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

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
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
Steroid hormone related male biased parasitism in chamois, Rupicapra rupicapra rupicapra.	2006 Jun 15	16497439
Trace analysis of androgens and progestogens in environmental waters by ultra-performance liquid chromatography-electrospray tandem mass spectrometry.	2008 Jun 27	18502434
Epimerase activity of the human 11beta-hydroxysteroid dehydrogenase type 1 on 7-hydroxylated C19-steroids.	2009 Mar	19167490
Revealing genes associated with vitellogenesis in the liver of the zebrafish (Danio rerio) by transcriptome profiling.	2009 Mar 31	19335895
Effects of valproate and carbamazepine monotherapy on neuroactive steroids, their precursors and metabolites in adult men with epilepsy.	2010 Oct	20541012

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:19:53 GMT 2023` Edited by `admin` on `Fri Dec 15 15:19:53 GMT 2023`
Record UNII	8TR252Z538
Record Status	`Validated (UNII)`
Record Version

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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