 Jul |
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Gonadotropins at menopause: the influence of obesity, insulin resistance, and estrogens. | 2001 Jul |
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Aromatase inhibition by an 11,13-dihydroderivative of a sesquiterpene lactone. | 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 |
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Sex hormone-binding globulin as a marker of the effect of hormonal treatment in Turner's syndrome. | 2001 Mar |
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Follicle-stimulating hormone regulates steroidogenic enzymes in cultured cells of the chick embryo ovary. | 2001 Mar |
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Ergogenic aids: counseling the athlete. | 2001 Mar 1 |
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Effect of beta-estradiol on voltage-gated Ca(2+) channels in rat hippocampal neurons: a comparison with dehydroepiandrosterone. | 2001 Mar 30 |
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Adrenal steroids in human prostatic cancer cell lines. | 2001 Mar-Apr |
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Sebocytes are the key regulators of androgen homeostasis in human skin. | 2001 May |
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Regulation of glucocorticoid receptor alpha and beta isoforms and type I 11beta-hydroxysteroid dehydrogenase expression in human skeletal muscle cells: a key role in the pathogenesis of insulin resistance? | 2001 May |
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Over-the-counter drug use in gymnasiums: an underrecognized substance abuse problem? | 2001 May-Jun |
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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35190-8
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DB01536
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100000077419
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SUB12900MIG
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ACTIVE MOIETY
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