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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H30O2
Molecular Weight 290.4403
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANDROSTENEDIOL

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC=C4C[C@@H](O)CC[C@]34C

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
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
Non-steroidal and steroidal sulfamates: new drugs for cancer therapy.
2001 Jan 22
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
Influence of estrogens on the androgen metabolism in different subunits of human hair follicles.
2001 May-Jun
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
In vivo radioprotection by 5-androstenediol: stimulation of the innate immune system.
2001 Sep
Dehydroepiandrosterone (DHEA) stimulates neurogenesis in the hippocampus of the rat, promotes survival of newly formed neurons and prevents corticosterone-induced suppression.
2002 Aug
Dehydroepiandrosterone (DHEA) metabolism in Saccharomyces cerevisiae expressing mammalian steroid hydroxylase CYP7B: Ayr1p and Fox2p display 17beta-hydroxysteroid dehydrogenase activity.
2002 Jul
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
Oral andro-related prohormone supplementation: do the potential risks outweigh the benefits?
2003 Feb
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
Steroid sulphatase inhibitors for breast cancer therapy.
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
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
Virilization of young children after topical androgen use by their parents.
2004 Jul
Effects of whole-body gamma irradiation and 5-androstenediol administration on serum G-CSF.
2005
C(19)-5-ene steroids in nature.
2005
Mechanism of salutary effects of androstenediol on hepatic function after trauma-hemorrhage: role of endothelial and inducible nitric oxide synthase.
2005 Feb
Application of stable carbon isotope analysis to the detection of 17beta-estradiol administration to cattle.
2005 Nov 4
Circulating neuroactive C21- and C19-steroids in young men before and after ejaculation.
2006
Arginine 276 controls the directional preference of AKR1C9 (rat liver 3alpha-hydroxysteroid dehydrogenase) in human embryonic kidney 293 cells.
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
Metabolism of steroid hormones by Taenia solium and Taenia crassiceps cysticerci.
2006 Jun
Sex steroid concentrations and localization of steroidogenic enzyme expression in free-ranging female northern fur seals (Callorhinus ursinus).
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
HE2100
Code English
ANDROSTENEDIOL [JAN]
Common Name English
ANDROSTENEDIOL [MI]
Common Name English
HE-2100
Code English
NSC-12163
Code English
5-ANDENDIOL
Common Name English
Androstenediol [WHO-DD]
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
NEUMUNE
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C2360
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
LOINC 55851-0
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
LOINC 25314-6
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LOINC 34238-6
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DEA NO. 4000
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
LOINC 34237-8
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
LOINC 56033-4
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
LOINC 34236-0
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C95979
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-306-8
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
FDA UNII
95PS51EMXY
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
CAS
521-17-5
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PRIMARY
DRUG CENTRAL
214
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WIKIPEDIA
Androstenediol
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
NSC
12163
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
CHEBI
2710
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
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EPA CompTox
DTXSID9022609
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MESH
D015114
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL440283
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
MERCK INDEX
m1900
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY Merck Index
SMS_ID
100000077399
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
EVMPD
SUB12899MIG
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
PUBCHEM
10634
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
DRUG BANK
DB01524
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY