Fabomotizole

Fabomotizole
Clinical data
Trade names	Afobazole
Other names	Obenoxazine
Routes of; administration	Oral
Legal status
Legal status	US: Unscheduled Not FDA approved;
Pharmacokinetic data
Bioavailability	43.64%, pronounced first-pass effect
Metabolism	extensive hepatic
Onset of action	0.85±0.13 hours
Elimination half-life	0.82±0.54 hours
Identifiers
	IUPAC name 4-(6-ethoxy-1H-benzimidazol-2-yl)sulfanylethylmorpholine;
CAS Number	173352-21-1;
PubChem CID	9862937;
DrugBank	DB13623;
ChemSpider	8038633;
UNII	0F8K1X115C;
KEGG	D10561;
ChEBI	CHEBI:135309;
ChEMBL	ChEMBL3707307;
CompTox Dashboard (EPA)	DTXSID00169606 ;
Chemical and physical data
Formula	C15H21N3O2S
Molar mass	307.41 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOc3ccc2nc(SCCN1CCOCC1)nHc2c3;
	InChI InChI=1S/C15H21N3O2S/c1-2-20-12-3-4-13-14(11-12)17-15(16-13)21-10-7-18-5-8-19-9-6-18/h3-4,11H,2,5-10H2,1H3,(H,16,17) ; Key:WWNUCVSRRUDYPP-UHFFFAOYSA-N ;
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Fabomotizole (INN;^[1] brand name Afobazole) is an anxiolytic drug launched in Russia in the early 2000s. It produces anxiolytic and neuroprotective effects without any sedative or muscle relaxant actions.^{[citation needed]} Its mechanism of action remains poorly defined however, with GABAergic, NGF- and BDNF-release-promoting, MT1 receptor agonism, MT3 receptor antagonism, and sigma agonism suggested as potential mechanisms. Fabomotizole was shown to inhibit MAO-A reversibly and there might be also some involvement with serotonin receptors.^[2]^[3]^[4]^[5]^[6] Clinical trials have shown fabomotizole to be well tolerated and reasonably effective for the treatment of anxiety.^[7]

Experiments of mice have shown antimutagenic and antiteratogenic properties.^[8]

Fabomotizole has found little clinical use outside Russia and has not been evaluated by the FDA.

Referencesedit

^ "International Nonproprietary Names for Pharmaceutical Substances (INN)" (PDF). WHO Drug Information. 26 (1): 63. 2012. Retrieved 21 March 2015.
^ Neznamov GG, Siuniakov SA, Chumakov DV, Bochkarev VK, Seredenin SB (2001). "Clinical study of the selective anxiolytic agent afobazol". Eksperimental'naia i Klinicheskaia Farmakologiia. 64 (2): 15–19. PMID 11548440.
^ Silkina IV, Gan'shina TC, Seredin SB, Mirzoian RS (2005). "Gabaergic mechanism of cerebrovascular and neuroprotective effects of afobazole and picamilon". Eksperimental'naia i Klinicheskaia Farmakologiia. 68 (1): 20–24. PMID 15786959.
^ Seredin SB, Melkumian DS, Val'dman EA, Iarkova MA, Seredina TC, Voronin MV, Lapitskaia AS (2006). "Effects of afobazole on the BDNF content in brain structures of inbred mice with different phenotypes of emotional stress reaction". Eksperimental'naia i Klinicheskaia Farmakologiia. 69 (3): 3–6. PMID 16878488.
^ Antipova TA, Sapozhnikova DS, Bakhtina LI, Seredenin SB (2009). "Selective anxiolytic afobazole increases the content of BDNF and NGF in cultured hippocampal HT-22 line neurons". Eksperimental'naia i Klinicheskaia Farmakologiia. 72 (1): 12–14. PMID 19334503.
^ Seredenin SB, Antipova TA, Voronin MV, Kurchashova SY, Kuimov AN (July 2009). "Interaction of afobazole with sigma1-receptors". Bulletin of Experimental Biology and Medicine. 148 (1): 42–44. doi:10.1007/s10517-009-0624-x. PMID 19902093. S2CID 37411324.
^ Medvedev VE, Trosnova AP, Dobrovol'skiĭ AV (2007). "Psychopharmacotherapy of anxiety disorders in patients with cardio-vascular diseases: the use of aphobazole". Zhurnal Nevrologii I Psikhiatrii Imeni S.S. Korsakova. 107 (7): 25–29. PMID 18379478.
^ Durnev AD, Zhanataev AK, Shreder OV, Seredenin SB (Jan–Feb 2009). "Antimutagenic and antiteratogenic properties of afobazole". Eksperimental'naia i Klinicheskaia Farmakologiia. 72 (1): 46–51. PMID 19334511.

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[1] "International Nonproprietary Names for Pharmaceutical Substances (INN)" (PDF). WHO Drug Information. 26 (1): 63. 2012. Retrieved 21 March 2015.

