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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

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

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 290.4403
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

CNS Activity

Originator

Butenandt, Adolf|Hanisch, Günter
2
Sources: 10.1515/bchm2.1935.237.1-3.89

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
androgen receptor
3
Target ID: 1.05586152E8
Gene Symbol: AR
Activator
1447
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
Neumune

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Androstenediol administration after trauma-hemorrhage attenuates inflammatory response, reduces organ damage, and improves survival following sepsis.
2006-08
Modulation of neurosteroid production in human neuroblastoma cells by Alzheimer's disease key proteins.
2006-07
Acute resistance exercise does not change the hormonal response to sublingual androstenediol intake.
2006-07
Metabolism of steroid hormones by Taenia solium and Taenia crassiceps cysticerci.
2006-06
Sex steroid concentrations and localization of steroidogenic enzyme expression in free-ranging female northern fur seals (Callorhinus ursinus).
2006-06
Rat 3alpha-hydroxysteroid dehydrogenase: to oxidize or reduce, that is the question.
2006-04
Dehydroepiandrosterone and its metabolites: differential effects on androgen receptor trafficking and transcriptional activity.
2006-04
Arginine 276 controls the directional preference of AKR1C9 (rat liver 3alpha-hydroxysteroid dehydrogenase) in human embryonic kidney 293 cells.
2006-04
Phase I study of STX 64 (667 Coumate) in breast cancer patients: the first study of a steroid sulfatase inhibitor.
2006-03-01
Androstenediol analogs as ER-beta-selective SERMs.
2006-02-15
Circulating neuroactive C21- and C19-steroids in young men before and after ejaculation.
2006
Application of stable carbon isotope analysis to the detection of 17beta-estradiol administration to cattle.
2005-11-04
Sex steroid metabolism in human peripheral blood mononuclear cells changes with aging.
2005-11
Enzymic conversion of 3beta-hydroxy-5-ene-steroids and their sulfates to 3-oxo-4-ene-steroids for increasing sensitivity in LC-APCI-MS.
2005-09-15
Steroid signalling in the ovarian surface epithelium.
2005-09
Salutary effects of androstenediol on hepatic function after trauma-hemorrhage are mediated via peroxisome proliferators-activated receptor gamma.
2005-08
Androgens induce relaxation of contractile activity in pregnant human myometrium at term: a nongenomic action on L-type calcium channels.
2005-08
Serum concentrations of estrogens, sex hormone binding globulin, and androgens and risk of breast hyperplasia in postmenopausal women.
2005-07
The identification and simultaneous quantification of 7-hydroxylated metabolites of pregnenolone, dehydroepiandrosterone, 3beta,17beta-androstenediol, and testosterone in human serum using gas chromatography-mass spectrometry.
2005-07
Anti-inflammatory and immune regulatory properties of 5-androsten-3beta, 17beta-diol (HE2100), and synthetic analogue HE3204: implications for treatment of autoimmune diseases.
2005-06
Specific modulation of nongenomic androgen signaling in the ovary.
2005-05-03
Dehydroepiandrosterone (DHEA) modulates GHRH, somatostatin and angiotensin II action at the pituitary level.
2005-04
Steroid sulfatase: molecular biology, regulation, and inhibition.
2005-04
Binding of estrogenic compounds to recombinant estrogen receptor-alpha: application to environmental analysis.
2005-03
Mechanism of salutary effects of androstenediol on hepatic function after trauma-hemorrhage: role of endothelial and inducible nitric oxide synthase.
2005-02
Effects of whole-body gamma irradiation and 5-androstenediol administration on serum G-CSF.
2005
Androgen conversion in osteoarthritis and rheumatoid arthritis synoviocytes--androstenedione and testosterone inhibit estrogen formation and favor production of more potent 5alpha-reduced androgens.
2005
C(19)-5-ene steroids in nature.
2005
Molecular specificity of 5-androstenediol as a systemic radioprotectant in mice.
2005
Effect of estrogen receptor agonists treatment in MPTP mice: evidence of neuroprotection by an ER alpha agonist.
2004-12
HPLC-RIA analysis of steroid hormone profile in a virilizing stromal tumor of the ovary.
2004-10-29
Serum concentrations of androstenediol and androstenediol sulfate, and their relation to cytokine production during and after normal pregnancy.
2004-09
Synthesis of 3-methyl-3-hydroxy-6-oxo-androstane derivatives.
2004-09
Partial agonist/antagonist properties of androstenedione and 4-androsten-3beta,17beta-diol.
2004-08
Anabolic-androgenic steroids and testosterone precursors: ergogenic aids and sport.
2004-08
Salutary effects of androstenediol on cardiac function and splanchnic perfusion after trauma-hemorrhage.
2004-08
Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements.
2004-07
Virilization of young children after topical androgen use by their parents.
2004-07
Expression of cytochrome P450c17 and other steroid-converting enzymes in the rat kidney throughout the life-span.
2004-06
Lack of defects in androgen production in children with hypospadias.
2004-06
Amelioration of murine antigen-induced arthritis by dehydroepiandrosterone (DHEA).
2004-05
Plasma lipoprotein profile in the male cynomolgus monkey under normal, hypogonadal, and combined androgen blockade conditions.
2004-04
Analysis of the nutritional supplement 1AD, its metabolites, and related endogenous hormones in biological matrices using liquid chromatography-tandem mass spectrometry.
2004-02-28
The adrenal androgen androstenediol is present in prostate cancer tissue after androgen deprivation therapy and activates mutated androgen receptor.
2004-01-15
Postmenopausal levels of oestrogen, androgen, and SHBG and breast cancer: long-term results of a prospective study.
2004-01-12
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.
2004-01
Metabolic inactivation of estrogens in breast tissue by UDP-glucuronosyltransferase enzymes: an overview.
2004
Adrenal steroid hormones and metaphyseal bone in children.
2004
Sex steroid hormones differentially regulate nitric oxide synthase and arginase activities in the proximal and distal rabbit vagina.
2003-12
The Safety and Efficacy of Anabolic Steroid Precursors: What is the Scientific Evidence?
2002-07
Patents

