Etifoxine - CAS 21715-46-8
Catalog number:
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
Molecular Weight:
GABA Receptor
Etifoxine, also called as HOE 36801 or Stresam, is a positive allosteric modulator of GABAreceptors that produces anxiolytic effects by preferentially modulating GABAA receptors containing β2 or β3 subunits over those bearing a β1 subunit.
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> 95%
Solid powder
6-chloro-N-ethyl-4-methyl-4-phenyl-3,1-benzoxazin-2-amine 2-ethylamino-6-chloro-4-methyl-4-phenyl-4H-3,1-benzoxazine etafenoxine etafenoxine hydrochloride etifoxin etifoxine etifoxine hydrochloride HOE 36801 Stresam
Soluble in DMSO
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -75℃ for long term (months to years).
Shelf Life:
2 years
Boiling Point:
421.2±55.0 °C | Condition: Press: 760 Torr
Melting Point:
90-92 °C
1.20±0.1 g/cm3
Canonical SMILES:
1.Differential efficacy of the TSPO ligands etifoxine and XBD-173 in two rodent models of Multiple Sclerosis.
Ravikumar B1, Crawford D1, Dellovade T1, Savinainen A1, Graham D1, Liere P2, Oudinet JP2, Webb M1, Hering H3. Neuropharmacology. 2016 Mar 30. pii: S0028-3908(16)30125-3. doi: 10.1016/j.neuropharm.2016.03.053. [Epub ahead of print]
Neurosteroids such as progesterone and allopregnanolone have been shown to exert neuroprotective effects under a variety of pathological or insult conditions, and there is evidence that the neurosteroid system is perturbed in Multiple Sclerosis (MS) patients. Neurosteroids are synthesized in the central nervous system (CNS) through a series of metabolic transformations, beginning with a rate-limiting step of cholesterol transport through the outer mitochondrial membrane via the transporter translocator protein (TSPO). We examined the effects of etifoxine and XBD-173, two different brain penetrant TSPO agonists, for their ability to ameliorate clinical signs in two different experimental autoimmune encephalitis (EAE) models. Etifoxine, as previously reported, was efficacious in EAE, while XBD-173 was not. Surprisingly, XBD-173, but not etifoxine elevated relevant neurosteroids in brain of female rats and differed in its ability to exert anti-inflammatory and direct neuroprotective effects in vitro as compared to etifoxine.
2.Development of a stability-indicating HPLC method of etifoxine with characterization of degradation products by LC-MS/TOF, 1H and 13C NMR.
Djabrouhou N1, Guermouche MH2. J Pharm Biomed Anal. 2014 Nov;100:11-20. doi: 10.1016/j.jpba.2014.07.017. Epub 2014 Jul 27.
This paper describes a new LC-MS/TOF method for the degradation products determination when Etifoxine (ETI) is submitted to different stress conditions. Chromatography is performed by using Kromasil C18 column (250mm×4.6mm, 5μm particle size). The selected mobile phase consists of formate buffer 0.02M, pH 3 and methanol (70/30, v/v). ETI is submitted to oxidative, acidic, basic, hydrolytic, thermal and UV light degradations. Detection is made at 254nm by photodiode array detector and mass spectrometry. A number of degradation products (DPs) called DPA, DPB, DPC and DPD are found depending on the stress; DPA with heat, DPA and DPB in acidic media or under UV-light; DPA, DPB and DPC under basic stress; DPA, DPB, DPC and DPD with oxidation. LC-MS/TOF is used to characterize the four DPs of ETI resulting from different stress conditions. (1)H and (13)C NMR are used to confirm the DP structures. The ETI fragmentation pathway is proposed. The method is validated with reference to International Conference on Harmonization guidelines and ETI are selectively determined in presence of its DPs, demonstrating its stability-indicating nature.
3.Safety profile of etifoxine: A French pharmacovigilance survey.
Cottin J1, Gouraud A1, Jean-Pastor MJ2, Dautriche AD3, Boulay C4, Geniaux H5, Auffret M6, Bernard N1, Descotes J1, Vial T1. Fundam Clin Pharmacol. 2016 Apr;30(2):147-52. doi: 10.1111/fcp.12169. Epub 2016 Jan 26.
Etifoxine chlorhydrate is a benzoxazine derivative approved for the treatment of psychosomatic manifestations of anxiety since 1979. Previously labeled adverse drug reactions (ADRs) only include drowsiness, benign cutaneous reactions, and acute hypersensitivity reactions. The objectives were to examine recent data on etifoxine-related ADR by reviewing Individual Case Safety Reports (ICSRs) recorded in France especially unexpected ADRs. Etifoxine-related ICSRs were extracted from the French Pharmacovigilance database from 1 January 2000 to 30 April 2012 and data from the marketing authorization holder up to 31 December 2011 were also obtained. Of the 350 cases retained for analysis, 123 (35%) were considered serious. Dermatological or acute hypersensitivity reactions were the most frequent ADRs (59%) mainly isolated cutaneous eruptions. However, there were 24 cases of severe toxidermia (DRESS in 5, erythema multiforme in 10 and Stevens-Johnson syndrome in 5) with etifoxine as the most suspected drug in 11 patients, and seven cases of vasculitis or serum sickness-like reaction.
4.Characterization of the fast GABAergic inhibitory action of etifoxine during spinal nociceptive processing in male rats.
Juif PE1, Melchior M1, Poisbeau P2. Neuropharmacology. 2015 Apr;91:117-22. doi: 10.1016/j.neuropharm.2014.12.022. Epub 2014 Dec 26.
Etifoxine (EFX) is a non-benzodiazepine anxiolytic which potentiate GABAA receptor (GABAAR) function directly or indirectly via the production of 3α-reduced neurosteroids. The later effect is now recognized to account for the long-term reduction of pain symptoms in various neuropathic and inflammatory pain models. In the present study, we characterized the acute antinociceptive properties of EFX during spinal pain processing in naive and monoarthritic rats using in vivo electrophysiology. The topical application of EFX on lumbar spinal cord segment, at concentrations higher than 30 μM, reduced the excitability of wide dynamic range neurons receiving non-nociceptive and nociceptive inputs. Windup discharge resulting from the repetitive stimulation of the peripheral receptive field, and recognized as a short-term plastic process seen in central nociceptive sensitization, was significantly inhibited by EFX at these concentrations. In good agreement, mechanical nociceptive thresholds were also significantly increased following an acute intrathecal injection of EFX.
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CAS 21715-46-8 Etifoxine

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