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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

Description
Curator's Comment:: description was created based on several sources, including: http://www.drugbank.ca/drugs/DB01524 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: 1.05586152E8
Gene Symbol: AR
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Neumune

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Sport nutritional supplements: quality and doping controls.
2001
Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group.
2001 Jul-Aug
Hormonal steroidogenesis in liver and small intestine of the green frog, Rana esculenta L.
2001 Nov 2
Endocrine and lipid responses to chronic androstenediol-herbal supplementation in 30 to 58 year old men.
2001 Oct
[Urinary nandrolone metabolites in antidoping control].
2001 Sep
Cytopathological changes in early stages of benign prostatic hyperplasia upon exposure to sustained delivery of androgens.
2002
The role of cytokines in regulating estrogen synthesis: implications for the etiology of breast cancer.
2002
Human nutritional supplements in the horse: comparative effects of 19-norandrostenedione and 19-norandrostenediol on the 19-norsteroid profile and consequences for doping control.
2002 Jan 25
Dehydroepiandrosterone (DHEA) metabolism in Saccharomyces cerevisiae expressing mammalian steroid hydroxylase CYP7B: Ayr1p and Fox2p display 17beta-hydroxysteroid dehydrogenase activity.
2002 Jul
Aromatase overexpression enhances the stimulatory effects of adrenal androgens on MCF7 breast cancer cells.
2002 Jul 31
Identification of dehydroepiandrosterone metabolites formed from human prostate homogenate using liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry.
2002 Jun 28
Induction of CYP3A expression by dehydroepiandrosterone: involvement of the pregnane X receptor.
2002 May
Radioprotective efficacy and acute toxicity of 5-androstenediol after subcutaneous or oral administration in mice.
2002 Nov
Steroid and sterol 7-hydroxylation: ancient pathways.
2002 Nov
Sex steroid hormones differentially regulate nitric oxide synthase and arginase activities in the proximal and distal rabbit vagina.
2003 Dec
Sterol structure and sphingomyelin acyl chain length modulate lateral packing elasticity and detergent solubility in model membranes.
2003 Dec
Oral andro-related prohormone supplementation: do the potential risks outweigh the benefits?
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
Asynchronous bilateral achilles tendon ruptures and androstenediol use.
2003 Nov-Dec
Simultaneous determination of androstenediol 3-sulfate and dehydroepiandrosterone sulfate in human serum using isotope diluted liquid chromatography-electrospray ionization-mass spectrometry.
2003 Oct 25
Steroid sulphatase inhibitors for breast cancer therapy.
2003 Sep
Adrenal steroid hormones and metaphyseal bone in children.
2004
Plasma lipoprotein profile in the male cynomolgus monkey under normal, hypogonadal, and combined androgen blockade conditions.
2004 Apr
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
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
Virilization of young children after topical androgen use by their parents.
2004 Jul
Expression of cytochrome P450c17 and other steroid-converting enzymes in the rat kidney throughout the life-span.
2004 Jun
Lack of defects in androgen production in children with hypospadias.
2004 Jun
Amelioration of murine antigen-induced arthritis by dehydroepiandrosterone (DHEA).
2004 May
Androgen conversion in osteoarthritis and rheumatoid arthritis synoviocytes--androstenedione and testosterone inhibit estrogen formation and favor production of more potent 5alpha-reduced androgens.
2005
Molecular specificity of 5-androstenediol as a systemic radioprotectant in mice.
2005
Dehydroepiandrosterone (DHEA) modulates GHRH, somatostatin and angiotensin II action at the pituitary level.
2005 Apr
Steroid sulfatase: molecular biology, regulation, and inhibition.
2005 Apr
Salutary effects of androstenediol on hepatic function after trauma-hemorrhage are mediated via peroxisome proliferators-activated receptor gamma.
2005 Aug
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
Application of stable carbon isotope analysis to the detection of 17beta-estradiol administration to cattle.
2005 Nov 4
Enzymic conversion of 3beta-hydroxy-5-ene-steroids and their sulfates to 3-oxo-4-ene-steroids for increasing sensitivity in LC-APCI-MS.
2005 Sep 15
Circulating neuroactive C21- and C19-steroids in young men before and after ejaculation.
2006
Androstenediol administration after trauma-hemorrhage attenuates inflammatory response, reduces organ damage, and improves survival following sepsis.
2006 Aug
Androstenediol analogs as ER-beta-selective SERMs.
2006 Feb 15
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
In Vitro Use Guide
Unknown
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