Toloxatone - Misplaced Pages

Antidepressant Pharmaceutical compound

Toloxatone
Clinical data

Routes of administration	Oral
ATC code	N06AG03 (WHO)
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 5-(hydroxymethyl)-3-m-tolyloxazolidin-2-one
CAS Number	29218-27-7
PubChem CID	34521
ChemSpider	31769
UNII	5T206015T5
KEGG	D02559
ChEBI	CHEBI:134870
ChEMBL	ChEMBL18116
CompTox Dashboard (EPA)	DTXSID40865478
ECHA InfoCard	100.045.006
Chemical and physical data
Formula	C₁₁H₁₃NO₃
Molar mass	207.229 g·mol
3D model (JSmol)	Interactive image
SMILES O=C2OC(CO)CN2c1cccc(c1)C
InChI InChI=1S/C11H13NO3/c1-8-3-2-4-9(5-8)12-6-10(7-13)15-11(12)14/h2-5,10,13H,6-7H2,1H3 Key:MXUNKHLAEDCYJL-UHFFFAOYSA-N

Toloxatone (Humoryl) is an antidepressant launched in 1984 in France by Sanofi Aventis for the treatment of depression. It was discontinued in 2002. It acts as a selective reversible inhibitor of MAO-A (RIMA).

Synthesis

The reaction between glycidol (1) and m-toluidine (2) gives 3-m-toluidinopropane-1,2-diol (3). Treatment with diethyl carbonate (4) in the presence of sodium methoxide leads to an intermolecular cycloaddition to give tomoxatone.

References

"Humoryl 200mg gelule 30".
Berlin I, Zimmer R, Thiede HM, et al. (December 1990). "Comparison of the monoamine oxidase inhibiting properties of two reversible and selective monoamine oxidase-A inhibitors moclobemide and toloxatone, and assessment of their effect on psychometric performance in healthy subjects". British Journal of Clinical Pharmacology. 30 (6): 805–16. doi:10.1111/j.1365-2125.1990.tb05445.x. PMC 1368300. PMID 1705137.
Sungurbey, K .; Castaer, J .; Toloxatone. Drugs Fut 1976, 1, 12, 569.
Douzon, C.; Fauvan, C.; Une nouvelle serie d'antidpresseurs: les derivs de l'hydroxymthyl-5-oxazolidinone-2. Chimie Thrapeutique 1973, 3, 324-327.
DE2012120 Claude P Fauran, Guy M Raynaud, Rene A Oliver, Colette A Douzon, U.S. patent 3,655,687 (1972 to Delalande Sa).

Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIsTooltip Selective serotonin reuptake inhibitors	Citalopram Escitalopram Fluoxetine Fluvoxamine Indalpine Paroxetine Sertraline Zimelidine
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine
NRIsTooltip Norepinephrine reuptake inhibitors	Atomoxetine Reboxetine Viloxazine
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors	Amineptine Bupropion Nomifensine
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants	Mianserin Mirtazapine Setiptiline
SARIsTooltip Serotonin antagonist and reuptake inhibitors	Etoperidone Nefazodone Trazodone
SMSTooltip Serotonin modulator and stimulators	Vilazodone Vortioxetine
Others	Agomelatine Amisulpride Dextromethorphan/bupropion Esketamine Etryptamine Gepirone Indeloxazine Flupentixol Ketamine Medifoxamine Metryptamine Oxaflozane Pivagabine Tandospirone Teniloxazine Tianeptine

Tricyclic and tetracyclic antidepressants

TCAsTooltip Tricyclic antidepressants	Amineptine Amitriptyline Amitriptylinoxide Amoxapine Butriptyline Clomipramine Demexiptiline Desipramine Dibenzepin Dimetacrine Dosulepin Doxepin Imipramine Imipraminoxide Iprindole Lofepramine Melitracen Metapramine Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine Protriptyline Quinupramine Tianeptine Trimipramine
TeCAsTooltip Tetracyclic antidepressants	Maprotiline Mianserin Mirtazapine Setiptiline
Others	Tiazesim

Monoamine oxidase inhibitors

Non-selective

Reversible: Caroxazone

Mixed: Bifemelane

MAO_ATooltip Monoamine oxidase A-selective

MAO_BTooltip Monoamine oxidase B-selective

Irreversible: Selegiline

Adjunctive therapies
Atypical antipsychotics (aripiprazole, brexpiprazole, lurasidone, olanzapine, quetiapine, risperidone) Buspirone Lithium (lithium carbonate, lithium citrate) Thyroid hormones (triiodothyronine (T₃), levothyroxine (T₄))

