Etifoxine

Etifoxine

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 category	Not recommended. Crosses the placental barrier
Legal status	US: Not FDA approved; unscheduled
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	90%
Metabolism	Hepatic (no CYP450 interactions)
Biological half-life	2 to 6 hours (etifoxine), 20 to 30 hours (active metabolite)
Excretion	Renal
Identifiers
CAS Number	21715-46-8 Y
ATC code	N05BX03 (WHO)
PubChem	CID: 30768
IUPHAR/BPS	5468
DrugBank	DB08986 N
ChemSpider	28547 Y
UNII	X24X82MX4X Y
KEGG	D07320 Y
ChEMBL	CHEMBL2106227 N
Chemical data
Formula	C17H17ClN2O
Molecular mass	300.782 g/mol
SMILES ClC1=CC=C2N=C(NCC)OC(C3=CC=CC=C3)(C)C2=C1
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) Y Key:IBYCYJFUEJQSMK-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Etifoxine (INN, also known as etafenoxine; trade name Stresam) is an anxiolytic and anticonvulsant drug developed by Hoechst in the 1960s. It is used in some countries for anxiety disorders. 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 is not approved by the U.S. Food and Drug Administration or the European Medicines Agency.

Side effects

Etifoxine has been associated with acute liver injury.

Mechanism of action

Unlike benzodiazepines, etifoxine appears to produce its anxiolytic effects by binding to β2 and β3 subunits of the GABA_A receptor complex, and so is acting at a different target site to benzodiazepines, although the physiological effect that is produced is similar to that of benzodiazepines. This difference in binding means that etifoxine can be used alongside benzodiazepines to potentiate their effects without competing for binding sites; however, it also means that the effects of etifoxine are not reversed by the benzodiazepine antagonist flumazenil.