Cimoxatone

Cimoxatone
Clinical data

ATC code	none
Identifiers
IUPAC name 3-[[4-[5-(methoxymethyl)-2-oxo-oxazolidin-3-yl]phenoxy]methyl]benzonitrile
CAS Number	73815-11-9^Y
PubChem (CID)	52542
ChemSpider	47493^Y
UNII	V6FT1QJ7VL^Y
KEGG	D02581^Y
ChEMBL	CHEMBL2104092^N
ECHA InfoCard	100.070.537
Chemical and physical data
Formula	C₁₉H₁₈N₂O₄
Molar mass	338.36 g/mol
InChI InChI=1S/C19H18N2O4/c1-23-13-18-11-21(19(22)25-18)16-5-7-17(8-6-16)24-12-15-4-2-3-14(9-15)10-20/h2-9,18H,11-13H2,1H3^Y Key:MVVJINIUPYKZHR-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Cimoxatone (MD 780515) is a reversible inhibitor of MAO-A (RIMA).^[1] It has a significant food interaction–related adverse effect in combination with tyramine.^[2] It was never marketed.

References

↑ Nair NP, Ahmed SK, Kin NM, West TE (1995). "Reversible and selective inhibitors of monoamine oxidase A in the treatment of depressed elderly patients". Acta Psychiatr Scand Suppl. 386: 28–35. doi:10.1111/j.1600-0447.1995.tb05921.x. PMID 7717092.
↑ Nair NP, Ahmed SK, Kin NM (November 1993). "Biochemistry and pharmacology of reversible inhibitors of MAO-A agents: focus on moclobemide". J Psychiatry Neurosci. 18 (5): 214–25. PMC 1188542. PMID 7905288.

Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIs	Citalopram Escitalopram Fluoxetine^# Fluvoxamine Indalpine^‡ Paroxetine Sertraline Zimelidine^‡

SNRIs	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine

NRIs	Atomoxetine Reboxetine Viloxazine

NDRIs	Amineptine^‡ Bupropion Nomifensine^‡

NaSSAs	Mianserin Mirtazapine Setiptiline

SARIs	Etoperidone Nefazodone^‡ Trazodone

SMSs	Vilazodone Vortioxetine

Others	Agomelatine Amisulpride Amitriptyline/perphenazine Buprenorphine Bupropion Etryptamine^‡ Flupentixol/melitracen Esketamine Ketamine Indeloxazine Lurasidone Medifoxamine^‡ Metryptamine^‡ Olanzapine/fluoxetine Oxaflozane^‡ Quetiapine Tandospirone Teniloxazine Tianeptine Tranylcypromine/trifluoperazine

Tricyclic and tetracyclic antidepressants

TCAs	Amineptine^‡ Amitriptyline^# Amitriptylinoxide Butriptyline^‡ Clomipramine^# Demexiptiline^‡ Desipramine Dibenzepin Dimetacrine^‡ Dosulepin Doxepin Imipramine Imipraminoxide^‡ Iprindole^‡ Lofepramine Melitracen Metapramine^‡ Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine^‡ Protriptyline Quinupramine^‡ Tianeptine Trimipramine

TeCAs	Amoxapine Maprotiline Mianserin Mirtazapine Setiptiline

Others	Tiazesim

Monoamine oxidase inhibitors

Non-selective	Irreversible: Benmoxin^‡ Iproclozide^‡ Iproniazid^‡ Isocarboxazid Mebanazine^‡ Nialamide^‡ Octamoxin^‡ Phenelzine Pheniprazine^‡ Phenoxypropazine^‡ Pivhydrazine^‡ Safrazine^‡ Tranylcypromine Reversible: Caroxazone^‡

MAO_A-selective	Reversible: Bifemelane Eprobemide Metralindole Minaprine^‡ Moclobemide Pirlindole Tetrindole Toloxatone

MAO_B-Selective	Irreversible: Selegiline

Adjunctive therapies

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

Miscellaneous

Ademetionine (SAMe) Hypericum perforatum (St. John's Wort) Oxitriptan (5-HTP) Tryptophan

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Monoamine metabolism modulators

Common
(non-specific)

AAAD

MAO

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: Almoxatone D-Deprenyl Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl)

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAH	Inhibitors: 3,4-Dihydroxystyrene

TH	Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

DBH	Inhibitors: Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone

PNMT	Inhibitors: CGS-19281A SKF-64139 SKF-7698

COMT	Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Nitecapone Tolcapone

Tryptamines
(serotonin, melatonin)

TPH	Inhibitors: AGN-2979 Fenclonine (PCPA) Telotristat

See also: Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake and release modulators • Monoamine neurotoxins

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