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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 of ETIOCHOLANOLONE

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
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

Curator's Comment:: Etiocholanolone have anticonvulsant properties in rodent models of epilepsy. No human data available.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis.
2001 Jan 22
Hemodynamic effects of a new inotropic compound, PST-2744, in dogs with chronic ischemic heart failure.
2003 Aug
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
Glucocorticoid metabolites inhibit the metabolism of androstenedione in red blood cells of ruminants.
2003 Mar
Studies on the radioprotective effect of etiocholanolone.
2004
Urinary steroid metabolites and 11beta-hydroxysteroid dehydrogenase activity in patients with unipolar recurrent major depression.
2004 Jul
Urinary analysis of four testosterone metabolites and pregnanediol by gas chromatography-combustion-isotope ratio mass spectrometry after oral administrations of testosterone.
2004 Sep
Isotopic fractionation of endogenous anabolic androgenic steroids and its relationship to doping control in sports.
2005 Jan
Anticonvulsant activity of androsterone and etiocholanolone.
2005 Jun
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
Enzyme kinetics of zearalenone biotransformation: pH and cofactor effects.
2005 Oct
Urine steroid profile of judo competitors affected by acute physical exercises.
2005 Sep
Liquorice in moderate doses does not affect sex steroid hormones of biological importance although the effect differs between the genders.
2006
Longitudinal profiling of urinary steroids by gas chromatography/combustion/isotope ratio mass spectrometry: diet change may result in carbon isotopic variations.
2006 Feb 2
Suppression of adrenal function by low-dose prednisone: assessment with 24-hour urinary steroid hormone profiles--a review of five cases.
2006 Mar
Detection of dehydroepiandrosterone misuse by means of gas chromatography- combustion-isotope ratio mass spectrometry.
2007
Istaroxime: a new luso-inotropic agent for heart failure.
2007 Jan 22
Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor.
2007 Jun
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
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.
2008 Jan
Isolation and quantification by high-performance liquid chromatography-ion-trap mass spectrometry of androgen sulfoconjugates in human urine.
2008 Jul 4
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
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
A randomized placebo-controlled study on the effects of pioglitazone on cortisol metabolism in polycystic ovary syndrome.
2009 Mar
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
Nandrolone excretion in sedentary vs physically trained young women.
2010 Feb
Patents

Sample Use Guides

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
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
Created by admin on Fri Jun 25 21:37:21 UTC 2021 , Edited by admin on Fri Jun 25 21:37:21 UTC 2021
NCI_THESAURUS C2139
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LOINC 34301-2
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LOINC 34303-8
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LOINC 15065-6
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LOINC 2266-5
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NCI_THESAURUS C2298
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LOINC 30508-6
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LOINC 82847-5
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LOINC 82851-7
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CFR 21 CFR 862.1285
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LOINC 56488-0
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LOINC 82846-7
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LOINC 13614-3
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LOINC 82881-4
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LOINC 82852-5
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LOINC 2268-1
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LOINC 44355-6
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LOINC 82882-2
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LOINC 2267-3
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LOINC 34302-0
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LOINC 80157-1
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LOINC 82853-3
Created by admin on Fri Jun 25 21:37:21 UTC 2021 , Edited by admin on Fri Jun 25 21:37:21 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C29023
Created by admin on Fri Jun 25 21:37:21 UTC 2021 , Edited by admin on Fri Jun 25 21:37:21 UTC 2021
PRIMARY
MESH
D005043
Created by admin on Fri Jun 25 21:37:21 UTC 2021 , Edited by admin on Fri Jun 25 21:37:21 UTC 2021
PRIMARY
WIKIPEDIA
ETIOCHOLANOLONE
Created by admin on Fri Jun 25 21:37:21 UTC 2021 , Edited by admin on Fri Jun 25 21:37:21 UTC 2021
PRIMARY
PUBCHEM
5880
Created by admin on Fri Jun 25 21:37:21 UTC 2021 , Edited by admin on Fri Jun 25 21:37:21 UTC 2021
PRIMARY
DRUG BANK
DB02854
Created by admin on Fri Jun 25 21:37:21 UTC 2021 , Edited by admin on Fri Jun 25 21:37:21 UTC 2021
PRIMARY
CAS
53-42-9
Created by admin on Fri Jun 25 21:37:21 UTC 2021 , Edited by admin on Fri Jun 25 21:37:21 UTC 2021
PRIMARY
FDA UNII
97CGB1M48I
Created by admin on Fri Jun 25 21:37:21 UTC 2021 , Edited by admin on Fri Jun 25 21:37:21 UTC 2021
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
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PARENT -> METABOLITE
MAJOR
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