Etifoxine

Identification

Name
Etifoxine
Accession Number
DB08986
Type
Small Molecule
Groups
Investigational, Withdrawn
Description

Etifoxine is an anxiolytic and anticonvulsant drug developed by Hoechst in the 1960s. It is used in anxiety disorders and to promote peripheral nerve healing. It has similar effects to benzodiazepine drugs, but is structurally distinct and does not bind to the benzodiazepine receptor. It is more effective than lorazepam as an anxiolytic, and has fewer side effects. Etifoxine has been associated with acute liver injury.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Etifoxine hydrochlorideNBL8010WH556776-32-0SCBJXEBIMVRTJE-UHFFFAOYSA-N
International/Other Brands
Exsist (Euroetika) / Stresam (Biocodex)
Categories
UNII
X24X82MX4X
CAS number
21715-46-8
Weight
Average: 300.79
Monoisotopic: 300.1029409
Chemical Formula
C17H17ClN2O
InChI Key
IBYCYJFUEJQSMK-UHFFFAOYSA-N
InChI
InChI=1S/C17H17ClN2O/c1-3-19-16-20-15-10-9-13(18)11-14(15)17(2,21-16)12-7-5-4-6-8-12/h4-11H,3H2,1-2H3,(H,19,20)
IUPAC Name
6-chloro-N-ethyl-4-methyl-4-phenyl-4H-3,1-benzoxazin-2-amine
SMILES
CCNC1=NC2=CC=C(Cl)C=C2C(C)(O1)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Etifoxine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Etifoxine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Etifoxine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Etifoxine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Etifoxine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Etifoxine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Etifoxine.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Etifoxine.
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Etifoxine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Etifoxine.
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 3,725,404.

General References
Not Available
External Links
KEGG Drug
D07320
PubChem Compound
30768
PubChem Substance
310264947
ChemSpider
28547
ChEBI
135272
ChEMBL
CHEMBL2106227
Drugs.com
Drugs.com Drug Page
Wikipedia
Etifoxine
ATC Codes
N05BX03 — Etifoxine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedBasic ScienceHealthy Volunteers1
3Unknown StatusBasic ScienceVolunteers Aged Between 65 and 75 Years Old1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)90-92U.S. Patent 3,725,404.
Predicted Properties
PropertyValueSource
Water Solubility0.00216 mg/mLALOGPS
logP4.52ALOGPS
logP4.59ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)5.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.62 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity87.23 m3·mol-1ChemAxon
Polarizability32.25 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzoxazines
Sub Class
Not Available
Direct Parent
Benzoxazines
Alternative Parents
Benzene and substituted derivatives / Aryl chlorides / Isoureas / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organochlorides
show 1 more
Substituents
Benzoxazine / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Benzenoid / Isourea / Oxacycle / Azacycle / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound
show 9 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on June 10, 2014 12:03 / Updated on November 02, 2018 09:11