Nialamide

Nialamide
Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	N06AF02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)
Identifiers
IUPAC name N-benzyl-3-(N'-(pyridine-4-carbonyl)hydrazino)propanamide
CAS Number	51-12-7^Y
PubChem (CID)	4472
DrugBank	DB04820^Y
ChemSpider	4317^Y
UNII	T2Q0RYM725^Y
KEGG	D07337^Y
ECHA InfoCard	100.000.073
Chemical and physical data
Formula	C₁₆H₁₈N₄O₂
Molar mass	298.34 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(NNCCC(=O)NCc1ccccc1)c2ccncc2
InChI InChI=1S/C16H18N4O2/c21-15(18-12-13-4-2-1-3-5-13)8-11-19-20-16(22)14-6-9-17-10-7-14/h1-7,9-10,19H,8,11-12H2,(H,18,21)(H,20,22)^Y Key:NOIIUHRQUVNIDD-UHFFFAOYSA-N^Y
(verify)

Nialamide (Niamid, Niamide, Nuredal, Surgex) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class that was used as an antidepressant.^[1] It was withdrawn by Pfizer several decades ago due to the risk of hepatotoxicity.^[2]^[3]

The antiatherogenic activity of nialamide was used to design pyridinolcarbamate.^[4]

References

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

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

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

Common
(non-specific)

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)

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

TPH	Inhibitors: AGN-2979 Fenclonine (PCPA) Telotristat

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

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