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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H30O2
Molecular Weight 290.441
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANDROSTENEDIOL

SMILES

C[C@@]12CC[C@@]([H])(CC2=CC[C@@]3([H])[C@]4([H])CC[C@@]([H])([C@@]4(C)CC[C@@]31[H])O)O

InChI

InChIKey=QADHLRWLCPCEKT-LOVVWNRFSA-N
InChI=1S/C19H30O2/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/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H30O2
Molecular Weight 290.441
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: http://www.webmd.com/vitamins-supplements/ingredientmono-595-androstenediol.aspx?activeingredientid=595&activeingredientname=androstenediol

This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. The value of Δ5-diol as a radiation countermeasure is based mainly on its stimulation of production of white blood cells and platelets. Androstenediol used by the body to make testosterone and estrogen. There is some concern that androstenediol might increase the risk of coronary heart disease. There is also developing evidence that androstenediol might help prostate cancer cells grow. Taking androstenediol along with estrogen and testosterone pills might cause too much estrogen or testosterone in the body.

Originator

Sources: 10.1515/bchm2.1935.237.1-3.89

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: 105586155
Gene Symbol: AR
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Neumune
PubMed

PubMed

TitleDatePubMed
Effects of testosterone precursor supplementation on intensive weight training.
2001 Apr
cyp7b1 catalyses the 7alpha-hydroxylation of dehydroepiandrosterone and 25-hydroxycholesterol in rat prostate.
2001 Apr 15
In vivo protection against gamma-irradiation with 5-androstenediol.
2001 Jul
Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group.
2001 Jul-Aug
Serum concentration of androstenediol and androstenediol sulfate in patients with hyperthyroidism and hypothyroidism.
2001 Jun
Expression and characterization of the human 3 beta-hydroxysteroid sulfotransferases (SULT2B1a and SULT2B1b).
2001 Jun
Serum hormones and the alcohol-breast cancer association in postmenopausal women.
2001 May 2
In vivo radioprotection by 5-androstenediol: stimulation of the innate immune system.
2001 Sep
Effects of prohormone supplementation in humans: a review.
2002 Dec
Protection against gamma-irradiation with 5-androstenediol.
2002 Feb
Induction of CYP3A expression by dehydroepiandrosterone: involvement of the pregnane X receptor.
2002 May
Investigations into the biosynthetic pathways for classical and ring B-unsaturated oestrogens in equine placental preparations and allantochorionic tissues.
2002 Nov
Steroid and sterol 7-hydroxylation: ancient pathways.
2002 Nov
Immune up-regulation and tumor apoptosis by androstene steroids.
2002 Nov
Serum sex hormones and breast cancer risk factors in postmenopausal women.
2003 Apr
3Beta-sulfamate derivatives of C19 and C21 steroids bearing a t-butylbenzyl or a benzyl group: synthesis and evaluation as non-estrogenic and non-androgenic steroid sulfatase inhibitors.
2003 Feb
Characterisation of estrogenic 17beta-hydroxysteroid dehydrogenase (17beta-HSD) activity in the human brain.
2003 Jul
The effects of androstenediol and dehydroepiandrosterone on the immune response to BCG at puberty.
2003 Jun
The human kidney is a progesterone-metabolizing and androgen-producing organ.
2003 Jun
Chronic effects of dehydroepiandrosterone on rat adipose tissue metabolism.
2003 Mar
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
2003 Oct
Identification of 5alpha-androst-1-ene-3beta,17beta-diol in the fat of Sus scrofa L.: a "nutritional supplement" not found previously in the food supply.
2003 Sep
Partial agonist/antagonist properties of androstenedione and 4-androsten-3beta,17beta-diol.
2004 Aug
Anabolic-androgenic steroids and testosterone precursors: ergogenic aids and sport.
2004 Aug
Salutary effects of androstenediol on cardiac function and splanchnic perfusion after trauma-hemorrhage.
2004 Aug
Effect of estrogen receptor agonists treatment in MPTP mice: evidence of neuroprotection by an ER alpha agonist.
2004 Dec
The proliferative effects of 5-androstene-3 beta,17 beta-diol and 5 alpha-dihydrotestosterone on cell cycle analysis and cell proliferation in MCF7, T47D and MDAMB231 breast cancer cell lines.
2004 Jan
In vivo effects of an intrafollicular injection of insulin-like growth factor 1 on the mechanism of follicle deviation in heifers and mares.
2004 Jan
Analysis of the nutritional supplement 1AD, its metabolites, and related endogenous hormones in biological matrices using liquid chromatography-tandem mass spectrometry.
