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

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
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 28 Target ID: CHEMBL2095167 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17341652 \| https://www.ncbi.nlm.nih.gov/pubmed/17434649	Positive Allosteric Modulator 186

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 575 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12441187	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
UGT2B23, a novel uridine diphosphate-glucuronosyltransferase enzyme expressed in steroid target tissues that conjugates androgen and estrogen metabolites.	1999 Dec	10579317
Metabolism of orally administered androstenedione in young men.	2001 Aug	11502792
[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
Urinary steroids in men with male-pattern alopecia.	2002 Oct-Nov	12406594
Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines.	2003 Jan	12475725
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
Urinary markers of adrenarche: reference values in healthy subjects, aged 3-18 years.	2005 Apr	15671100
5alpha-reductase in human embryonic kidney cell line HEK293: evidence for type II enzyme expression and activity.	2005 Feb	15792368
Anticonvulsant activity of androsterone and etiocholanolone.	2005 Jun	15946323
Enzyme kinetics of zearalenone biotransformation: pH and cofactor effects.	2005 Oct	15937666
Dehydroepiandrosterone and its derivatives: potentially novel anti-proliferative and chemopreventive agents.	2006	17017935
Urine steroid hormone profile analysis in cytochrome P450 oxidoreductase deficiency: implication for the backdoor pathway to dihydrotestosterone.	2006 Jul	16608896
Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor.	2007 Jun	17341652
Mechanism of proton transfer in the 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni.	2007 Nov 23	17893142
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.	2008 Jan	17434649
The urinary steroid profile in patients diagnosed with adrenal incidentaloma.	2009 Apr	19297679
Determination of the deuterium/hydrogen ratio of endogenous urinary steroids for doping control purposes.	2009 Jul	19462405
Analysis of conjugated steroid androgens: deconjugation, derivatisation and associated issues.	2009 Jul 12	19304432
Nandrolone excretion in sedentary vs physically trained young women.	2010 Feb	19170961

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 `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

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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