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

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 of ETIOCHOLANOLONE

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

Molecular Formula C19H30O2
Molecular Weight 290.4403
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
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
Testosterone-induced relaxation of rat aorta is androgen structure specific and involves K+ channel activation.
2001 Dec
[Urinary nandrolone metabolites in antidoping control].
2001 Sep
Artifact formation due to ethyl thio-incorporation into silylated steroid structures as determined in doping analysis.
2002 Apr 19
Pharmacological profile of the novel inotropic agent (E,Z)-3-((2-aminoethoxy)imino)androstane-6,17-dione hydrochloride (PST2744).
2002 Nov
Methyl-testosterone induces male-typical ventilatory behavior in response to putative steroidal pheromones in female round gobies (Neogobius melanostomus).
2002 Sep
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
Urinary excretion of steroid metabolites after chronic androstenedione ingestion.
2004 Dec
Endogenous urinary steroids in premenopausal women with uterine leiomyomas.
2004 Jan
Reaction of (13S)-13-iodo-6beta-methoxy-3alpha,5-cyclo-13,14-seco-5alpha-androstane-14,17-dione with hydroxylamine and its application to the synthesis of new 13,14-seco steroids.
2004 Jul
Urinary analysis of 16(5alpha)-androsten-3alpha-ol by gas chromatography/combustion/isotope ratio mass spectrometry: implications in anti-doping analysis.
2004 Oct 15
Urinary steroid excretion rates in acromegaly.
2005
5alpha-reductase in human embryonic kidney cell line HEK293: evidence for type II enzyme expression and activity.
2005 Feb
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
Enzyme kinetics of zearalenone biotransformation: pH and cofactor effects.
2005 Oct
Dehydroepiandrosterone and its derivatives: potentially novel anti-proliferative and chemopreventive agents.
2006
Application of stable carbon isotope analysis to the detection of testosterone administration to cattle.
2006 Apr 19
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
Determination of the origin of urinary norandrosterone traces by gas chromatography combustion isotope ratio mass spectrometry.
2006 Sep
Detection of dehydroepiandrosterone misuse by means of gas chromatography- combustion-isotope ratio mass spectrometry.
2007
Targeting SERCA2a as an innovative approach to the therapy of congestive heart failure.
2007
Solvent effects on infrared spectra of progesterone in CHCl3/cyclo-C6H12 binary solvent systems.
2007 Jan
Variations in urine excretion of steroid hormones after an acute session and after a 4-week programme of strength training.
2007 Jan
Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor.
2007 Jun
Evolution of pharmacologic specificity in the pregnane X receptor.
2008 Apr 2
Determination of urine steroid profile in untrained men to evaluate recovery after a strength training session.
2008 Jul
Isolation and quantification by high-performance liquid chromatography-ion-trap mass spectrometry of androgen sulfoconjugates in human urine.
2008 Jul 4
Rationale and design of 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.
2008 May-Jun
The effects of sex, age and commensal way of life on levels of fecal glucocorticoid metabolites in spiny mice (Acomys cahirinus).
2008 Sep 3
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
Dietary enterolactone affects androgen and estrogen levels in healthy postmenopausal women.
2009 Feb
Drug testing data from the 2007 Pan American Games: delta13C values of urinary androsterone, etiocholanolone and androstanediols determined by GC/C/IRMS.
2009 Jul
Analysis of conjugated steroid androgens: deconjugation, derivatisation and associated issues.
2009 Jul 12
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
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
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 Dec 15 16:18:33 GMT 2023
Edited
by admin
on Fri Dec 15 16:18:33 GMT 2023
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 Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
NCI_THESAURUS C2139
Created by admin on Fri Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
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
Created by admin on Fri Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
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
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Code System Code Type Description
NSC
50908
Created by admin on Fri Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID001018919
Created by admin on Fri Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
PRIMARY
NCI_THESAURUS
C29023
Created by admin on Fri Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
PRIMARY
CHEBI
28195
Created by admin on Fri Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
PRIMARY
MESH
D005043
Created by admin on Fri Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
PRIMARY
WIKIPEDIA
ETIOCHOLANOLONE
Created by admin on Fri Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
PRIMARY
PUBCHEM
5880
Created by admin on Fri Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
PRIMARY
DRUG BANK
DB02854
Created by admin on Fri Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
PRIMARY
CAS
53-42-9
Created by admin on Fri Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
PRIMARY
FDA UNII
97CGB1M48I
Created by admin on Fri Dec 15 16:18:34 GMT 2023 , Edited by admin on Fri Dec 15 16:18:34 GMT 2023
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
PARENT -> METABOLITE
MAJOR
URINE
PARENT -> METABOLITE TOXIC
Metabolite shown to induce pyrogenic and inflammatory reactions in man.