U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ETIOCHOLANEDIONE

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

Description
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

Sources: Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1938), 71B, 156-8.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
20.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Molecular basis of crossreactivity and the limits of antibody-antigen complementarity.
1993 Oct 28
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
Closely related antibody receptors exploit fundamentally different strategies for steroid recognition.
2008 Aug 19
Patents

Patents

Sample Use Guides

4 g for 20-weeks
Route of Administration: Oral
In Vitro Use Guide
Unknown
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
Created by admin on Fri Dec 15 15:36:35 GMT 2023 , Edited by admin on Fri Dec 15 15:36:35 GMT 2023
FDA ORPHAN DRUG 92695
Created by admin on Fri Dec 15 15:36:35 GMT 2023 , Edited by admin on Fri Dec 15 15:36:35 GMT 2023
Code System Code Type Description
DRUG BANK
DB07375
Created by admin on Fri Dec 15 15:36:35 GMT 2023 , Edited by admin on Fri Dec 15 15:36:35 GMT 2023
PRIMARY
CHEBI
16985
Created by admin on Fri Dec 15 15:36:35 GMT 2023 , Edited by admin on Fri Dec 15 15:36:35 GMT 2023
PRIMARY
FDA UNII
213MVW2TZD
Created by admin on Fri Dec 15 15:36:35 GMT 2023 , Edited by admin on Fri Dec 15 15:36:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID10153778
Created by admin on Fri Dec 15 15:36:35 GMT 2023 , Edited by admin on Fri Dec 15 15:36:35 GMT 2023
PRIMARY
PUBCHEM
440114
Created by admin on Fri Dec 15 15:36:35 GMT 2023 , Edited by admin on Fri Dec 15 15:36:35 GMT 2023
PRIMARY
WIKIPEDIA
Etiocholanedione
Created by admin on Fri Dec 15 15:36:35 GMT 2023 , Edited by admin on Fri Dec 15 15:36:35 GMT 2023
PRIMARY
CAS
1229-12-5
Created by admin on Fri Dec 15 15:36:35 GMT 2023 , Edited by admin on Fri Dec 15 15:36:35 GMT 2023
PRIMARY