Miscellaneous
Ademetionine (SAMe) GABAkine neurosteroids (brexanolone, zuranolone) Hypericum perforatum (St. John's Wort) Oxitriptan (5-HTP) Rubidium chloride (RbCl) Tryptophan

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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

Monoamine metabolism modulators

Non-specific

AAADTooltip Aromatic L-amino acid decarboxylase

Substrates→Products: L-DOPA (levodopa)→Dopamine
5-HTP→Serotonin
L-Histidine→Histamine
Phenylalanine→Phenethylamine
L-Tyrosine→Tyramine
Tryptophan→Tryptamine

MAOTooltip Monoamine oxidase

Substrates→Products (with ALDHTooltip Aldehyde dehydrogenase/ALRTooltip ALR): Epinephrine (adrenaline)→DHMA
Metanephrine→MHPG/VMA
Norepinephrine (noradrenaline)→DHMA
Normetanephrine→MHPG/VMA
Dopamine→DOPAC
3-Methoxytyramine→HVA
Serotonin→5-HIAA

Inhibitors: Non-selective: Benmoxin
Caroxazone
Echinopsidine
Furazolidone
Guineesine
Hydralazine
Indantadol
Iproclozide
Iproniazid
Isocarboxazid
Isoniazid
Linezolid
Mebanazine
Metfendrazine
Nialamide
Octamoxin
Paraxazone
Phenelzine
Pheniprazine
Phenoxypropazine
Pivhydrazine
Procarbazine
Safrazine
Tranylcypromine

Inhibitors: MAO-A-selective: Amiflamine
Bazinaprine
Befloxatone
Brofaromine
Cimoxatone
Clorgiline
CX157 (Tyrima)
Eprobemide
Esuprone
Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine)
Methylene blue
Metralindole
Minaprine
Moclobemide
Pirlindole
Sercloremine
Tetrindole
Toloxatone

Inhibitors: MAO-B selective: Adarigiline
Almoxatone
D-Deprenyl
Desmethylselegiline
Ethanol
Ladostigil
Lazabemide
Milacemide
Mofegiline
Nicotine
Pargyline
Rasagiline
Safinamide
Selegiline (L-Deprenyl)
Sembragiline
Tisolagiline
Vafidemstat

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAHTooltip Phenylalanine hydroxylase	Substrates→Products: Phenylalanine→Tyrosine Inhibitors: 3,4-Dihydroxystyrene α-Methylphenylalanine
THTooltip Tyrosine hydroxylase	Substrates→Products: Tyrosine→L-DOPA (levodopa) Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine α-Methyl-5-hydroxytryptophan (α-Me-5-HTP) α-Methylphenylalanine Aquayamycin Bulbocapnine Methyldopa (α-methyl-L-DOPA) Metirosine (α-methyl-p-tyrosine) Oudenone
DBHTooltip Dopamine beta-hydroxylase	Substrates→Products: Dopamine→Norepinephrine (Noradrenaline) Inhibitors: Bupicomide Disulfiram Dopastin Etamicastat Fusaric acid Nepicastat Phenopicolinic acid Tropolone Zamicastat
PNMTTooltip Phenylethanolamine N-methyltransferase	Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine (adrenaline) Inhibitors: CGS-19281A SKF-64139 SKF-7698
COMTTooltip Catechol-O-methyl transferase	Substrates→Products: Dopamine→3-Methoxytyramine DOPAC→Homovanillic acid Norepinephrine→Normetanephrine Epinephrine→Metanephrine DOPEG→MOPEG DOMA→VMA 2-Hydroxyestradiol→2-Methoxyestradiol 2-Hydroxyestrone→2-Methoxyestrone 4-Hydroxyestradiol→4-Methoxyestradiol 4-Hydroxyestrone→4-Methoxyestrone Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Nebicapone Neluxicapone Nitecapone Opicapone Quinalizarin Tolcapone

Tryptamines
(serotonin, melatonin)

TPHTooltip Tryptophan hydroxylase

Substrates→Products: Tryptophan→5-HTP

AANATTooltip Serotonin N-acetyl transferase

Substrates→Products: Serotonin→N-Acetylserotonin

ASMTTooltip Acetylserotonin O-methyltransferase

Substrates→Products: N-Acetylserotonin→Melatonin

Histamine

HDCTooltip Histidine decarboxylase

Substrates→Products: L-Histidine→Histamine

HNMTTooltip Histamine N-methyltransferase

Substrates→Products: Histamine→N-Methylhistamine

DAOTooltip Diamine oxidase

Substrates→Products: Histamine→Imidazole acetic acid

Inhibitors: Pimagedine (aminoguanidine)

See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins

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