Isocarboxazid

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Isocarboxazid
Isocarboxazid structure.svg
Systematic (IUPAC) name
N′-benzyl-5-methylisoxazole-3-carbohydrazide
Clinical data
Trade names Marplan
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a605036
Pregnancy cat.
Legal status
Routes Oral
Pharmacokinetic data
Bioavailability ?
Metabolism Liver
Half-life ?
Excretion Urine
Identifiers
CAS number 59-63-2 YesY
ATC code N06AF01
PubChem CID 3759
DrugBank DB01247
ChemSpider 3628 YesY
UNII 34237V843T YesY
KEGG D02580 YesY
ChEMBL CHEMBL1201168 N
Chemical data
Formula C12H13N3O2 
Mol. mass 231.25
 N (what is this?)  (verify)

Isocarboxazid (Marplan, Marplon, Enerzer) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class used as an antidepressant.[1] 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,[2][3] though it is not as commonly employed in comparison to the others.[2][3]

Isocarboxazid is primarily used to treat mood and anxiety disorders. It has also been investigated in the treatment of Parkinson's disease and other dementia-related disorders. Although efficacious, isocarboxazid produces many side effects, which may include headaches, jaundice, chest pain, weight gain, orthostatic hypotension, fainting, dizziness, and tremors. Isocarboxazid, as well as other MAOIs, increase the levels of the monoamine neurotransmitters serotonin, dopamine, and norepinephrine in the brain.[4]

Classical MAOIs, including isocarboxazid, are used only very rarely in the present day due to prominent food and drug interactions and have been largely superseded by newer, safer, and more tolerable antidepressants such as the selective serotonin reuptake inhibitors (SSRIs). The cause of the interactions is due to the fact that 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.

See also[edit]

References[edit]

  1. ^ Fagervall I, Ross SB (April 1986). "Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors". Biochemical pharmacology 35 (8): 1381–7. doi:10.1016/0006-2952(86)90285-6. PMID 2870717. 
  2. ^ a b David Rosenberg (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. 
  3. ^ a b Lawrence A. Labbate; Maurizio Fava; Jerrold F. Rosenbaum; George W. Arana (28 March 2012). Handbook of Psychiatric Drug Therapy. Lippincott Williams & Wilkins. pp. 99–. ISBN 978-1-4511-5307-1. 
  4. ^ Volz, Hanz-Peter. (November 1998) “Monoamine Oxidase Inhibitors A Perspective on Their Use in The Elderly” Biochemical pharmacology (5) 341-352.