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MedKoo Cat#: 576347 | Name: Etifoxine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Etifoxine is a positive allosteric modulator of α1β2γ2 and α1β3γ2 subunit-containing GABAA receptors.

Chemical Structure

Etifoxine
Etifoxine
CAS#21715-46-8 (free base)

Theoretical Analysis

MedKoo Cat#: 576347

Name: Etifoxine

CAS#: 21715-46-8 (free base)

Chemical Formula: C17H17ClN2O

Exact Mass: 300.1029

Molecular Weight: 300.79

Elemental Analysis: C, 67.88; H, 5.70; Cl, 11.79; N, 9.31; O, 5.32

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 1,050.00 2 Weeks
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Related CAS #
21715-46-8 (free base) 56776-32-0 (HCl)
Synonym
Etifoxine; Etafenoxine; Etifoxin; Etifoxina; Etifoxinum; HOE 36801; HOE-36801; HOE36801; HOE 36-801
IUPAC/Chemical Name
6-chloro-N-ethyl-4-methyl-4-phenyl-4H-3, 1-benzoxazin-2-amine
InChi Key
IBYCYJFUEJQSMK-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
CCNC(OC1(C2=CC=CC=C2)C)=NC3=C1C=C(Cl)C=C3
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Etifoxine, a non-benzodiazepine GABAergic compound, is a positive allosteric modulator of α1β2γ2 and α1β3γ2 subunit-containing GABAA receptors.
In vitro activity:
In neuronal cultures intoxicated with Aβ1-42, etifoxine dose-dependently decreased oxidative stress (methionine sulfoxide positive neurons), tau-hyperphosphorylation and synaptic loss (ratio PSD95/synaptophysin). Reference: CNS Neurol Disord Drug Targets. 2020;19(3):227-240. https://pubmed.ncbi.nlm.nih.gov/32479250/
In vivo activity:
The intraperitoneal EFX (etifoxine) treatment for five consecutive days (50 mg/kg) relieved mechanical allodynia in a sustained manner. Besides its effect on evoked mechanical hypersensitivity, EFX also alleviated aversiveness of ongoing pain as well as anxiodepressive-like consequences of neuropathic pain following cuff-induced mononeuropathy. This study suggests that EFX presents promising therapeutic potential for the relief of both somatosensory and affective consequences of neuropathic pain, a beneficial effect that is likely to involve monoamine descending controls. Reference: Neuropharmacology. 2021 Jan;182:108407. https://pubmed.ncbi.nlm.nih.gov/33212115/
Solvent mg/mL mM
Solubility
DMSO 60.0 199.47
DMF 30.0 99.74
DMF:PBS (pH 7.2) (1:8) 0.1 0.33
Ethanol 20.0 66.49
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 300.79 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Riban V, Meunier J, Buttigieg D, Villard V, Verleye M. In Vitro and In Vivo Neuroprotective Effects of Etifoxine in β-Amyloidinduced Toxicity Models. CNS Neurol Disord Drug Targets. 2020;19(3):227-240. doi: 10.2174/1871527319666200601151007. PMID: 32479250. 2. Kokova VY, Zagorchev PI, Apostolova EG, Peychev LP. Etifoxine does not impair muscle tone and motor function in rats as assessed by in vivo and in vitro methods. Gen Physiol Biophys. 2020 Mar;39(2):179-186. doi: 10.4149/gpb_2019053. PMID: 32329445. 3. Kamoun N, Gazzo G, Goumon Y, Andry V, Yalcin I, Poisbeau P. Long-lasting analgesic and neuroprotective action of the non-benzodiazepine anxiolytic etifoxine in a mouse model of neuropathic pain. Neuropharmacology. 2021 Jan;182:108407. doi: 10.1016/j.neuropharm.2020.108407. Epub 2020 Nov 16. PMID: 33212115. 4. Zhang H, Ma L, Guo WZ, Jiao LB, Zhao HY, Ma YQ, Hao XM. TSPO ligand etifoxine attenuates LPS-induced cognitive dysfunction in mice. Brain Res Bull. 2020 Dec;165:178-184. doi: 10.1016/j.brainresbull.2020.10.013. Epub 2020 Oct 16. PMID: 33075418.
