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
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15946323Curator'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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15946323
Curator's Comment:: Etiocholanolone have anticonvulsant properties in rodent models of epilepsy. No human data available.
Approval Year
PubMed
Title | Date | PubMed |
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Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis. | 2001 Jan 22 |
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Hemodynamic effects of a new inotropic compound, PST-2744, in dogs with chronic ischemic heart failure. | 2003 Aug |
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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 |
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Glucocorticoid metabolites inhibit the metabolism of androstenedione in red blood cells of ruminants. | 2003 Mar |
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Studies on the radioprotective effect of etiocholanolone. | 2004 |
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Urinary steroid metabolites and 11beta-hydroxysteroid dehydrogenase activity in patients with unipolar recurrent major depression. | 2004 Jul |
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Urinary analysis of four testosterone metabolites and pregnanediol by gas chromatography-combustion-isotope ratio mass spectrometry after oral administrations of testosterone. | 2004 Sep |
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Isotopic fractionation of endogenous anabolic androgenic steroids and its relationship to doping control in sports. | 2005 Jan |
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Anticonvulsant activity of androsterone and etiocholanolone. | 2005 Jun |
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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 |
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Enzyme kinetics of zearalenone biotransformation: pH and cofactor effects. | 2005 Oct |
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Urine steroid profile of judo competitors affected by acute physical exercises. | 2005 Sep |
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Liquorice in moderate doses does not affect sex steroid hormones of biological importance although the effect differs between the genders. | 2006 |
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Longitudinal profiling of urinary steroids by gas chromatography/combustion/isotope ratio mass spectrometry: diet change may result in carbon isotopic variations. | 2006 Feb 2 |
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Suppression of adrenal function by low-dose prednisone: assessment with 24-hour urinary steroid hormone profiles--a review of five cases. | 2006 Mar |
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Detection of dehydroepiandrosterone misuse by means of gas chromatography- combustion-isotope ratio mass spectrometry. | 2007 |
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Istaroxime: a new luso-inotropic agent for heart failure. | 2007 Jan 22 |
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Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor. | 2007 Jun |
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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 |
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Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens. | 2008 Jan |
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Isolation and quantification by high-performance liquid chromatography-ion-trap mass spectrometry of androgen sulfoconjugates in human urine. | 2008 Jul 4 |
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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 |
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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 |
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A randomized placebo-controlled study on the effects of pioglitazone on cortisol metabolism in polycystic ovary syndrome. | 2009 Mar |
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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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12475725
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
Edited
Fri Jun 25 21:37:21 UTC 2021
by
admin
on
Fri Jun 25 21:37:21 UTC 2021
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Record UNII |
97CGB1M48I
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Record Status |
Validated (UNII)
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Record Version |
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LOINC |
82850-9
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NCI_THESAURUS |
C2139
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LOINC |
34301-2
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34303-8
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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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82847-5
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82851-7
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CFR |
21 CFR 862.1285
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56488-0
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82846-7
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13614-3
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82881-4
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82852-5
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2268-1
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44355-6
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LOINC |
82882-2
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2267-3
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34302-0
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80157-1
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82853-3
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Code System | Code | Type | Description | ||
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C29023
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D005043
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ETIOCHOLANOLONE
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5880
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DB02854
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53-42-9
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97CGB1M48I
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admin on Fri Jun 25 21:37:21 UTC 2021 , Edited by admin on Fri Jun 25 21:37:21 UTC 2021
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Related Record | Type | Details | ||
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METABOLITE -> PARENT | |||
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PARENT -> METABOLITE TOXIC |
Metabolite shown to induce pyrogenic and inflammatory reactions in man.
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PARENT -> METABOLITE |
MAJOR
URINE
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