Patents

04891367
3
08361996
2
20010012630
2

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
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:34:56 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:56 GMT 2025
Record UNII
95PS51EMXY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANDROSTENEDIOL
JAN   MART.   MI   WHO-DD  
Systematic Name English
NEUMUNE
Preferred 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
Classification Tree Code System Code
NCI_THESAURUS C2360
Created by admin on Mon Mar 31 17:34:56 GMT 2025 , Edited by admin on Mon Mar 31 17:34:56 GMT 2025
LOINC 55851-0
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LOINC 25314-6
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LOINC 34238-6
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DEA NO. 4000
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LOINC 34237-8
Created by admin on Mon Mar 31 17:34:56 GMT 2025 , Edited by admin on Mon Mar 31 17:34:56 GMT 2025
LOINC 56033-4
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LOINC 34236-0
Created by admin on Mon Mar 31 17:34:56 GMT 2025 , Edited by admin on Mon Mar 31 17:34:56 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C95979
Created by admin on Mon Mar 31 17:34:56 GMT 2025 , Edited by admin on Mon Mar 31 17:34:56 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-306-8
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PRIMARY
FDA UNII
95PS51EMXY
Created by admin on Mon Mar 31 17:34:56 GMT 2025 , Edited by admin on Mon Mar 31 17:34:56 GMT 2025
PRIMARY
CAS
521-17-5
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PRIMARY
DRUG CENTRAL
214
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PRIMARY
WIKIPEDIA
Androstenediol
Created by admin on Mon Mar 31 17:34:56 GMT 2025 , Edited by admin on Mon Mar 31 17:34:56 GMT 2025
PRIMARY
NSC
12163
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PRIMARY
CHEBI
2710
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PRIMARY
EPA CompTox
DTXSID9022609
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PRIMARY
MESH
D015114
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PRIMARY
ChEMBL
CHEMBL440283
Created by admin on Mon Mar 31 17:34:56 GMT 2025 , Edited by admin on Mon Mar 31 17:34:56 GMT 2025
PRIMARY
MERCK INDEX
m1900
Created by admin on Mon Mar 31 17:34:56 GMT 2025 , Edited by admin on Mon Mar 31 17:34:56 GMT 2025
PRIMARY Merck Index
SMS_ID
100000077399
Created by admin on Mon Mar 31 17:34:56 GMT 2025 , Edited by admin on Mon Mar 31 17:34:56 GMT 2025
PRIMARY
EVMPD
SUB12899MIG
Created by admin on Mon Mar 31 17:34:56 GMT 2025 , Edited by admin on Mon Mar 31 17:34:56 GMT 2025
PRIMARY
PUBCHEM
10634
Created by admin on Mon Mar 31 17:34:56 GMT 2025 , Edited by admin on Mon Mar 31 17:34:56 GMT 2025
PRIMARY
DRUG BANK
DB01524
Created by admin on Mon Mar 31 17:34:56 GMT 2025 , Edited by admin on Mon Mar 31 17:34:56 GMT 2025
PRIMARY
Related Record Type Details
Structure of PRASTERONE
PARENT -> METABOLITE
IN VITRO
Related Record Type Details
Structure of ANDROSTENEDIOL
ACTIVE MOIETY
NIH
NCATS
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