In vitro protocol:
1. Riban V, Meunier J, Buttigieg D, Villard V, Verleye M. In Vitro and In Vivo Neuroprotective Effects of Etifoxine in β-Amyloidinduced Toxicity Models. CNS Neurol Disord Drug Targets. 2020;19(3):227-240. doi: 10.2174/1871527319666200601151007. PMID: 32479250. 2. Kokova VY, Zagorchev PI, Apostolova EG, Peychev LP. Etifoxine does not impair muscle tone and motor function in rats as assessed by in vivo and in vitro methods. Gen Physiol Biophys. 2020 Mar;39(2):179-186. doi: 10.4149/gpb_2019053. PMID: 32329445.
In vivo protocol:
1. Kamoun N, Gazzo G, Goumon Y, Andry V, Yalcin I, Poisbeau P. Long-lasting analgesic and neuroprotective action of the non-benzodiazepine anxiolytic etifoxine in a mouse model of neuropathic pain. Neuropharmacology. 2021 Jan;182:108407. doi: 10.1016/j.neuropharm.2020.108407. Epub 2020 Nov 16. PMID: 33212115. 2. Zhang H, Ma L, Guo WZ, Jiao LB, Zhao HY, Ma YQ, Hao XM. TSPO ligand etifoxine attenuates LPS-induced cognitive dysfunction in mice. Brain Res Bull. 2020 Dec;165:178-184. doi: 10.1016/j.brainresbull.2020.10.013. Epub 2020 Oct 16. PMID: 33075418.
1: Choi YM, Kim KH. Etifoxine for pain patients with anxiety. Korean J Pain. 2015 Jan;28(1):4-10. doi: 10.3344/kjp.2015.28.1.4. Epub 2015 Jan 2. PMID: 25589941; PMCID: PMC4293506. 2: Tian Q, Yang X, Du J, Huang H, Liu W, Zhao P. Translocator Protein Ligand Etifoxine Attenuates MPTP-Induced Neurotoxicity. Front Mol Neurosci. 2022 May 24;15:850904. doi: 10.3389/fnmol.2022.850904. PMID: 35686060; PMCID: PMC9172994. 3: Zhang H, Ma L, Guo WZ, Jiao LB, Zhao HY, Ma YQ, Hao XM. TSPO ligand etifoxine attenuates LPS-induced cognitive dysfunction in mice. Brain Res Bull. 2020 Dec;165:178-184. doi: 10.1016/j.brainresbull.2020.10.013. Epub 2020 Oct 16. PMID: 33075418. 4: Poisbeau P, Gazzo G, Calvel L. Anxiolytics targeting GABAA receptors: Insights on etifoxine. World J Biol Psychiatry. 2018;19(sup1):S36-S45. doi: 10.1080/15622975.2018.1468030. PMID: 30204559. 5: Palzur E, Edelman D, Sakas R, Soustiel JF. Etifoxine Restores Mitochondrial Oxidative Phosphorylation and Improves Cognitive Recovery Following Traumatic Brain Injury. Int J Mol Sci. 2021 Nov 28;22(23):12881. doi: 10.3390/ijms222312881. PMID: 34884686; PMCID: PMC8657969. 6: Nuss P, Ferreri F, Bourin M. An update on the anxiolytic and neuroprotective properties of etifoxine: from brain GABA modulation to a whole-body mode of action. Neuropsychiatr Dis Treat. 2019 Jul 3;15:1781-1795. doi: 10.2147/NDT.S200568. PMID: 31308671; PMCID: PMC6615018. 7: Ibrahim KS, Craft JA, Biswas L, Spencer J, Shu X. Etifoxine reverses weight gain and alters the colonic bacterial community in a mouse model of obesity. Biochem Pharmacol. 2020 Oct;180:114151. doi: 10.1016/j.bcp.2020.114151. Epub 2020 Jul 15. PMID: 32679124. 8: Kokova VY, Zagorchev PI, Apostolova EG, Peychev LP. Etifoxine does not impair muscle tone and motor function in rats as assessed by in vivo and in vitro methods. Gen Physiol Biophys. 2020 Mar;39(2):179-186. doi: 10.4149/gpb_2019053. PMID: 32329445. 9: Dai T, Zhou X, Li Y, He B, Zhu Z, Zheng C, Zhu S, Zhu Q, Liu X. Etifoxine promotes glia-derived neurite outgrowth in vitro and in vivo. J Reconstr Microsurg. 