Etifoxine

Title: Etifoxine
CAS Registry Number: 21715-46-8
CAS Name: 6-Chloro-N-ethyl-4-methyl-4-phenyl-4H-3,1-benzoxazin-2-amine
Additional Names: 6-chloro-2-(ethylamino)-4-methyl-4-phenyl-4H-3,1-benzoxazine
Manufacturers' Codes: HOE-36801
Molecular Formula: C17H17ClN2O
Molecular Weight: 300.78
Percent Composition: C 67.88%, H 5.70%, Cl 11.79%, N 9.31%, O 5.32%
Literature References: Psychotropic agent with anxiolytic and anticonvulsant activity. Prepn: FR M7358; H. Kuch et al., US 3725404 (1969, 1973 both to Hoechst); I. Hoffmann et al., Arzneim.-Forsch. 20, 975 (1970). Exptl psychopharmacological study: J. R. Boissier et al., Therapie 27, 325 (1972). Analysis of EEG effects: D. Bente et al., Arzneim.-Forsch. 25, 944 (1975). Evaluation of psychotropic effect: R. Corsico et al., Psychopharmacologia 45, 301 (1976).
Properties: Colorless crystals from petr ether, mp 90-92°. uv max (ethanol): 273 nm (e 21200). LD50 orally in mice: 12 g/kg (Hoffmann).
Melting point: mp 90-92°
Absorption maximum: uv max (ethanol): 273 nm (e 21200)
Toxicity data: LD50 orally in mice: 12 g/kg (Hoffmann)
Derivative Type: Hydrochloride
CAS Registry Number: 56776-32-0
Trademarks: Stresam (Beaufour)
Molecular Formula: C17H17ClN2O.HCl
Molecular Weight: 337.24
Percent Composition: C 60.54%, H 5.38%, Cl 21.03%, N 8.31%, O 4.74%
Properties: Crystals, mp 150-151°.
Melting point: mp 150-151°
Therap-Cat: Anxiolytic.
Keywords: Anxiolytic.
Etilefrin Etiocholane Etiocholanic Acid Etiocobalamin Etioporphyrin

Etifoxine
Etifoxine.svg
Etifoxine ball-and-stick.png
Systematic (IUPAC) name
6-chloro-N-ethyl-4-methyl-4-phenyl- 4H-benzo[d][1,3]oxazin-2-amine
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat. Not recommended. Crosses the placental barrier
Legal status  ?
Routes Oral
Pharmacokinetic data
Bioavailability 90%
Metabolism Hepatic (no CYP450 interactions)[1]
Half-life 2 to 6 hours (etifoxine), 20 to 30 hours (active metabolite)[2]
Excretion Renal[1]
Identifiers
CAS number 21715-46-8 YesY
ATC code N05BX03
PubChem CID 30768
ChemSpider 28547 YesY
UNII X24X82MX4X YesY
KEGG D07320 YesY
ChEMBL CHEMBL2106227 N
Chemical data
Formula C17H17ClN2O 
Mol. mass 300.782 g/mol
 N (what is this?)  (verify)

Etifoxine (INN,[3] also known as etafenoxine; trade name Stresam) is an anxiolytic and anticonvulsant drug[4] developed by Hoechst in the 1960s.[3] It is used in anxiety disorders and to promote peripheral nerve healing.[5] It has similar effects to benzodiazepine drugs, but is structurally distinct and does not bind to the benzodiazepine receptor.[6] It is more effective than lorazepam as an anxiolytic, and has fewer side effects.[7]

Etifoxine has been associated with acute liver injury.[1]