[2] Neznamov GG, Siuniakov SA, Chumakov DV, Bochkarev VK, Seredenin SB (2001). "Clinical study of the selective anxiolytic agent afobazol". Eksperimental'naia i Klinicheskaia Farmakologiia. 64 (2): 15–19. PMID 11548440.

[3] Silkina IV, Gan'shina TC, Seredin SB, Mirzoian RS (2005). "Gabaergic mechanism of cerebrovascular and neuroprotective effects of afobazole and picamilon". Eksperimental'naia i Klinicheskaia Farmakologiia. 68 (1): 20–24. PMID 15786959.

[4] Seredin SB, Melkumian DS, Val'dman EA, Iarkova MA, Seredina TC, Voronin MV, Lapitskaia AS (2006). "Effects of afobazole on the BDNF content in brain structures of inbred mice with different phenotypes of emotional stress reaction". Eksperimental'naia i Klinicheskaia Farmakologiia. 69 (3): 3–6. PMID 16878488.

[5] Antipova TA, Sapozhnikova DS, Bakhtina LI, Seredenin SB (2009). "Selective anxiolytic afobazole increases the content of BDNF and NGF in cultured hippocampal HT-22 line neurons". Eksperimental'naia i Klinicheskaia Farmakologiia. 72 (1): 12–14. PMID 19334503.

[6] Seredenin SB, Antipova TA, Voronin MV, Kurchashova SY, Kuimov AN (July 2009). "Interaction of afobazole with sigma1-receptors". Bulletin of Experimental Biology and Medicine. 148 (1): 42–44. doi:10.1007/s10517-009-0624-x. PMID 19902093. S2CID 37411324.

[7] Medvedev VE, Trosnova AP, Dobrovol'skiĭ AV (2007). "Psychopharmacotherapy of anxiety disorders in patients with cardio-vascular diseases: the use of aphobazole". Zhurnal Nevrologii I Psikhiatrii Imeni S.S. Korsakova. 107 (7): 25–29. PMID 18379478.

[8] Durnev AD, Zhanataev AK, Shreder OV, Seredenin SB (Jan–Feb 2009). "Antimutagenic and antiteratogenic properties of afobazole". Eksperimental'naia i Klinicheskaia Farmakologiia. 72 (1): 46–51. PMID 19334511.

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v t e Anxiolytics (N05B)
5-HT_1ARTooltip 5-HT1A receptor agonists	Buspirone Gepirone Tandospirone
GABA_ARTooltip GABAA receptor PAMsTooltip positive allosteric modulators	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone^‡ Ethanol (alcohol) Etifoxine
Hypnotics	Zopiclone
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., escitalopram) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine) SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone) TCAsTooltip Tricyclic antidepressants (e.g., clomipramine^#) TeCAsTooltip Tetracyclic antidepressants (e.g., mirtazapine) MAOIsTooltip Monoamine oxidase inhibitors (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Antipsychotics	Quetiapine Flupentixol
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

v t e Melatonin receptor modulators
MT₁Tooltip Melatonin receptor 1	Agonists: 2-Iodomelatonin 6-Hydroxymelatonin Agomelatine Fabomotizole (afobazole) GR-196,429 Melatonin N-Acetylserotonin (normelatonin) Piromelatine Ramelteon Tasimelteon TIK-301 (LY-156,735) Antagonists: Luzindole
MT₂Tooltip Melatonin receptor 2	Agonists: 2-Iodomelatonin 6-Hydroxymelatonin Agomelatine GR-196,429 Melatonin N-Acetylserotonin (normelatonin) Piromelatine Ramelteon Tasimelteon TIK-301 (LY-156,735) Antagonists: Luzindole
Unsorted	Agonists: 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin 8-M-PDOT AMMTC GR-135,531 (of MT₃Tooltip melatonin receptor 1C) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin S-24268 S-25150 Antagonists: 4-P-ADOT 4-P-PDOT DH-97 N-Acetyltryptamine (of MT₃) Prazosin (of MT₃) S-20928 S-22153 S-24601 S-25567 S-26131
See also: Receptor/signaling modulators Adrenergics Dopaminergics Serotonergics Monoamine metabolism modulators

v t e Sigma receptor modulators
σ₁	Agonists: 3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRPTooltip Calcitonin gene-related peptide Cloperastine Cocaine Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan (DXM) Dextrorphan (DXO) Dimemorfan Dimethyltryptamine (DMT) Ditolylguanidine (DTG) Donepezil Eliprodil Escitalopram Fabomotizole (afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine (JO-1784) IPAB Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) UMB-23 UMB-82 Antagonists: 3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 Dup-734 E-5842 E-52862 (S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine (EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam SOMCL-668 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A
σ₂	Agonists: 3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) UKH-1114 Antagonists: AC-927 BD-1008 BD-1067 CM-156 CT-1812 LR-172 MIN-101 Panamesine (EMD-57455) SAS-0132 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMATooltip 3,4,5-Trimethoxyamphetamine UMB-23 UMB-82 W-18
Unsorted	Agonists: Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists: AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allosteric modulators: SKF-83959 Unknown/unsorted: 18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine
See also: Receptor/signaling modulators

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