ETIOCHOLANEDIONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H28O2
Molecular Weight	288.4244
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
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])CC(=O)CC[C@]34C

InChI

InChIKey=RAJWOBJTTGJROA-QJISAEMRSA-N

InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14+,15+,16+,18+,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H28O2
Molecular Weight	288.4244
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16353603
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/3783591 | https://www.ncbi.nlm.nih.gov/pubmed/12161001 | https://www.ncbi.nlm.nih.gov/pubmed/13795320

Etiocholanedione is a natural metabolite of dehydroepiandrosterone with potent antiobesity activity. Etiocholanedione has been identified as a metabolite of an altered androgen metabolism that eventually leads hepatocellular carcinoma to impaired hormone responsiveness in human. Etiocholanedione has been identified as a metabolite of 17alpha-hydroxyprogesterone in some patients affected by congenital adrenal hyperplasia, although it doesn't appear to account for the masculinization observed in congenital hyperplasia.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3783591	Antagonist 2778		20.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16353603	Primary		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Molecular basis of crossreactivity and the limits of antibody-antigen complementarity.	1993 Oct 28	8413674
Increased 21-hydroxylase and shutdown of C(17,20) lyase activities in testicular tissues of the grouper (Epinephelus coioides) during 17alpha-methyltestosterone-induced sex inversion.	2002 May	12093117
Closely related antibody receptors exploit fundamentally different strategies for steroid recognition.	2008 Aug 19	18689687

Patents

Sample Use Guides

In Vivo Use Guide

4 g for 20-weeks

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:36:35 GMT 2023` Edited by `admin` on `Fri Dec 15 15:36:35 GMT 2023`
Record UNII	213MVW2TZD
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ETIOCHOLANEDIONE

Common Name

English

5.BETA.-ANDROSTANEDIONE

Systematic Name

English

ETIOCHOLANE-3,17-DIONE

Common Name

English

5.BETA.-ANDROSTANE-3,17-DIONE

Systematic Name

English

ANDROSTANE-3,17-DIONE, (5.BETA.)-

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

95896