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Systematic (IUPAC) name
6-chloro-N-ethyl-4-methyl-4-phenyl- 4H-benzo[d][1,3]oxazin-2-amine
Clinical data
  • Not recommended. Crosses the placental barrier
Routes of
Pharmacokinetic data
Bioavailability 90%
Metabolism Hepatic (no CYP450 interactions)[1]
Biological half-life 2 to 6 hours (etifoxine), 20 to 30 hours (active metabolite)[2]
Excretion Renal[1]
CAS Number 21715-46-8
ATC code N05BX03 (WHO)
PubChem CID 30768
Chemical data
Formula C17H17ClN2O
Molar mass 300.782 g/mol[[Script error: No such module "String".]]
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Etifoxine (INN, also known as etafenoxine; trade name Stresam) is an anxiolytic and anticonvulsant drug.[3] It is used in anxiety disorders and to promote peripheral nerve healing.[4] It has similar effects to benzodiazepine drugs, but is structurally distinct and so is classed as a nonbenzodiazepine anxiolytic.[5] It is more effective than lorazepam as an anxiolytic, and has fewer side effects.[6]

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

Mechanism of action

Unlike benzodiazepines, etifoxine appears to produce its anxiolytic effects by binding to β2 and β3 subunits of the GABAA 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.[7] This difference in binding means that etifoxine can be used alongside benzodiazepines to potentiate their effects without competing for binding sites,[8] however it also means that the effects of etifoxine are not reversed by the benzodiazepine antagonist flumazenil.[9]


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  • The Merck Index, 12th Edition. 3910
fr:Étifoxine ru:этифоксин
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  2. "Stresam PI" (PDF). Adcock Ingram. n.d. Retrieved 2008-08-30. 
  3. Kruse HJ, Kuch H. Etifoxine: evaluation of its anticonvulsant profile in mice in comparison with sodium valproate, phenytoin and clobazam. Arzneimittelforschung. 1985;35(1):133-5.
  4. Etifoxine improves peripheral nerve regeneration and functional recovery
  5. Schlichter R, Rybalchenko V, Poisbeau P, Verleye M, Gillardin J. Modulation of GABAergic synaptic transmission by the non-benzodiazepine anxiolytic etifoxine. Neuropharmacology. 2000 Jul 10;39(9):1523-35.
  6. Nguyen N, Fakra E, Pradel V, Jouve E, Alquier C, Le Guern ME, Micallef J, Blin O. Efficacy of etifoxine compared to lorazepam monotherapy in the treatment of patients with adjustment disorders with anxiety: a double-blind controlled study in general practice. Human Psychopharmacology. 2006 Apr;21(3):139-49.
  7. Hamon A, Morel A, Hue B, Verleye M, Gillardin JM. The modulatory effects of the anxiolytic etifoxine on GABA(A) receptors are mediated by the beta subunit. Neuropharmacology. 2003 Sep;45(3):293-303.
  8. Kruse HJ, Kuch H. Potentiation of clobazam's anticonvulsant activity by etifoxine, a non-benzodiazepine tranquilizer, in mice. Comparison studies with sodium valproate. Arzneimittelforschung. 1986 Sep;36(9):1320-2.
  9. Verleye M, Schlichter R, Gillardin JM. Interactions of etifoxine with the chloride channel coupled to the GABA(A) receptor complex. Neuroreport. 1999 Oct 19;10(15):3207-10.