2004 Jan-Feb
Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements.
2004 Jul
Lack of defects in androgen production in children with hypospadias.
2004 Jun
Amelioration of murine antigen-induced arthritis by dehydroepiandrosterone (DHEA).
2004 May
Serum concentrations of androstenediol and androstenediol sulfate, and their relation to cytokine production during and after normal pregnancy.
2004 Sep
Synthesis of 3-methyl-3-hydroxy-6-oxo-androstane derivatives.
2004 Sep
C(19)-5-ene steroids in nature.
2005
Molecular specificity of 5-androstenediol as a systemic radioprotectant in mice.
2005
Androgens induce relaxation of contractile activity in pregnant human myometrium at term: a nongenomic action on L-type calcium channels.
2005 Aug
Anti-inflammatory and immune regulatory properties of 5-androsten-3beta, 17beta-diol (HE2100), and synthetic analogue HE3204: implications for treatment of autoimmune diseases.
2005 Jun
Binding of estrogenic compounds to recombinant estrogen receptor-alpha: application to environmental analysis.
2005 Mar
Specific modulation of nongenomic androgen signaling in the ovary.
2005 May-Jun
Steroid signalling in the ovarian surface epithelium.
2005 Sep
Dehydroepiandrosterone and its metabolites: differential effects on androgen receptor trafficking and transcriptional activity.
2006 Apr
Androstenediol administration after trauma-hemorrhage attenuates inflammatory response, reduces organ damage, and improves survival following sepsis.
2006 Aug
Modulation of neurosteroid production in human neuroblastoma cells by Alzheimer's disease key proteins.
2006 Jul
Acute resistance exercise does not change the hormonal response to sublingual androstenediol intake.
2006 Jul
Metabolism of steroid hormones by Taenia solium and Taenia crassiceps cysticerci.
2006 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: In Phase I human safety studies conducted in the U.S. and The Netherlands, as of December 2005, a total of 111 volunteers had been enrolled, with 39 volunteers having completed the 5-day treatment course.
The 200 mg dose given over 5 days may be effective as a radiation countermeasure for humans
Route of Administration: Intramuscular
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:15:58 UTC 2021
Edited
by admin
on Sat Jun 26 05:15:58 UTC 2021
Record UNII
95PS51EMXY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANDROSTENEDIOL
JAN   MART.   MI   WHO-DD  
Systematic Name English
ANDROSTENEDIOL [MART.]
Common Name English
5-ANDROSTENEDIOL
Systematic Name English
5-ANDROSTENE-3.BETA.,17.BETA.-DIOL
Systematic Name English
ANDROSTENEDIOL [JAN]
Common Name English
ANDROSTENEDIOL [MI]
Common Name English
NSC-12163
Code English
5-ANDENDIOL
Common Name English
(3.BETA.,17.BETA.)-ANDROST-5-ENE-3,17-DIOL
Systematic Name English
ANDROSTENEDIOL, (-)-
Systematic Name English
5-ANDROSTENE-3.BETA.O,17.BETA.-DIOL
Systematic Name English
ANDROSTENEDIOL [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2360
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
LOINC 55851-0
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
LOINC 25314-6
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
LOINC 34238-6
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
DEA NO. 4000
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
LOINC 34237-8
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
LOINC 56033-4
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
LOINC 34236-0
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C95979
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-306-8
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
PRIMARY
FDA UNII
95PS51EMXY
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
PRIMARY
CAS
521-17-5
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
PRIMARY
DRUG CENTRAL
214
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
PRIMARY
EPA CompTox
521-17-5
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
PRIMARY
MESH
D015114
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
PRIMARY
ChEMBL
CHEMBL440283
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
PRIMARY
MERCK INDEX
M1900
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
PRIMARY Merck Index
EVMPD
SUB12899MIG
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
PRIMARY
PUBCHEM
10634
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
PRIMARY
DRUG BANK
DB01524
Created by admin on Sat Jun 26 05:15:58 UTC 2021 , Edited by admin on Sat Jun 26 05:15:58 UTC 2021
PRIMARY
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IN VITRO
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ACTIVE MOIETY