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- Investigational, Withdrawn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
- Weight
- Average: 300.79
Monoisotopic: 300.1029409 - Chemical Formula
- C17H17ClN2O
- Synonyms
- Etifoxina
- Etifoxine
- Etifoxinum
- External IDs
- HOE 36801
Pharmacology
- Indication
Not Available
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Anxiety •••••••••••• ••••••• - Contraindications & Blackbox Warnings
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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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Etifoxine is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Etifoxine. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Etifoxine. Agomelatine The risk or severity of CNS depression can be increased when Agomelatine is combined with Etifoxine. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Etifoxine. - Food Interactions
- Not Available
Products
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- Product Ingredients
Ingredient UNII CAS InChI Key Etifoxine hydrochloride NBL8010WH5 56776-32-0 SCBJXEBIMVRTJE-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
- External Links
- Human Metabolome Database
- HMDB0252098
- KEGG Drug
- D07320
- PubChem Compound
- 30768
- PubChem Substance
- 310264947
- ChemSpider
- 28547
- 24441
- ChEBI
- 135272
- ChEMBL
- CHEMBL2106227
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Etifoxine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Basic Science Healthy Volunteers (HV) 1 3 Unknown Status Basic Science Volunteers Aged Between 65 and 75 Years Old 1 Not Available Recruiting Other Multiple Sclerosis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule, coated Oral 50 mg Capsule 50 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 90-92 U.S. Patent 3,725,404. - Predicted Properties
Property Value Source Water Solubility 0.00216 mg/mL ALOGPS logP 4.52 ALOGPS logP 4.59 Chemaxon logS -5.1 ALOGPS pKa (Strongest Basic) 5.18 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 33.62 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 87.23 m3·mol-1 Chemaxon Polarizability 32.25 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-1019000000-1b1a9cf675765b21dc68 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-3090000000-a834d964943b9d856654 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udl-5298000000-552349fd00599146237e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9020000000-4574c721662fa54d8ec4 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001l-9100000000-7a7b738e705c3eae5262 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9621000000-2ef4848ee5555cc7317c Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 168.00246 predictedDeepCCS 1.0 (2019) [M+H]+ 170.36044 predictedDeepCCS 1.0 (2019) [M+Na]+ 176.4536 predictedDeepCCS 1.0 (2019)
Drug created at June 10, 2014 18:03 / Updated at March 13, 2024 11:00