U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H26O2
Molecular Weight 286.4093
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANDROSTENEDIONE

SMILES

C[C@@]12CCC(=O)C=C2CC[C@@]3([H])[C@]4([H])CCC(=O)[C@@]4(C)CC[C@@]31[H]

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

Molecular Formula C19H26O2
Molecular Weight 286.4093
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Serum testosterone and sex hormone-binding globulin concentrations and the risk of prostate carcinoma: a longitudinal study.
1999 Jul 15
Effect of oral androstenedione on serum testosterone and adaptations to resistance training in young men: a randomized controlled trial.
1999 Jun 2
C-reactive protein in the hemolymph of Achatina fulica: interrelationship with sex steroids and metallothionein.
2000 Apr
Hormonal and seminal evaluation of Leydig cell tumour patients before and after orchiectomy.
2000 May
Estrogen activation of the nuclear orphan receptor CAR (constitutive active receptor) in induction of the mouse Cyp2b10 gene.
2000 Nov
Morphometric analysis of cortical bone upon the exposure to sustained delivery of anabolic promoting agents using adult male rats as a model.
2001
Effects of transdermal application of 7-oxo-DHEA on the levels of steroid hormones, gonadotropins and lipids in healthy men.
2001
Polycystic ovary syndrome: relationship between insulin sensitivity, sex hormone levels and ovarian stromal blood flow.
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
Troglitazone improves ovulation and hirsutism in the polycystic ovary syndrome: a multicenter, double blind, placebo-controlled trial.
2001 Apr
Novel assay for determination of androgen bioactivity in human serum.
2001 Apr
Candidate gene analysis in premature pubarche and adolescent hyperandrogenism.
2001 Apr
Serum and follicular fluid hormone levels during in vitro fertilization after short- or long-course treatment with a gonadotropin-releasing hormone agonist.
2001 Apr
Apolipoprotein E is a putative autocrine regulator of the rat ovarian theca cell compartment.
2001 Apr
The role of glutathione in the isomerization of delta 5-androstene-3,17-dione catalyzed by human glutathione transferase A1-1.
2001 Apr 13
Leuprolide acetate treatment of adrenocortical disease in ferrets.
2001 Apr 15
Estrogen and androgen influence hypothalamic AVP and CRF concentrations in fetal and adult sheep.
2001 Apr 2
Expression and localization of cytochrome P450 17 alpha-hydroxylase/c17,20-lyase in the avian brain.
2001 Apr 27
Androgen deficiency in women with hypopituitarism.
2001 Feb
Muting of androgen negative feedback unveils impoverished gonadotropin-releasing hormone/luteinizing hormone secretory reactivity in healthy older men.
2001 Feb
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol.
2001 Feb 28
Hydrocortisone suspension and hydrocortisone tablets are not bioequivalent in the treatment of children with congenital adrenal hyperplasia.
2001 Jan
Bioavailable estradiol may be an important determinant of osteoporosis in men: the MINOS study.
2001 Jan
Disruption of the joint synchrony of luteinizing hormone, testosterone, and androstenedione secretion in adolescents with polycystic ovarian syndrome.
2001 Jan
High-impact loading training induces bone hyperresorption activity in young elite female gymnasts.
2001 Jan
Effects of a new selective estrogen receptor modulator (MDL 103,323) on cancellous and cortical bone in ovariectomized ewes: a biochemical, histomorphometric, and densitometric study.
2001 Jan
Establishment and characterization of a steroidogenic human granulosa-like tumor cell line, KGN, that expresses functional follicle-stimulating hormone receptor.
2001 Jan
Lysyl oxidase and MMP-2 expression in dehydroepiandrosterone-induced polycystic ovary in rats.
2001 Jan
Effects of long-term alpha-tocopherol supplementation on serum hormones in older men.
2001 Jan 1
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase.
2001 Jan 22
Type 5 17beta-hydroxysteroid dehydrogenase: its role in the formation of androgens in women.
2001 Jan 22
Reproductive effects of valproate, carbamazepine, and oxcarbazepine in men with epilepsy.
2001 Jan 9
