ETIOCHOLANOLONE

Investigational

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-BNSUEQOYSA-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+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15946323
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/5480865 | https://www.ncbi.nlm.nih.gov/pubmed/16695933 | https://www.ncbi.nlm.nih.gov/pubmed/17341652

Etiocholanone is an androstane neurosteroid. Etiocholanone potentiates GABA-A receptor currents and exerts anticolvunsant properties in rodents. Etiocholanolone demostrates pyrogenic properties.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; alpha-1/beta-2/gamma-2 27 Target ID: CHEMBL2095167 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17341652 \| https://www.ncbi.nlm.nih.gov/pubmed/17434649	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15946323	Primary		Basic research	Unknown Approved Use Unknown
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12441187	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Gas chromatography/combustion/isotope ratio mass spectrometry to control the misuse of androgens in breeding animals: new derivatisation method applied to testosterone metabolites and precursors in urine samples.	2001	11746924
Diethylstilbestrol regulates trophoblast stem cell differentiation as a ligand of orphan nuclear receptor ERR beta.	2001 Apr 1	11297507
Changes in androgenic steroid profile due to urine contamination by microorganisms: a prospective study in the context of doping control.	2001 Feb 15	11161304
Putative steroidal pheromones in the round goby, Neogobius melanostomus: olfactory and behavioral responses.	2001 Mar	11441438
Pharmacological profile of the novel inotropic agent (E,Z)-3-((2-aminoethoxy)imino)androstane-6,17-dione hydrochloride (PST2744).	2002 Nov	12388640
Urinary steroids in men with male-pattern alopecia.	2002 Oct-Nov	12406594
Diverse toxicity associated with cardiac Na+/K+ pump inhibition: evaluation of electrophysiological mechanisms.	2003 May	12606646
Studies on the radioprotective effect of etiocholanolone.	2004	18084866
Urinary steroid metabolites and 11beta-hydroxysteroid dehydrogenase activity in patients with unipolar recurrent major depression.	2004 Jul	15183600
Production rates of cortisol in obesity.	2004 Sep	15483206
Urinary steroid excretion rates in acromegaly.	2005	15900108
Modulation of sarcoplasmic reticulum function by Na+/K+ pump inhibitors with different toxicity: digoxin and PST2744 [(E,Z)-3-((2-aminoethoxy)imino)androstane-6,17-dione hydrochloride].	2005 Apr	15576469
Isotopic fractionation of endogenous anabolic androgenic steroids and its relationship to doping control in sports.	2005 Jan	15808004
In vitro biosynthesis of novel 5beta-reduced steroids by the testis of the round goby, Neogobius melanostomus.	2005 Jan 1	15596066
Steroids and thermogenesis.	2006	15910167
Application of stable carbon isotope analysis to the detection of testosterone administration to cattle.	2006 Apr 19	16608200
Emerging therapies for the management of decompensated heart failure: from bench to bedside.	2006 Dec 19	17174176
Determination of the origin of urinary norandrosterone traces by gas chromatography combustion isotope ratio mass spectrometry.	2006 Sep	17047802
Targeting SERCA2a as an innovative approach to the therapy of congestive heart failure.	2007	17113239
Variations in urine excretion of steroid hormones after an acute session and after a 4-week programme of strength training.	2007 Jan	17051372
A phase 1-2 dose-escalating study evaluating the safety and tolerability of istaroxime and specific effects on electrocardiographic and hemodynamic parameters in patients with chronic heart failure with reduced systolic function.	2007 Jan 22	17239705
Istaroxime: an investigational luso-inotropic agent for acute heart failure syndromes.	2007 Jan 22	17239700
The neuro-steroid, 3beta androstene 17alpha diol exhibits potent cytotoxic effects on human malignant glioma and lymphoma cells through different programmed cell death pathways.	2007 Sep 3	17637679
Overview of emerging pharmacologic agents for acute heart failure syndromes.	2008 Feb	18279775
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.	2008 Jan	17434649
Short term impact of Tribulus terrestris intake on doping control analysis of endogenous steroids.	2008 Jun 10	18282674
Direct quantification of steroid glucuronides in human urine by liquid chromatography-electrospray tandem mass spectrometry.	2008 Mar 7	18258241
The effects of sex, age and commensal way of life on levels of fecal glucocorticoid metabolites in spiny mice (Acomys cahirinus).	2008 Sep 3	18586285
The urinary steroid profile in patients diagnosed with adrenal incidentaloma.	2009 Apr	19297679
Detection of testosterone administration based on the carbon isotope ratio profiling of endogenous steroids: international reference populations of professional soccer players.	2009 Dec	19549614
Istaroxime, a first in class new chemical entity exhibiting SERCA-2 activation and Na-K-ATPase inhibition: a new promising treatment for acute heart failure syndromes?	2009 Dec	19238540
Dietary enterolactone affects androgen and estrogen levels in healthy postmenopausal women.	2009 Feb	19250209
Physiological concentrations of anabolic steroids in human hair.	2009 Jan 30	19131197
Determination of the deuterium/hydrogen ratio of endogenous urinary steroids for doping control purposes.	2009 Jul	19462405
Drug testing data from the 2007 Pan American Games: delta13C values of urinary androsterone, etiocholanolone and androstanediols determined by GC/C/IRMS.	2009 Jul	19428237
Effects of istaroxime on diastolic stiffness in acute heart failure syndromes: results from the Hemodynamic, Echocardiographic, and Neurohormonal Effects of Istaroxime, a Novel Intravenous Inotropic and Lusitropic Agent: a Randomized Controlled Trial in Patients Hospitalized with Heart Failure (HORIZON-HF) trial.	2009 Jun	19464414
Isotope ratio mass spectrometry analysis of the oxidation products of the main and minor metabolites of hydrocortisone and cortisone for antidoping controls.	2009 Mar	19056411
Urinary and serum hormones profiles after testosterone enanthate administration in male hypogonadism: concerns on the detection of doping with testosterone in treated hypogonadal athletes.	2009 May	19461217
The effects of DHEA, 3beta-hydroxy-5alpha-androstane-6,17-dione, and 7-amino-DHEA analogues on short term and long term memory in the mouse.	2009 Nov	19577585

Patents

Sample Use Guides

In Vivo Use Guide

After increasing diastolic blood pressure (DBP) in rats by a continuous infusion of norepinephrine (0.059 uM/kg/min), intravenous bolus injections of etiocholanolone (5-25 uM/kg) produced dose-dependent vasodepressor responses. Etiocholanolone (intraperitoneal injection) have anticonvulsant properties in rodent models of epilepsy: it was active in the 6-Hz and pentylenetetrazol models (ED50 values, 76.9 and 139 mg/kg, respectively),

Route of Administration: Other

In Vitro Use Guide

10-100 uM etiocholanolone in a dose- and time-dependent manner has an anti-proliferative action on human cancer cell lines.

Name

Type

Language

ETIOCHOLANOLONE

Common Name

English

J4.146G

Code

English

3.ALPHA.-HYDROXY-5.BETA.-ANDROSTAN-17-ONE

Systematic Name

English

5.BETA.-ANDROSTERONE

Common Name

English

5.BETA.-ANDROSTAN-17-ONE, 3.ALPHA.-HYDROXY-

Systematic Name

English

AETIOCHOLANOLONE

Common Name

English

.ALPHA.-ETIOCHOLANOLONE

Common Name

English

ETIOCHOLAN-3.ALPHA.-OL-17-ONE

Common Name

English

NSC-50908

Code

English

5-ISOANDROSTERONE

Common Name

English

Classification Tree Code System Code

LOINC

82850-9