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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 EPIANDROSTERONE

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])C[C@@H](O)CC[C@]34C

InChI

InChIKey=QGXBDMJGAMFCBF-LUJOEAJASA-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/h12-16,20H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,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 https://www.ncbi.nlm.nih.gov/pubmed/7726568 | https://www.ncbi.nlm.nih.gov/pubmed/12054855 | https://www.ncbi.nlm.nih.gov/pubmed/15650074 | https://www.ncbi.nlm.nih.gov/pubmed/17017935

The 17-ketosteroid epiandrosterone is a metabolite of testosterone precursor dehydroepiandrosterone (DHEA). Epiandrosterone have been considered to be merely inactive end product of DHEA, but may in fact be physiological effectors in their own right. It is formed in peripheral tissues, from which it is released into the circulation and is ultimately excreted in the urine. Epiandrosterone is only a weak androgen, but it is widely recognized to inhibit the pentose phosphate pathway and to decrease intracellular NADPH levels. Epiandrosterone may act as a L-type Ca2+ channel antagonist. Epiandrosterone mainly transformed into 17beta-hydroxylated derivatives, 7- or 16alpha-hydroxylated metabolites under NAD(P)H conditions, and 5alpha-androstane-3,17-dione under NAD(P)+ conditions. Epiandrosterone is used as an anabolic agent (dietary supplement, a precursor to dihydrotestosterone) to increase strength, muscle hardness and also improves libido.

CNS Activity

CNS Penetrant
2554
Curator's Comment: Androsterone injections increased brain levels of epiandrosterone in rats. No human data available.

Originator

Friedrich, A.|Butenandt, J.|Tscherning, K.
1
Sources: Drugs in Sport: Medicine, Healthcare. CTI Reviews, Cram101 Textbook Reviews, 2016. pp 275. ISBN 1490287876, 9781490287874

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Expression and characterization of the human 3 beta-hydroxysteroid sulfotransferases (SULT2B1a and SULT2B1b).
2001 Jun
Use of bioconversion for the preparation of [4-14C]-labeled 7 alpha- and 7 beta-hydroxylated derivatives of dehydroepiandrosterone and epiandrosterone.
2002 Dec
Epiandrosterone, a metabolite of testosterone precursor, blocks L-type calcium channels of ventricular myocytes and inhibits myocardial contractility.
2002 Jun
Pentose phosphate pathway coordinates multiple redox-controlled relaxing mechanisms in bovine coronary arteries.
2003 Dec
A facile and high yielding synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide--an internal standard in dope.
2003 Jan
Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines.
2003 Jan
7-Hydroxylated epiandrosterone (7-OH-EPIA) reduces ischaemia-induced neuronal damage both in vivo and in vitro.
2003 Jul
The human cytochrome P4507B1: catalytic activity studies.
2004 Dec
In vitro metabolism of dehydroepiandrosterone and testosterone by canine hair follicle cells.
2004 Feb
Protection against inflammatory neurodegeneration and glial cell death by 7beta-hydroxy epiandrosterone, a novel neurosteroid.
2004 Mar
Steroidogenic activities in MA-10 Leydig cells are differentially altered by cAMP and Müllerian inhibiting substance.
2004 Oct
Neurosteroids: metabolism in human intestine microsomes.
2005 Apr
Human liver S9 fractions: metabolism of dehydroepiandrosterone, epiandrosterone, and related 7-hydroxylated derivatives.
2005 Apr
Glucuronidation of steroidal alcohols using iodosugar and imidate donors.
2005 Apr 21
Role of pentose phosphate pathway-derived NADPH in hypoxic pulmonary vasoconstriction.
2006
Steroid hormone related male biased parasitism in chamois, Rupicapra rupicapra rupicapra.
2006 Jun 15
An open label, dose response study to determine the effect of a dietary supplement on dihydrotestosterone, testosterone and estradiol levels in healthy males.
2008 Aug 12
Isolation and identification of diglucuronides of some endogenous steroids in dogs.
2008 Feb
7beta-Hydroxy-epiandrosterone-mediated regulation of the prostaglandin synthesis pathway in human peripheral blood monocytes.
2008 Oct
Diagnosis of diseases of steroid hormone production, metabolism and action.
2009
Anabolic utilization of steroid hormones in Helicobacter pylori.
2009 Aug
Preferential utilization of NADPH as the endogenous electron donor for NAD(P)H:quinone oxidoreductase 1 (NQO1) in intact pulmonary arterial endothelial cells.
2009 Jan 1
A review of the current treatment methods for posthaemorrhagic hydrocephalus of infants.
2009 Jan 30
Inhibition of Lassa virus glycoprotein cleavage and multicycle replication by site 1 protease-adapted alpha(1)-antitrypsin variants.
2009 Jun 2
Epimerase activity of the human 11beta-hydroxysteroid dehydrogenase type 1 on 7-hydroxylated C19-steroids.
2009 Mar
Effects of valproate and carbamazepine monotherapy on neuroactive steroids, their precursors and metabolites in adult men with epilepsy.
2010 Oct
Patents

Patents

04181669
1
05486603
6
08623849
1
08653054
1
JP2002537317A
97
JP4849478B2
8

Sample Use Guides

In Vivo Use Guide
Epiandrosterone is used as an anabolic agent (dietary supplement). Recommended dosing is 300-400 mg for a 6-8 week cycle.
Route of Administration: Oral
In Vitro Use Guide
Epiandrosterone (1-500 uM) elicited dose-dependent relaxation in chemically contracted endothelium-removed bovine coronary arteries
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:19:53 UTC 2023
Edited
by admin
on Fri Dec 15 15:19:53 UTC 2023
Record UNII
8TR252Z538
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPIANDROSTERONE
MI  
Common Name English
NSC-93996
Code English
EPIANDROSTERONE [MI]
Common Name English
ANDROSTERONE, TRANS-
Common Name English
ISOANDROSTERONE
Common Name English
3.BETA.-HYDROXY-5.ALPHA.-ANDROSTAN-17-ONE
Systematic Name English
Classification Tree Code System Code
LOINC 2229-3
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
CFR 21 CFR 862.1430
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
DSLD 2986 (Number of products:14)
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
NCI_THESAURUS C243
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
WIKIPEDIA Designer-drugs-Epiandrosterone
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
Code System Code Type Description
PUBCHEM
441302
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-563-3
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
PRIMARY
NCI_THESAURUS
C61747
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
PRIMARY
CHEBI
541975
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
PRIMARY
CAS
481-29-8
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
PRIMARY
EPA CompTox
DTXSID20289698
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
PRIMARY
MERCK INDEX
m4934
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
PRIMARY Merck Index
NSC
93996
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
PRIMARY
WIKIPEDIA
EPIANDROSTERONE
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
PRIMARY
FDA UNII
8TR252Z538
Created by admin on Fri Dec 15 15:19:53 UTC 2023 , Edited by admin on Fri Dec 15 15:19:53 UTC 2023
PRIMARY
Related Record Type Details
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Structure of ANDROSTANE-3,7,17-TRIOL, (3BETA,5ALPHA,7BETA,17BETA)-
METABOLITE -> PARENT
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Structure of 7.BETA.-HYDROXY-EPI-ANDROSTERONE
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Structure of 3.BETA.-HYDROXY-5.ALPHA.-ANDROSTANE-7,17-DIONE
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IN VITRO
Structure of 16.ALPHA.-HYDROXYEPIANDROSTERONE
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Structure of 7.ALPHA.-HYDROXY-EPI-ANDROSTERONE
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Structure of 3.BETA.-ANDROSTANEDIOL
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