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

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

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
UGT2B23, a novel uridine diphosphate-glucuronosyltransferase enzyme expressed in steroid target tissues that conjugates androgen and estrogen metabolites.
1999 Dec
Metabolism of orally administered androstenedione in young men.
2001 Aug
[Urinary nandrolone metabolites in antidoping control].
2001 Sep
Detection of epitestosterone doping by isotope ratio mass spectrometry.
2002
Artifact formation due to ethyl thio-incorporation into silylated steroid structures as determined in doping analysis.
2002 Apr 19
Urinary steroids in men with male-pattern alopecia.
2002 Oct-Nov
Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines.
2003 Jan
Glucocorticoid metabolites inhibit the metabolism of androstenedione in red blood cells of ruminants.
2003 Mar
Diverse toxicity associated with cardiac Na+/K+ pump inhibition: evaluation of electrophysiological mechanisms.
2003 May
Urinary markers of adrenarche: reference values in healthy subjects, aged 3-18 years.
2005 Apr
5alpha-reductase in human embryonic kidney cell line HEK293: evidence for type II enzyme expression and activity.
2005 Feb
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
Urine steroid hormone profile analysis in cytochrome P450 oxidoreductase deficiency: implication for the backdoor pathway to dihydrotestosterone.
2006 Jul
Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor.
2007 Jun
Mechanism of proton transfer in the 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni.
2007 Nov 23
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.
2008 Jan
The urinary steroid profile in patients diagnosed with adrenal incidentaloma.
2009 Apr
Determination of the deuterium/hydrogen ratio of endogenous urinary steroids for doping control purposes.
2009 Jul
Analysis of conjugated steroid androgens: deconjugation, derivatisation and associated issues.
2009 Jul 12
Nandrolone excretion in sedentary vs physically trained young women.
2010 Feb
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 Mon Mar 31 18:24:41 GMT 2025
Edited
by admin
on Mon Mar 31 18:24:41 GMT 2025
Record UNII
97CGB1M48I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
J4.146G
Preferred Name English
ETIOCHOLANOLONE
Common Name 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 Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
NCI_THESAURUS C2139
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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
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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 Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID001018919
Created by admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
PRIMARY
NCI_THESAURUS
C29023
Created by admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
PRIMARY
CHEBI
28195
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PRIMARY
MESH
D005043
Created by admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
PRIMARY
WIKIPEDIA
ETIOCHOLANOLONE
Created by admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
PRIMARY
PUBCHEM
5880
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PRIMARY
DRUG BANK
DB02854
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PRIMARY
CAS
53-42-9
Created by admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
PRIMARY
FDA UNII
97CGB1M48I
Created by admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
PARENT -> METABOLITE TOXIC
PARENT -> METABOLITE
MAJOR
URINE