nialamide

{{Short description|Antidepressant}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| verifiedrevid = 447387851

| IUPAC_name = N-benzyl-3-(N-(pyridine-4-carbonyl)hydrazino)propanamide

| image =Nialamide.svg

| image_class = skin-invert-image

| tradename =

| Drugs.com = {{drugs.com|international|nialamide}}

| pregnancy_category =

| legal_AU = S4

| legal_BR = C1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

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| legal_DE =

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| legal_US =

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| routes_of_administration = Oral

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 51-12-7

| ATC_prefix = N06

| ATC_suffix = AF02

| PubChem = 4472

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB04820

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4317

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = T2Q0RYM725

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07337

| ChEBI = 94510

| ChEMBL = 1256841

| C=16 | H=18 | N=4 | O=2

| smiles = O=C(NNCCC(=O)NCc1ccccc1)c2ccncc2

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NOIIUHRQUVNIDD-UHFFFAOYSA-N

}}

Nialamide (Niamid, Niamide, Nuredal, Surgex) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class that was used as an antidepressant.{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia | edition = 3rd | url = https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA2935|date=1 December 2006|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=2935–}} It was withdrawn by Pfizer several decades ago due to the risk of hepatotoxicity.{{cite book| vauthors = Gad SC |title=Safety Pharmacology in Pharmaceutical Development: Approval and Post Marketing Surveillance, Second Edition|url=https://books.google.com/books?id=AHA2g-qq6WwC&pg=PA138|date=26 April 2012|publisher=CRC Press|isbn=978-1-4398-4567-7|pages=138–}}{{cite book| first = Edward | last = Shorter |title=Before Prozac: The Troubled History of Mood Disorders in Psychiatry: The Troubled History of Mood Disorders in Psychiatry|url=https://books.google.com/books?id=8VaYF8pIPxgC&pg=PA137|date=28 September 2008|publisher=Oxford University Press|isbn=978-0-19-970933-5|pages=137–}}

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.{{cite report |publisher=American Medical Association |location=Chicago |title=AMA Drug Evaluations |date=1971 |author=Council on Drugs |lccn=75147249 |url=https://archive.org/details/amadrugevaluatio00coun |access-date=April 5, 2021}}

The antiatherogenic activity of nialamide was used to design pyridinolcarbamate.{{cite book | vauthors = Bencze WL, Hess R, DeStevens G | chapter = Hypolipidemic Agents | title = Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques | series = Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progres des Recherches Pharmaceutiques | volume = 13 | pages = 217–92 | date = 6 December 2012 | pmid = 4982663 | doi = 10.1007/978-3-0348-7068-9_5 | chapter-url = https://books.google.com/books?id=a1bmCAAAQBAJ&pg=PA387 | access-date = 3 October 2017 | publisher = Springer Science & Business Media | isbn = 9783642661907 }}