ETIOCHOLANOLONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H30O2
Molecular Weight	290.441
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]12CC[C@]([H])(C[C@@]2([H])CC[C@@]3([H])[C@]4([H])CCC(=O)[C@@]4(C)CC[C@@]31[H])O

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

Molecular Formula	C19H30O2
Molecular Weight	290.441
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/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 21 Target ID: CHEMBL2095167 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17341652 \| https://www.ncbi.nlm.nih.gov/pubmed/17434649	Positive Allosteric Modulator 155

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 116 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15946323	Primary		Basic research	Unknown Approved Use Unknown
Hypertension 513 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12441187	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis.	2001 Jan 22	11165029
Hemodynamic effects of a new inotropic compound, PST-2744, in dogs with chronic ischemic heart failure.	2003 Aug	12883318
Structure-based design and synthesis of novel potent Na+,K+ -ATPase inhibitors derived from a 5alpha,14alpha-androstane scaffold as positive inotropic compounds.	2003 Aug 14	12904068
Glucocorticoid metabolites inhibit the metabolism of androstenedione in red blood cells of ruminants.	2003 Mar	12667200
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
Urinary analysis of four testosterone metabolites and pregnanediol by gas chromatography-combustion-isotope ratio mass spectrometry after oral administrations of testosterone.	2004 Sep	15516291
Isotopic fractionation of endogenous anabolic androgenic steroids and its relationship to doping control in sports.	2005 Jan	15808004
Anticonvulsant activity of androsterone and etiocholanolone.	2005 Jun	15946323
Investigation of the feeding effect on the 13C/12C isotope ratio of the hormones in bovine urine using gas chromatography/combustion isotope ratio mass spectrometry.	2005 Mar 4	15844538
Enzyme kinetics of zearalenone biotransformation: pH and cofactor effects.	2005 Oct	15937666
Urine steroid profile of judo competitors affected by acute physical exercises.	2005 Sep	16212787
Liquorice in moderate doses does not affect sex steroid hormones of biological importance although the effect differs between the genders.	2006	16462145
Longitudinal profiling of urinary steroids by gas chromatography/combustion/isotope ratio mass spectrometry: diet change may result in carbon isotopic variations.	2006 Feb 2	16338181
Suppression of adrenal function by low-dose prednisone: assessment with 24-hour urinary steroid hormone profiles--a review of five cases.	2006 Mar	16597193
Detection of dehydroepiandrosterone misuse by means of gas chromatography- combustion-isotope ratio mass spectrometry.	2007	18417762
Istaroxime: a new luso-inotropic agent for heart failure.	2007 Jan 22	17239702
Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor.	2007 Jun	17341652
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
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.	2008 Jan	17434649
Isolation and quantification by high-performance liquid chromatography-ion-trap mass spectrometry of androgen sulfoconjugates in human urine.	2008 Jul 4	18501914
Hemodynamic, echocardiographic, and neurohormonal effects of istaroxime, a novel intravenous inotropic and lusitropic agent: a randomized controlled trial in patients hospitalized with heart failure.	2008 Jun 10	18534276
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
A randomized placebo-controlled study on the effects of pioglitazone on cortisol metabolism in polycystic ovary syndrome.	2009 Mar	18402944
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
Nandrolone excretion in sedentary vs physically trained young women.	2010 Feb	19170961

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.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:37:21 UTC 2021` Edited by `admin` on `Fri Jun 25 21:37:21 UTC 2021`
Record UNII	97CGB1M48I
Record Status	`Validated (UNII)`
Record Version

Download

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