Postmenopausal virilization, simple ovarian cyst, and hilus cell hyperplasia--is there an association?
2001 Jan-Feb
Influence of endogenous androgens on carotid wall in postmenopausal women.
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
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
Assessment of endocrine status in patients undergoing in-vitro fertilization treatment. Is it necessary?
2001 Mar
Sex hormone-binding globulin as a marker of the effect of hormonal treatment in Turner's syndrome.
2001 Mar
Testosterone deficiency in women.
2001 Mar
Follicle-stimulating hormone regulates steroidogenic enzymes in cultured cells of the chick embryo ovary.
2001 Mar
Effect of beta-estradiol on voltage-gated Ca(2+) channels in rat hippocampal neurons: a comparison with dehydroepiandrosterone.
2001 Mar 30
Adrenal steroids in human prostatic cancer cell lines.
2001 Mar-Apr
Effects of thyroid hormones on bovine granulosa and thecal cell function in vitro: dependence on insulin and gonadotropins.
2001 May
Sebocytes are the key regulators of androgen homeostasis in human skin.
2001 May
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
Dynamics of bioactive follicle-stimulating hormone secretion in women with polycystic ovary syndrome: effects of estradiol and progesterone.
2001 May
Does obesity diminish the positive effect of oral contraceptive treatment on hyperandrogenism in women with polycystic ovarian syndrome?
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:34:58 UTC 2021
Edited
by admin
on Sat Jun 26 16:34:58 UTC 2021
Record UNII
409J2J96VR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANDROSTENEDIONE
HSDB   JAN   MART.   MI   VANDF   WHO-DD  
Systematic Name English
ANDROSTENEDIONE [MI]
Common Name English
ANDROSTENEDIONE [JAN]
Common Name English
ANDROSTENEDIONE [WHO-DD]
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
TESTOSTERONE IMPURITY A [EP]
Common Name English
4-ANDROSTENE-3,17-DIONE
Systematic Name English
NSC-9563
Code English
4-ANDROSTENEDIONE
Systematic Name English
ANDROSTENEDIONE [MART.]
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
Created by admin on Sat Jun 26 16:35:00 UTC 2021 , Edited by admin on Sat Jun 26 16:35:00 UTC 2021
PRIMARY
DRUG CENTRAL
215
Created by admin on Sat Jun 26 16:34:59 UTC 2021 , Edited by admin on Sat Jun 26 16:34:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL274826
Created by admin on Sat Jun 26 16:34:59 UTC 2021 , Edited by admin on Sat Jun 26 16:34:59 UTC 2021
PRIMARY
WIKIPEDIA
ANDROSTENEDIONE
Created by admin on Sat Jun 26 16:35:00 UTC 2021 , Edited by admin on Sat Jun 26 16:35:00 UTC 2021
PRIMARY
MESH
D000735
Created by admin on Sat Jun 26 16:35:00 UTC 2021 , Edited by admin on Sat Jun 26 16:35:00 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-554-5
Created by admin on Sat Jun 26 16:34:59 UTC 2021 , Edited by admin on Sat Jun 26 16:34:59 UTC 2021
PRIMARY
CAS
63-05-8
Created by admin on Sat Jun 26 16:34:59 UTC 2021 , Edited by admin on Sat Jun 26 16:34:59 UTC 2021
PRIMARY
USP_CATALOG
1646010
Created by admin on Sat Jun 26 16:35:00 UTC 2021 , Edited by admin on Sat Jun 26 16:35:00 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M1901
Created by admin on Sat Jun 26 16:35:00 UTC 2021 , Edited by admin on Sat Jun 26 16:35:00 UTC 2021
PRIMARY Merck Index
RXCUI
784
Created by admin on Sat Jun 26 16:35:00 UTC 2021 , Edited by admin on Sat Jun 26 16:35:00 UTC 2021
PRIMARY RxNorm
HSDB
7335
Created by admin on Sat Jun 26 16:34:59 UTC 2021 , Edited by admin on Sat Jun 26 16:34:59 UTC 2021
PRIMARY
PUBCHEM
6128
Created by admin on Sat Jun 26 16:35:00 UTC 2021 , Edited by admin on Sat Jun 26 16:35:00 UTC 2021
PRIMARY
EPA CompTox
63-05-8
Created by admin on Sat Jun 26 16:34:59 UTC 2021 , Edited by admin on Sat Jun 26 16:34:59 UTC 2021
PRIMARY
DRUG BANK
DB01536
Created by admin on Sat Jun 26 16:34:59 UTC 2021 , Edited by admin on Sat Jun 26 16:34:59 UTC 2021
PRIMARY
FDA UNII
409J2J96VR
Created by admin on Sat Jun 26 16:34:59 UTC 2021 , Edited by admin on Sat Jun 26 16:34:59 UTC 2021
PRIMARY
EVMPD
SUB12900MIG
Created by admin on Sat Jun 26 16:34:59 UTC 2021 , Edited by admin on Sat Jun 26 16:34:59 UTC 2021
PRIMARY
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