Nialamide

Nialamide (Niamid, Niamide, Nuredal, Surgex) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class that was used as an antidepressant.^[2] It was withdrawn by Pfizer several decades ago due to the risk of hepatotoxicity.^[3][4]

AHFS/Drugs.comInternational Drug Names

Routes of
administrationOral

ATC code

• N06AF02 (WHO)

Legal status

• AU: S4 (Prescription only)
• BR: Class C1 (Other controlled substances)^[1]

Quick facts Clinical data, AHFS/Drugs.com ...

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) BR: Class C1 (Other controlled substances)[1]
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
KEGG	D07337 Y
ChEBI	CHEBI:94510
ChEMBL	ChEMBL1256841
CompTox Dashboard (EPA)	DTXSID1023362
ECHA InfoCard	100.000.073
Chemical and physical data
Formula	C16H18N4O2
Molar mass	298.346 g·mol−1
3D model (JSmol)	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)

Close

Side effects include agitation and insomnia, less frequently dry mouth, dizziness, blurred vision, and hypomania, and rarely leukopenia and hepatitis. As with other MAOIs, a hypertensive crisis can be triggered by co-ingestion of tyramine. It is metabolized into isoniazid, an anti-tuberculosis agent, and so is contraindicated in patients with tuberculosis. The recommended dosage range is 75 to 200 mg per day, with maintenance doses as low as 12.5 mg every other day.^[5]

The antiatherogenic activity of nialamide was used to design pyridinolcarbamate.^[6]