Etifoxine

Identification

Summary

Etifoxine is a benzoxazine class drug primarily used as an anxiolytic, but that also possesses neuroprotective, neuroplastic, and anti-inflammatory properties; these effects are thought to arise due to modulation of GABAergic neurotransmission and neurosteroid synthesis.

Generic Name
Etifoxine
DrugBank Accession Number
DB08986
Background

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 does not bind to the benzodiazepine receptor though the effects are similar to that of benzodiazepines. It is more effective than lorazepam as an anxiolytic, and has fewer side effects. Etifoxine has been associated with acute liver injury.

Type
Small Molecule
Groups
Investigational, Withdrawn
Structure
Thumb
Weight
Average: 300.79
Monoisotopic: 300.1029409
Chemical Formula
C17H17ClN2O
Synonyms
  • Etifoxina
  • Etifoxine
  • Etifoxinum
External IDs
  • HOE 36801

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Etifoxine is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Etifoxine.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Etifoxine.
AclidiniumEtifoxine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Etifoxine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Etifoxine.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Etifoxine.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Etifoxine.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Etifoxine.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Etifoxine.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Etifoxine hydrochlorideNBL8010WH556776-32-0SCBJXEBIMVRTJE-UHFFFAOYSA-N
International/Other Brands
Exsist (Euroetika) / Stresam (Biocodex)

Categories

ATC Codes
N05BX03 — Etifoxine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Benzoxazine / Hydrocarbon derivative / Isourea / Monocyclic benzene moiety / Organic 1,3-dipolar compound
show 9 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
X24X82MX4X
CAS number
21715-46-8
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

References

Synthesis Reference

U.S. Patent 3,725,404.

General References
Not Available
KEGG Drug
D07320
PubChem Compound
30768
PubChem Substance
310264947
ChemSpider
28547
RxNav
24441
ChEBI
135272
ChEMBL
CHEMBL2106227
Drugs.com
Drugs.com Drug Page
Wikipedia
Etifoxine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedBasic ScienceHealthy Subjects (HS)1
3Unknown StatusBasic ScienceVolunteers Aged Between 65 and 75 Years Old1
Not AvailableRecruitingOtherMultiple Sclerosis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule, coatedOral50 mg
Capsule50 mg
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

Drug created on June 10, 2014 18:03 / Updated on June 02, 2021 20:03