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

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
Testosterone-induced relaxation of rat aorta is androgen structure specific and involves K+ channel activation.	2001 Dec	11717242
Putative steroidal pheromones in the round goby, Neogobius melanostomus: olfactory and behavioral responses.	2001 Mar	11441438
The role of the liver in the acute effect of alcohol on androgens in women.	2001 May	11344195
Energetic analysis of binding of progesterone and 5 beta-androstane-3,17-dione to anti-progesterone antibody DB3 using molecular dynamics and free energy calculations.	2001 Oct	11739893
[Urinary nandrolone metabolites in antidoping control].	2001 Sep	11787429
Detection of epitestosterone doping by isotope ratio mass spectrometry.	2002	11901061
Artifact formation due to ethyl thio-incorporation into silylated steroid structures as determined in doping analysis.	2002 Apr 19	12058904
Pharmacological profile of the novel inotropic agent (E,Z)-3-((2-aminoethoxy)imino)androstane-6,17-dione hydrochloride (PST2744).	2002 Nov	12388640
Urinary steroids in men with male-pattern alopecia.	2002 Oct-Nov	12406594
Methyl-testosterone induces male-typical ventilatory behavior in response to putative steroidal pheromones in female round gobies (Neogobius melanostomus).	2002 Sep	12367564
Hemodynamic effects of a new inotropic compound, PST-2744, in dogs with chronic ischemic heart failure.	2003 Aug	12883318
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	12904068
Altered cortisol metabolism in polycystic ovary syndrome: insulin enhances 5alpha-reduction but not the elevated adrenal steroid production rates.	2003 Dec	14671189
Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines.	2003 Jan	12475725
Effects of androgens on aromatase activity and 11C-vorozole binding in granulosa cells in vitro.	2003 Mar	12694114
Glucocorticoid metabolites inhibit the metabolism of androstenedione in red blood cells of ruminants.	2003 Mar	12667200
Diverse toxicity associated with cardiac Na+/K+ pump inhibition: evaluation of electrophysiological mechanisms.	2003 May	12606646
Studies on the radioprotective effect of etiocholanolone.	2004	18084866
Endogenous urinary steroids in premenopausal women with uterine leiomyomas.	2004 Jan	14698830
Urinary steroid metabolites and 11beta-hydroxysteroid dehydrogenase activity in patients with unipolar recurrent major depression.	2004 Jul	15183600
Urinary steroid excretion rates in acromegaly.	2005	15900108
Urinary markers of adrenarche: reference values in healthy subjects, aged 3-18 years.	2005 Apr	15671100
Isotopic fractionation of endogenous anabolic androgenic steroids and its relationship to doping control in sports.	2005 Jan	15808004
Formation of 19-norsteroids by in situ demethylation of endogenous steroids in stored urine samples.	2005 Jul	15894033
Anticonvulsant activity of androsterone and etiocholanolone.	2005 Jun	15946323
Enzyme kinetics of zearalenone biotransformation: pH and cofactor effects.	2005 Oct	15937666
Urine steroid profile of judo competitors affected by acute physical exercises.	2005 Sep	16212787
Hypothalamic-pituitary-adrenal axis modulation of GABAergic neuroactive steroids influences ethanol sensitivity and drinking behavior.	2006	17290803
Liquorice in moderate doses does not affect sex steroid hormones of biological importance although the effect differs between the genders.	2006	16462145
Steroids and thermogenesis.	2006	15910167
Urine steroid hormone profile analysis in cytochrome P450 oxidoreductase deficiency: implication for the backdoor pathway to dihydrotestosterone.	2006 Jul	16608896
Detection of dehydroepiandrosterone misuse by means of gas chromatography- combustion-isotope ratio mass spectrometry.	2007	18417762
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
Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor.	2007 Jun	17341652
[New therapeutic goals--new drugs in heart failure treatment].	2007 Nov	18058588
Mechanism of proton transfer in the 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni.	2007 Nov 23	17893142
Istaroxime, a novel luso-inotropic agent for the treatment of acute heart failure.	2007 Sep	17729189
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	17637679
delta13C-values of endogenous urinary steroids.	2008 Apr	18241901
Evolution of pharmacologic specificity in the pregnane X receptor.	2008 Apr 2	18384689
Novel analogues of istaroxime, a potent inhibitor of Na+,K+-ATPase: synthesis and structure-activity relationship.	2008 Aug 14	18637667
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.	2008 Jan	17434649
Factors influencing the steroid profile in doping control analysis.	2008 Jul	18570179
Determination of urine steroid profile in untrained men to evaluate recovery after a strength training session.	2008 Jul	18545203
Determination of 13C/12C ratios of endogenous urinary steroids: method validation, reference population and application to doping control purposes.	2008 Jul	18536069
Modulation of sarcoplasmic reticulum function by PST2744 [istaroxime; (E,Z)-3-((2-aminoethoxy)imino) androstane-6,17-dione hydrochloride)] in a pressure-overload heart failure model.	2008 Sep	18539651
Physiological concentrations of anabolic steroids in human hair.	2009 Jan 30	19131197
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	19577585

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.

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