ADRENOSTERONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H24O3
Molecular Weight	300.3921
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC(=O)[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C

InChI

InChIKey=RZRPTBIGEANTGU-IRIMSJTPSA-N

InChI=1S/C19H24O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H24O3
Molecular Weight	300.3921
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20355175 | http://prohormonedb.com/view-ingredients.asp?i=46&n=Androst-4-ene-3

Adrenosterone (androst-4-ene-3,11,17-trione, 11-oxoandrostenedione) is an endogenous steroid hormone that has been promoted as a dietary supplement capable of reducing body fat and increasing muscle mass. Adrenosterone has shown to be converted into 11-ketotestosterone in humans, which contributes to adrenosterone's androgenic effects. It is proposed that adrenosterone may function as an inhibitor of the 11beta-hydroxysteroid dehydrogenase type 1 enzyme (11beta-HSD1), which is primarily responsible for reactivation of cortisol from cortisone.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Solute carrier family 22 member 2 8 Target ID: CHEMBL1743122 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23034939	Inhibitor 8297
11-beta-hydroxysteroid dehydrogenase type 1 1 Target ID: CHEMBL5342 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16188377 \| https://www.ncbi.nlm.nih.gov/pubmed/20355175	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Androgen and behavior in the male three-spined stickleback, Gasterosteus aculeatus. II. Castration and 11-ketoandrostenedione effects on courtship and parental care during the nesting cycle.	2002 Nov	12460593
Stress adaptation, cortisol and pubertal development in the male common carp, Cyprinus carpio.	2002 Nov 29	12431803
Are the 11-oxo-steroids really so hindered towards organometallic compounds?	2004 Jan	14715373
Treatment of GnRHa-implanted Senegalese sole (Solea senegalensis) with 11-ketoandrostenedione stimulates spermatogenesis and increases sperm motility.	2007 Aug	17360211
Biotransformation of adrenosterone by filamentous fungus, Cunninghamella elegans.	2007 Dec	17889091
Synthetic organic chemistry based on small ring compounds.	2007 Jul	17603183
An experimental test of the immunocompetence handicap hypothesis in a teleost fish: 11-ketotestosterone suppresses innate immunity in three-spined sticklebacks.	2007 Oct	17891730
Functional characterization and expression analysis of the androgen receptor in zebrafish (Danio rerio) testis.	2008 Aug	18469035
Effects of castration and androgen-treatment on the expression of FSH-beta and LH-beta in the three-spine stickleback, gasterosteus aculeatus--feedback differences mediating the photoperiodic maturation response?	2008 Sep 1	18664367
2-D DIGE analysis of Senegalese sole (Solea senegalensis) testis proteome in wild-caught and hormone-treated F1 fish.	2009 Apr	19322785
Sex steroid-induced inhibition of food intake in sea bass (Dicentrarchus labrax).	2009 Jan	18709378
Development of criteria for the detection of adrenosterone administration by gas chromatography-mass spectrometry and gas chromatography-combustion-isotope ratio mass spectrometry for doping control.	2009 Nov	20355175
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

Common dosages as an anabolic supplement: 300mg to 900 mg daily.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:32:46 GMT 2023` Edited by `admin` on `Fri Dec 15 18:32:46 GMT 2023`
Record UNII	AE4E9102GY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ADRENOSTERONE

Common Name

English

NSC-12166

Code

English

ANDROST-4-ENE-3,11,17-TRIONE

Systematic Name

English

REICHSTEIN'S SUBSTANCE G

Common Name

English

ADRENOSTERONE [MI]

Common Name

English

Classification Tree Code System Code

WIKIPEDIA

Designer-drugs-Adrenosterone