ETIOCHOLANOLONE

Investigational

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 Search

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
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 27 Target ID: CHEMBL2095167 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17341652 \| https://www.ncbi.nlm.nih.gov/pubmed/17434649	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15946323	Primary		Basic research	Unknown Approved Use Unknown
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12441187	Primary		Basic research	Unknown Approved Use Unknown

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	11746924
Metabolism of orally administered androstenedione in young men.	2001 Aug	11502792
Changes in androgenic steroid profile due to urine contamination by microorganisms: a prospective study in the context of doping control.	2001 Feb 15	11161304
Putative steroidal pheromones in the round goby, Neogobius melanostomus: olfactory and behavioral responses.	2001 Mar	11441438
Pharmacological profile of the novel inotropic agent (E,Z)-3-((2-aminoethoxy)imino)androstane-6,17-dione hydrochloride (PST2744).	2002 Nov	12388640
Hemodynamic effects of a new inotropic compound, PST-2744, in dogs with chronic ischemic heart failure.	2003 Aug	12883318
Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines.	2003 Jan	12475725
Urinary excretion of steroid metabolites after chronic androstenedione ingestion.	2004 Dec	15579782
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	15576469
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
Enzyme kinetics of zearalenone biotransformation: pH and cofactor effects.	2005 Oct	15937666
Hypothalamic-pituitary-adrenal axis modulation of GABAergic neuroactive steroids influences ethanol sensitivity and drinking behavior.	2006	17290803
Steroids and thermogenesis.	2006	15910167
Variations in urine excretion of steroid hormones after an acute session and after a 4-week programme of strength training.	2007 Jan	17051372
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	17239705
Istaroxime: a new luso-inotropic agent for heart failure.	2007 Jan 22	17239702
Evolution of pharmacologic specificity in the pregnane X receptor.	2008 Apr 2	18384689
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.	2008 Jan	17434649
[Determination of endogenous anabolic steroids in hair using gas chromatography-tandem mass spectrometry].	2008 Jul	18959241
Determination of 13C/12C ratios of endogenous urinary steroids: method validation, reference population and application to doping control purposes.	2008 Jul	18536069
Istaroxime in heart failure new hope or more hype.	2008 Jun 10	18534277
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	18496261
The urinary steroid profile in patients diagnosed with adrenal incidentaloma.	2009 Apr	19297679
Dietary enterolactone affects androgen and estrogen levels in healthy postmenopausal women.	2009 Feb	19250209
Determination of the deuterium/hydrogen ratio of endogenous urinary steroids for doping control purposes.	2009 Jul	19462405
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
Isotope ratio mass spectrometry analysis of the oxidation products of the main and minor metabolites of hydrocortisone and cortisone for antidoping controls.	2009 Mar	19056411
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

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 Dec 15 16:18:33 UTC 2023` Edited by `admin` on `Fri Dec 15 16:18:33 UTC 2023`
Record UNII	97CGB1M48I
Record Status	`Validated (UNII)`
Record Version

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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