EPIANDROSTERONE

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 Search

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

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22037250
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12054855	Antagonist 2778
Glucose-6-phosphate 1-dehydrogenase 12 Target ID: CHEMBL5347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7726568	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Inhibitors of pentose phosphate pathway cause vasodilation: involvement of voltage-gated potassium channels.	2002 Apr	11907187
Use of bioconversion for the preparation of [4-14C]-labeled 7 alpha- and 7 beta-hydroxylated derivatives of dehydroepiandrosterone and epiandrosterone.	2002 Dec	12441198
The effect of isoflavone extract ingestion, as Trinovin, on plasma steroids in normal men.	2002 Jan	11728518
Epiandrosterone, a metabolite of testosterone precursor, blocks L-type calcium channels of ventricular myocytes and inhibits myocardial contractility.	2002 Jun	12054855
A facile and high yielding synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide--an internal standard in dope.	2003 Jan	12575693
Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines.	2003 Jan	12475725
Hypoxia promotes relaxation of bovine coronary arteries through lowering cytosolic NADPH.	2006 Jun	16415080
Steroid hormone related male biased parasitism in chamois, Rupicapra rupicapra rupicapra.	2006 Jun 15	16497439
Effects of mutation at the D-JH junction on affinity, specificity, and idiotypy of anti-progesterone antibody DB3.	2006 Sep	16882990
Hexose-6-phosphate dehydrogenase modulates 11beta-hydroxysteroid dehydrogenase type 1-dependent metabolism of 7-keto- and 7beta-hydroxy-neurosteroids.	2007 Jun 27	17593962
Isolation and identification of diglucuronides of some endogenous steroids in dogs.	2008 Feb	18006648
Inhibition of Lassa virus glycoprotein cleavage and multicycle replication by site 1 protease-adapted alpha(1)-antitrypsin variants.	2009 Jun 2	19488405
Revealing genes associated with vitellogenesis in the liver of the zebrafish (Danio rerio) by transcriptome profiling.	2009 Mar 31	19335895
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	20570159
Determination of (13)C/(12)C ratios of endogenous urinary steroids excreted as sulpho conjugates.	2010 Nov 15	20941765
Steroid degradation genes in Comamonas testosteroni TA441: Isolation of genes encoding a Δ4(5)-isomerase and 3α- and 3β-dehydrogenases and evidence for a 100 kb steroid degradation gene hot spot.	2010 Oct	20554032

Patents

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

Name

Type

Language

EPIANDROSTERONE

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