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Isocarboxazid
Clinical data
Trade names	Marplan
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a605036
Pregnancy; category	C (USA);
Routes of; administration	Oral
ATC code	N06AF01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); US: WARNING; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Low, peak at 1–2 h
Metabolism	Liver (Carboxylesterase)
Metabolites	Hippuric acid
Elimination half-life	1.5–4 h
Excretion	Urine
Identifiers
	IUPAC name N′-benzyl-5-methylisoxazole-3-carbohydrazide;
CAS Number	59-63-2 ;
PubChem CID	3759;
IUPHAR/BPS	7204;
DrugBank	DB01247 ;
ChemSpider	3628 ;
UNII	34237V843T;
KEGG	D02580 ;
ChEMBL	ChEMBL1201168 ;
CompTox Dashboard (EPA)	DTXSID4023171 ;
ECHA InfoCard	100.000.399
Chemical and physical data
Formula	C12H13N3O2
Molar mass	231.255 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(NNCc1ccccc1)c2noc(c2)C;
	InChI InChI=1S/C12H13N3O2/c1-9-7-11(15-17-9)12(16)14-13-8-10-5-3-2-4-6-10/h2-7,13H,8H2,1H3,(H,14,16) ; Key:XKFPYPQQHFEXRZ-UHFFFAOYSA-N ;
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Isocarboxazid (Marplan, Marplon, Enerzer) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class used as an antidepressant.^[6] Along with phenelzine and tranylcypromine, it is one of only three classical MAOIs still available for clinical use in the treatment of psychiatric disorders in the United States,^[7]^[8] though it is not as commonly employed in comparison to the others.^[7]^[8]

Isocarboxazid is primarily used to treat mood and anxiety disorders. It has also been investigated in the treatment of schizophrenia,^[9] Parkinson's disease and other dementia-related disorders.^[10]

Isocarboxazid, as well as other MAOIs, increase the levels of the monoamine neurotransmitters serotonin, dopamine, norepinephrine, epinephrine, melatonin, phenethylamine in the brain.^[11]

Classical MAOIs, including isocarboxazid, are used only rarely due to prominent food and drug interactions and have been largely superseded by newer antidepressants such as the selective serotonin reuptake inhibitors (SSRIs). The cause of the interactions is because MAOIs inhibit the metabolism of dietary amines (e.g., tyramine) and the monoamine neurotransmitters. In combination with other drugs that increase the levels of the monoamine neurotransmitters such as the SSRIs, or with certain foods high in dietary amines such as aged cheeses, MAOIs can produce dangerous elevations of monoamine neurotransmitters resulting in potentially life-threatening syndromes such as hypertensive crisis and serotonin syndrome.

References

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ 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.
^ ^a ^b Owens DC, Johnstone EC, Lawrie SM (January 2010). "Clinical psychopharmacology.". Companion to psychiatric studies. pp. 227–294. doi:10.1016/B978-0-7020-3137-3.00011-5. ISBN 9780702031373.
^ "Reaction: Isocarboxazid to 1 product". go.drugbank.com. Retrieved 27 October 2021.
^ Moroi K, Kuga T (April 1982). "Inhibitory effect of leptophos on carboxylesterase (isocarboxazid amidase) in rat liver". Toxicology Letters. 11 (1–2): 81–85. doi:10.1016/0378-4274(82)90110-2. PMID 6178187.
^ Fagervall I, Ross SB (April 1986). "Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors". Biochemical Pharmacology. 35 (8): 1381–1387. doi:10.1016/0006-2952(86)90285-6. PMID 2870717.
^ ^a ^b Rosenberg D (21 August 2013). Pocket Guide For The Textbook Of Pharmacotherapy For Child And Adolescent Psychiatric Disorders. Routledge. pp. 176–. ISBN 978-1-134-86002-9.
^ ^a ^b Labbate LA, Fava M, Rosenbaum JF, Arana GW (28 March 2012). Handbook of Psychiatric Drug Therapy. Lippincott Williams & Wilkins. pp. 99–. ISBN 978-1-4511-5307-1.
^ Darling HF (October 1959). "Isocarboxazid (marplan) in ambulatory psychiatric patients". The American Journal of Psychiatry. 116 (4): 355–356. doi:10.1176/ajp.116.4.355. PMID 13814129.
^ Riederer P, Laux G (March 2011). "MAO-inhibitors in Parkinson's Disease". Experimental Neurobiology. 20 (1). Experimental Neurology: 1–17. doi:10.5607/en.2011.20.1.1. PMC 3213739. PMID 22110357.
^ Volz HP, Gleiter CH (November 1998). "Monoamine oxidase inhibitors. A perspective on their use in the elderly". Drugs & Aging. 13 (5): 341–55. doi:10.2165/00002512-199813050-00002. PMID 9829163. S2CID 71158339.