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
SMILES
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](O)CC[C@]34C)[C@@H]1CCC2=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
DescriptionCurator'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
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.
Approval Year
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 |
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| Changes in androgenic steroid profile due to urine contamination by microorganisms: a prospective study in the context of doping control. | 2001 Feb 15 |
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| The role of the liver in the acute effect of alcohol on androgens in women. | 2001 May |
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| Urinary excretion of steroid metabolites after chronic androstenedione ingestion. | 2004 Dec |
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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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| Production rates of cortisol in obesity. | 2004 Sep |
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| Urinary markers of adrenarche: reference values in healthy subjects, aged 3-18 years. | 2005 Apr |
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| 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 |
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| 5alpha-reductase in human embryonic kidney cell line HEK293: evidence for type II enzyme expression and activity. | 2005 Feb |
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| Isotopic fractionation of endogenous anabolic androgenic steroids and its relationship to doping control in sports. | 2005 Jan |
|
| In vitro biosynthesis of novel 5beta-reduced steroids by the testis of the round goby, Neogobius melanostomus. | 2005 Jan 1 |
|
| Formation of 19-norsteroids by in situ demethylation of endogenous steroids in stored urine samples. | 2005 Jul |
|
| Urinary marker of oral pregnenolone administration. | 2005 Mar |
|
| 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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| Hypothalamic-pituitary-adrenal axis modulation of GABAergic neuroactive steroids influences ethanol sensitivity and drinking behavior. | 2006 |
|
| 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 |
|
| Hemodynamic properties of a new-generation positive luso-inotropic agent for the acute treatment of advanced 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 |
|
| Istaroxime, a novel luso-inotropic agent for the treatment of acute heart failure. | 2007 Sep |
|
| 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 |
|
| Short term impact of Tribulus terrestris intake on doping control analysis of endogenous steroids. | 2008 Jun 10 |
|
| Sympathomimetic inefficiency in restoring contractility in the acute or chronic beta-blocker-treated ischaemic heart: comparison with a new agent. | 2008 Oct |
|
| 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 |
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:
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D005043
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ETIOCHOLANOLONE
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97CGB1M48I
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METABOLITE (PARENT)
PARENT (METABOLITE TOXIC)
PARENT (METABOLITE)
SUBSTANCE RECORD
