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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15946323Curator'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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15946323
Curator's Comment: Etiocholanolone have anticonvulsant properties in rodent models of epilepsy. No human data available.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12475725
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
Edited
Mon Mar 31 18:24:41 GMT 2025
by
admin
on
Mon Mar 31 18:24:41 GMT 2025
|
Record UNII |
97CGB1M48I
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
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
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
34301-2
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
34303-8
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
15065-6
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
2266-5
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 |
C2298
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
30508-6
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
82847-5
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
82851-7
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
CFR |
21 CFR 862.1285
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
56488-0
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
82846-7
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
13614-3
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
82881-4
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
82852-5
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
2268-1
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
44355-6
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
82882-2
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
2267-3
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
34302-0
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
80157-1
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
||
|
LOINC |
82853-3
Created by
admin on Mon Mar 31 18:24:41 GMT 2025 , Edited by admin on Mon Mar 31 18:24:41 GMT 2025
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
28195
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 | |||
|
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 | |||
|
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 | |||
|
5880
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 | |||
|
DB02854
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 | |||
|
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 | |||
|
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
|