Movatterモバイル変換

[0]ホーム

Jump to content

Toloxatone

Edit links

From Wikipedia, the free encyclopedia

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^Y
PubChemCID	34521
ChemSpider	31769^Y
UNII	5T206015T5
KEGG	D02559^Y
ChEBI	CHEBI:134870
ChEMBL	ChEMBL18116^Y
CompTox Dashboard(EPA)	DTXSID40865478
ECHA InfoCard	100.045.006
Chemical and physical data
Formula	C₁₁H₁₃NO₃
Molar mass	207.229 g·mol⁻¹
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^Y Key:MXUNKHLAEDCYJL-UHFFFAOYSA-N^Y

Toloxatone (Humoryl) is anantidepressant launched in 1984 in France bySanofi Aventis for the treatment ofdepression. It was discontinued in 2002.^[1] It acts as a selectivereversible inhibitor of MAO-A (RIMA).^[2]

Synthesis

[edit]

The reaction betweenglycidol (1) andm-toluidine (2) gives 3-m-toluidinopropane-1,2-diol (3). Treatment withdiethyl carbonate (4) in the presence of sodium methoxide leads to an intermolecular cycloaddition to give tomoxatone.^[3]^[4]^[5]

References

[edit]

^"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)

Specificreuptake inhibitors orreceptor 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 andtetracyclic 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	Irreversible:Benmoxin^‡ Iproclozide^‡ Iproniazid^‡ Isocarboxazid Isoniazid^# Linezolid^# Mebanazine^‡ Nialamide^‡ Octamoxin^‡ Phenelzine Pheniprazine^‡ Phenoxypropazine^‡ Pivhydrazine^‡ Safrazine^‡ Tedizolid Tranylcypromine Reversible:Caroxazone^‡ Mixed:Bifemelane
MAO_ATooltip Monoamine oxidase A-selective	Reversible:Eprobemide Metralindole Minaprine^‡ Moclobemide Pirlindole Tetrindole Toloxatone
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 receptoragonists	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
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
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g.,prazosin) Alpha-2 agonists (e.g.,clonidine,dexmedetomidine,guanfacine) Beta blockers (e.g.,propranolol,atenolol,betaxolol,nadolol,oxprenolol,pindolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine (tobacco) 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,6-methoxyharman) 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 Inhibitors:AGN-2979 Fenclonine (PCPA) Telotristat ethyl
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 Inhibitors:Catechin Alpha-Fluoromethylhistidine Histidine methyl ester Meciadanol Naringenin Tritoqualine
HNMTTooltip Histamine N-methyltransferase	Substrates→Products:Histamine→N-Methylhistamine Inhibitors:Amodiaquine Diphenhydramine Harmaline Metoprine Quinacrine SKF-91488 Tacrine
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

Thisdrug article relating to thenervous system is astub. You can help Wikipedia byexpanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Toloxatone&oldid=1247273799"

Categories:

Hidden categories:

[8]ページ先頭