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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 EPIANDROSTERONE

SMILES

C[C@@]12CC[C@@]([H])(C[C@]2([H])CC[C@@]3([H])[C@]4([H])CCC(=O)[C@@]4(C)CC[C@@]31[H])O

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

Description
Curator's Comment:: 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

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

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

Originator

Sources: Drugs in Sport: Medicine, Healthcare. CTI Reviews, Cram101 Textbook Reviews, 2016. pp 275. ISBN 1490287876, 9781490287874

Approval Year

Targets
PubMed

PubMed

TitleDatePubMed
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
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
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
Human liver S9 fractions: metabolism of dehydroepiandrosterone, epiandrosterone, and related 7-hydroxylated derivatives.
2005 Apr
Role of pentose phosphate pathway-derived NADPH in hypoxic pulmonary vasoconstriction.
2006
Hypoxia promotes relaxation of bovine coronary arteries through lowering cytosolic NADPH.
2006 Jun
Hexose-6-phosphate dehydrogenase modulates 11beta-hydroxysteroid dehydrogenase type 1-dependent metabolism of 7-keto- and 7beta-hydroxy-neurosteroids.
2007 Jun 27
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
Diagnosis of diseases of steroid hormone production, metabolism and action.
2009
Parameters for ultra-performance liquid chromatographic/tandem mass spectrometric analysis of selected androgens versus estrogens in aqueous matrices.
2009 Aug 15
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
Analysis of conjugated steroid androgens: deconjugation, derivatisation and associated issues.
2009 Jul 12
Inhibition of Trypanosoma brucei glucose-6-phosphate dehydrogenase by human steroids and their effects on the viability of cultured parasites.
2009 Mar 15
In vitro antiviral activity of dehydroepiandrosterone and its synthetic derivatives against vesicular stomatitis virus.
2009 Nov
16-bromoepiandrosterone, an activator of the mammalian immune system, inhibits glucose 6-phosphate dehydrogenase from Trypanosoma cruzi and is toxic to these parasites grown in culture.
2010 Jul 1
Determination of (13)C/(12)C ratios of endogenous urinary steroids excreted as sulpho conjugates.
2010 Nov 15
Effects of valproate and carbamazepine monotherapy on neuroactive steroids, their precursors and metabolites in adult men with epilepsy.
2010 Oct
Patents

Sample Use Guides

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
Epiandrosterone (1-500 uM) elicited dose-dependent relaxation in chemically contracted endothelium-removed bovine coronary arteries
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:02:59 UTC 2021
Edited
by admin
on Sat Jun 26 05:02:59 UTC 2021
Record UNII
8TR252Z538
Record Status Validated (UNII)
Record Version
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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 Sat Jun 26 05:02:59 UTC 2021 , Edited by admin on Sat Jun 26 05:02:59 UTC 2021
CFR 21 CFR 862.1430
Created by admin on Sat Jun 26 05:02:59 UTC 2021 , Edited by admin on Sat Jun 26 05:02:59 UTC 2021
DSLD 2986 (Number of products:14)
Created by admin on Sat Jun 26 05:02:59 UTC 2021 , Edited by admin on Sat Jun 26 05:02:59 UTC 2021
NCI_THESAURUS C243
Created by admin on Sat Jun 26 05:02:59 UTC 2021 , Edited by admin on Sat Jun 26 05:02:59 UTC 2021
Code System Code Type Description
PUBCHEM
441302
Created by admin on Sat Jun 26 05:02:59 UTC 2021 , Edited by admin on Sat Jun 26 05:02:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-563-3
Created by admin on Sat Jun 26 05:02:59 UTC 2021 , Edited by admin on Sat Jun 26 05:02:59 UTC 2021
PRIMARY
NCI_THESAURUS
C61747
Created by admin on Sat Jun 26 05:02:59 UTC 2021 , Edited by admin on Sat Jun 26 05:02:59 UTC 2021
PRIMARY
CAS
481-29-8
Created by admin on Sat Jun 26 05:02:59 UTC 2021 , Edited by admin on Sat Jun 26 05:02:59 UTC 2021
PRIMARY
MERCK INDEX
M4934
Created by admin on Sat Jun 26 05:02:59 UTC 2021 , Edited by admin on Sat Jun 26 05:02:59 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
EPIANDROSTERONE
Created by admin on Sat Jun 26 05:02:59 UTC 2021 , Edited by admin on Sat Jun 26 05:02:59 UTC 2021
PRIMARY
FDA UNII
8TR252Z538
Created by admin on Sat Jun 26 05:02:59 UTC 2021 , Edited by admin on Sat Jun 26 05:02:59 UTC 2021
PRIMARY
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