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irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class that was used as an antidepressant.[1] It was withdrawn by Pfizer several decades ago due to the risk of hepatotoxicity.[2][3]

Nialamide
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
Identifiers
IUPAC name
  • N-benzyl-3-(N-(pyridine-4-carbonyl)hydrazino)propanamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.073
Chemical and physical data
FormulaC16H18N4O2
Molar mass298.346 g·mol−1
3D model (JSmol)
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)

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.[4]

The antiatherogenic activity of nialamide was used to design pyridinolcarbamate.[5]

See also

References
  1. William Andrew Publishing (1 December 2006). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 2935–. ISBN 978-0-8155-1856-3.
  2. 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.
  3. 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.
  4. Council on Drugs (1971). AMA Drug Evaluations (Report). Chicago: American Medical Association. LCCN 75147249. Retrieved April 5, 2021.
  5. Bencze WL, Hess R, DeStevens G (6 December 2012). "Hypolipidemic agents". Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progrès des Recherches Pharmaceutiques. Springer Science & Business Media. 13: 217–92. doi:10.1007/978-3-0348-7068-9_5. ISBN 9783642661907. PMID 4982663. Retrieved 3 October 2017.
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