2014 Jul;30(6):381-8. doi: 10.1055/s-0034-1381751. Epub 2014 Jun 23. PMID: 24956483. 10: Owen DR, Phillips A, O'Connor D, Grey G, Aimola L, Nicholas R, Matthews PM. Human pharmacokinetics of XBD173 and etifoxine distinguish their potential for pharmacodynamic effects mediated by translocator protein. Br J Clin Pharmacol. 2022 Sep;88(9):4230-4236. doi: 10.1111/bcp.15392. Epub 2022 May 20. PMID: 35524344; PMCID: PMC9545781. 11: Zhou X, He X, He B, Zhu Z, Zheng C, Xu J, Jiang L, Gu L, Zhu J, Zhu Q, Liu X. Etifoxine promotes glial‑derived neurotrophic factor‑induced neurite outgrowth in PC12 cells. Mol Med Rep. 2013 Jul;8(1):75-80. doi: 10.3892/mmr.2013.1474. Epub 2013 May 13. PMID: 23670018. 12: Vicente B, Saldivia S, Hormazabal N, Bustos C, Rubí P. Etifoxine is non- inferior than clonazepam for reduction of anxiety symptoms in the treatment of anxiety disorders: a randomized, double blind, non-inferiority trial. Psychopharmacology (Berl). 2020 Nov;237(11):3357-3367. doi: 10.1007/s00213-020-05617-6. Epub 2020 Oct 2. PMID: 33009629. 13: Riebel M, von Pappenheim B, Kanig C, Nothdurfter C, Wetter TC, Rupprecht R, Schwarzbach J. GABAergic Effects of Etifoxine and Alprazolam Assessed by Double Pulse TMS. Pharmacopsychiatry. 2023 Jul;56(4):154-161. doi: 10.1055/a-2078-4823. Epub 2023 May 23. PMID: 37220781. 14: Deplanque D, Machuron F, Waucquier N, Jozefowicz E, Duhem S, Somers S, Colin O, Duhamel A, Bordet R. Etifoxine impairs neither alertness nor cognitive functions of the elderly: A randomized, double-blind, placebo-controlled crossover study. Eur Neuropsychopharmacol. 2018 Aug;28(8):925-932. doi: 10.1016/j.euroneuro.2018.05.011. Epub 2018 Jun 29. PMID: 30135030. 15: Stein DJ. Etifoxine versus alprazolam for the treatment of adjustment disorder with anxiety: a randomized controlled trial. Adv Ther. 2015 Jan;32(1):57-68. doi: 10.1007/s12325-015-0176-6. Epub 2015 Jan 27. PMID: 25620535; PMCID: PMC4311065. 16: Moch C, Rocher F, Lainé P, Lacotte J, Biour M, Gouraud A, Bernard N, Descotes J, Vial T. Etifoxine-induced acute hepatitis: a case series. Clin Res Hepatol Gastroenterol. 2012 Oct;36(5):e85-8. doi: 10.1016/j.clinre.2012.04.002. Epub 2012 May 23. PMID: 22633197. 17: Simon-O'Brien E, Gauthier D, Riban V, Verleye M. Etifoxine improves sensorimotor deficits and reduces glial activation, neuronal degeneration, and neuroinflammation in a rat model of traumatic brain injury. J Neuroinflammation. 2016 Aug 26;13(1):203. doi: 10.1186/s12974-016-0687-3. PMID: 27565146; PMCID: PMC5002207. 18: Cottin J, Gouraud A, Jean-Pastor MJ, Dautriche AD, Boulay C, Geniaux H, Auffret M, Bernard N, Descotes J, Vial T. Safety profile of etifoxine: A French pharmacovigilance survey. Fundam Clin Pharmacol. 2016 Apr;30(2):147-52. doi: 10.1111/fcp.12169. Epub 2016 Jan 26. PMID: 26588183. 19: Lin YM, Sun HY, Chiu WT, Su HC, Chien YC, Chang HA, Chong LW, Chang HC, Young KC, Bai CH, Tsao CW. Etifoxine, a TSPO Ligand, Worsens Hepatitis C-Related Insulin Resistance but Relieves Lipid Accumulation. Biomed Res Int. 2019 Mar 11;2019:3102414. doi: 10.1155/2019/3102414. PMID: 30984779; PMCID: PMC6432734. 20: Gazzo G, Girard P, Kamoun N, Verleye M, Poisbeau P. Analgesic and anti- edemic properties of etifoxine in models of inflammatory sensitization. Eur J Pharmacol. 2019 Jan 15;843:316-322. doi: 10.1016/j.ejphar.2018.12.018. Epub 2018 Dec 12. PMID: 30552900.