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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
Structure of ANDROSTENEDIONE

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

HIDE SMILES / InChI

Description
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.

Originator

Sources: Uber Androsteron, ein Krystallisiertes Mannliches Sexualhormon I. Isoliereng und Reindarstellung aus Mannerham. Butenandt, A., Tscherning, K. Z. Physiol. Chem. 229:167-184

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
489.0 nM [IC50]
30.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Morphometric analysis of cortical bone upon the exposure to sustained delivery of anabolic promoting agents using adult male rats as a model.
2001
Secretion from neuropeptide-treated splenocytes modifies ovarian steroidogenesis.
2001
Polycystic ovary syndrome: relationship between insulin sensitivity, sex hormone levels and ovarian stromal blood flow.
2001 Apr
Pharmacokinetics and metabolism of formestane in breast cancer patients.
2001 Apr
Sources of elevated serum androgens in postmenopausal women who develop breast cancer.
2001 Apr
19-Oxygenation of C19-steroids with an A, B-ring enone structure, competitive inhibitors of estrogen biosynthesis, with human placental aromatase.
2001 Apr
Apolipoprotein E is a putative autocrine regulator of the rat ovarian theca cell compartment.
2001 Apr
Testicular development, histology, and hormone profiles in three yearling angus bulls with spermatogenic arrest.
2001 Apr 15
Leuprolide acetate treatment of adrenocortical disease in ferrets.
2001 Apr 15
Expression and localization of cytochrome P450 17 alpha-hydroxylase/c17,20-lyase in the avian brain.
2001 Apr 27
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
Effects of the anti-androgen finasteride on the modulatory actions of oestradiol on androgen metabolism by human gingival fibroblasts.
2001 Feb
Androgens and the role of female "hyperaggressiveness" in spotted hyenas (Crocuta crocuta).
2001 Feb
Substitution mutation C268Y causes 17 beta-hydroxysteroid dehydrogenase 3 deficiency.
2001 Feb
Porcine gonadal and placental isozymes of aromatase cytochrome P450: sub-cellular distribution and support by NADPH-cytochrome P450 reductase.
2001 Feb 14
Changes in androgenic steroid profile due to urine contamination by microorganisms: a prospective study in the context of doping control.
2001 Feb 15
A strong association between biologically active testosterone and leptin in non-obese men and women is lost with increasing (central) adiposity.
2001 Jan
Hydrocortisone suspension and hydrocortisone tablets are not bioequivalent in the treatment of children with congenital adrenal hyperplasia.
2001 Jan
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
High-impact loading training induces bone hyperresorption activity in young elite female gymnasts.
2001 Jan
Human hepatocyte cell lines proliferating as cohesive spheroid colonies in alginate markedly upregulate both synthetic and detoxificatory liver function.
2001 Jan
Sertoli-Leydig cell tumor.
2001 Jan
Maternal steroids and contaminants in common tern eggs: a mechanism of endocrine disruption?
2001 Jan
Effects of long-term alpha-tocopherol supplementation on serum hormones in older men.
2001 Jan 1
Steroidogenic response of adrenal tissues after administration of ACTH to dogs with hypercortisolemia.
2001 Jan 15
Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis.
2001 Jan 22
Expression of the 17beta-hydroxysteroid dehydrogenase type 5 mRNA in the human brain.
2001 Jan 22
Distribution of 17beta-hydroxysteroid dehydrogenases in human osteoblast-like cells.
2001 Jan 22
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase.
2001 Jan 22
Pan1b (17betaHSD11)-enzymatic activity and distribution in the lung.
2001 Jan 22
Type 5 17beta-hydroxysteroid dehydrogenase: its role in the formation of androgens in women.
2001 Jan 22
Crucial role of cytokines in sex steroid formation in normal and tumoral tissues.
2001 Jan 22
Postmenopausal virilization, simple ovarian cyst, and hilus cell hyperplasia--is there an association?
2001 Jan-Feb
Corticosteroid-induced inhibition of adrenal androgen production in selected patients with prostate cancer.
2001 Jan-Feb
Gonadotropins at menopause: the influence of obesity, insulin resistance, and estrogens.
2001 Jul
The impact of obesity and insulin resistance on the outcome of IVF or ICSI in women with polycystic ovarian syndrome.
2001 Jun
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
Aromatase inhibition by an 11,13-dihydroderivative of a sesquiterpene lactone.
2001 Jun
Leukemia inhibitory factor antagonizes gonadotropin induced-testosterone synthesis in cultured porcine leydig cells: sites of action.
2001 Jun
Biotransformation of cholesterol using Lactobacillus bulgaricus in a glucose-controlled bioreactor.
2001 Jun
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
Ergogenic aids: counseling the athlete.
2001 Mar 1
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
Patents

Sample Use Guides

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
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.
Name Type Language
ANDROSTENEDIONE
HSDB   JAN   MART.   MI   VANDF   WHO-DD  
Systematic Name English
ANDROSTENEDIONE [MI]
Common Name English
ANDROSTENEDIONE [JAN]
Common Name English
TESTOSTERONE RELATED COMPOUND A [USP-RS]
Common Name English
4-ANDENDION
Common Name English
ANDROSTENEDIONE [VANDF]
Common Name English
ANDROSTENEDIONE [HSDB]
Common Name English
4-ANDROSTENE-3,17-DIONE
Systematic Name English
TESTOSTERONE IMPURITY A [EP IMPURITY]
Common Name English
NSC-9563
Code English
4-ANDROSTENEDIONE
Systematic Name English
ANDROSTENEDIONE [MART.]
Common Name English
Androstenedione [WHO-DD]
Common Name English
Classification Tree Code System Code
LOINC 53343-0
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LOINC 15028-4
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LIVERTOX 57
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LOINC 1853-1
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LOINC 53337-2
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CFR 21 CFR 862.1075
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LOINC 53336-4
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LOINC 1851-5
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LOINC 9319-5
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DEA NO. 4000
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LOINC 72489-8
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LOINC 53344-8
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LOINC 1855-6
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NCI_THESAURUS C2360
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LOINC 14603-5
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LOINC 15027-6
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LOINC 34240-2
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LOINC 43817-6
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LOINC 9310-4
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LOINC 1854-9
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LOINC 34239-4
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LOINC 1852-3
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LOINC 35190-8
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Code System Code Type Description
NCI_THESAURUS
C244
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PRIMARY
DRUG CENTRAL
215
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PRIMARY
RS_ITEM_NUM
1646010
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PRIMARY
ChEMBL
CHEMBL274826
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PRIMARY
WIKIPEDIA
ANDROSTENEDIONE
Created by admin on Fri Dec 16 15:57:25 UTC 2022 , Edited by admin on Fri Dec 16 15:57:25 UTC 2022
PRIMARY
MESH
D000735
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PRIMARY
ECHA (EC/EINECS)
200-554-5
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PRIMARY
DAILYMED
409J2J96VR
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PRIMARY
CAS
63-05-8
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PRIMARY
NSC
9563
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PRIMARY
MERCK INDEX
M1901
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PRIMARY Merck Index
RXCUI
784
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PRIMARY RxNorm
HSDB
7335
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PRIMARY
PUBCHEM
6128
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PRIMARY
EPA CompTox
DTXSID8024523
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PRIMARY
DRUG BANK
DB01536
Created by admin on Fri Dec 16 15:57:25 UTC 2022 , Edited by admin on Fri Dec 16 15:57:25 UTC 2022
PRIMARY
CHEBI
16422
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PRIMARY
FDA UNII
409J2J96VR
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PRIMARY
EVMPD
SUB12900MIG
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PRIMARY