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); BR: Class C1 (Other controlled substances);
Identifiers
	IUPAC name N-benzyl-3-(N-(pyridine-4-carbonyl)hydrazino)propanamide;
CAS Number	51-12-7 ;
PubChem CID	4472;
DrugBank	DB04820 ;
ChemSpider	4317 ;
UNII	T2Q0RYM725;
KEGG	D07337 ;
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) ; Key:NOIIUHRQUVNIDD-UHFFFAOYSA-N ;
	(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irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class that was used as an antidepressant.^[2] It was withdrawn by Pfizer several decades ago due to the risk of hepatotoxicity.^[3]^[4]

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]

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ William Andrew Publishing (1 December 2006). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 2935–. ISBN 978-0-8155-1856-3.
^ Gad SC (26 April 2012). Safety Pharmacology in Pharmaceutical Development: Approval and Post Marketing Surveillance, Second Edition. CRC Press. pp. 138–. ISBN 978-1-4398-4567-7.
^ Shorter E (28 September 2008). Before Prozac: The Troubled History of Mood Disorders in Psychiatry: The Troubled History of Mood Disorders in Psychiatry. Oxford University Press. pp. 137–. ISBN 978-0-19-970933-5.
^ Council on Drugs (1971). AMA Drug Evaluations (Report). Chicago: American Medical Association. LCCN 75147249. Retrieved April 5, 2021.
^ Bencze WL, Hess R, DeStevens G (6 December 2012). "Hypolipidemic Agents". Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Vol. 13. Springer Science & Business Media. pp. 217–92. doi:10.1007/978-3-0348-7068-9_5. ISBN 9783642661907. PMID 4982663. Retrieved 3 October 2017. {{cite book}}: |journal= ignored (help)

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[Publishing2006-2] William Andrew Publishing (1 December 2006). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 2935–. ISBN 978-0-8155-1856-3.

[Gad2012-3] Gad SC (26 April 2012). Safety Pharmacology in Pharmaceutical Development: Approval and Post Marketing Surveillance, Second Edition. CRC Press. pp. 138–. ISBN 978-1-4398-4567-7.

[Shorter2008-4] Shorter E (28 September 2008). Before Prozac: The Troubled History of Mood Disorders in Psychiatry: The Troubled History of Mood Disorders in Psychiatry. Oxford University Press. pp. 137–. ISBN 978-0-19-970933-5.

[5] Council on Drugs (1971). AMA Drug Evaluations (Report). Chicago: American Medical Association. LCCN 75147249. Retrieved April 5, 2021.

[6] Bencze WL, Hess R, DeStevens G (6 December 2012). "Hypolipidemic Agents". Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Vol. 13. Springer Science & Business Media. pp. 217–92. doi:10.1007/978-3-0348-7068-9_5. ISBN 9783642661907. PMID 4982663. Retrieved 3 October 2017. {{cite book}}: |journal= ignored (help)

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See also

References