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Isocarboxazid information


Isocarboxazid
Clinical data
Trade namesMarplan
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa605036
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)[2]
  • US: WARNING[1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityLow, peak at 1-2 h[3]
MetabolismLiver (Carboxylesterase[5])
MetabolitesHippuric acid[4]
Elimination half-life1.5-4h[3]
ExcretionUrine
Identifiers
IUPAC name
  • N′-benzyl-5-methylisoxazole-3-carbohydrazide
CAS Number
  • 59-63-2 checkY
PubChem CID
  • 3759
IUPHAR/BPS
  • 7204
DrugBank
  • DB01247 checkY
ChemSpider
  • 3628 checkY
UNII
  • 34237V843T
KEGG
  • D02580 checkY
ChEMBL
  • ChEMBL1201168 ☒N
CompTox Dashboard (EPA)
  • DTXSID4023171 Edit this at Wikidata
ECHA InfoCard100.000.399 Edit this at Wikidata
Chemical and physical data
FormulaC12H13N3O2
Molar mass231.255 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) checkY
  • Key:XKFPYPQQHFEXRZ-UHFFFAOYSA-N checkY
 ☒NcheckY (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.[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MAOIs, including isocarboxazid, are used only rarely due to prominent food and drug interactions and have been largely superseded by newer antidepressants such as the selective serotonin reuptake inhibitors (SSRIs).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.

  1. ^ "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.
  2. ^ 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.
  3. ^ 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.
  4. ^ "Reaction: Isocarboxazid to 1 product". go.drugbank.com. Retrieved 27 October 2021.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ 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.

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Isocarboxazid

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Phenelzine

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as an antidepressant and anxiolytic. Along with tranylcypromine and isocarboxazid, phenelzine is one of the few non-selective and irreversible MAOIs still...

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Pharmahuasca

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has been recorded and is safer than older irreversible MAOIs (such as isocarboxazid) due to its significantly shorter and more selective effects (although...

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Monoamine oxidase inhibitor

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2006. Nonselective MAO-A/MAO-B inhibitors Hydrazine (antidepressant) Isocarboxazid (Marplan) Hydracarbazine Phenelzine (Nardil, Nardelzine) Non-hydrazines...

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List of antidepressants

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as noradrenergic and specific serotonergic antidepressants (NaSSAs). Isocarboxazid (Marplan) Phenelzine (Nardil) Tranylcypromine (Parnate) Discontinued/withdrawn...

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Dibenzoylhydrazine

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benzoic acid amine, and is related to benzoyl peroxide, tricarban, isocarboxazid, and hydrazine. The substance was patented as an "ecdysone receptor...

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Nefopam

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monoamine oxidase inhibitors such as phenelzine, tranylcypromine or isocarboxazid within the past 30 days and those with myocardial infarction pain, mostly...

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Ketamine

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Dexbrompheniramine

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and runny nose. MAO inhibitors within 14 days. MAO inhibitors include isocarboxazid, linezolid, phenelzine, rasagiline, selegiline, and tranylcypromine...

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Psychiatric medication

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(Effexor), SNRI Bupropion (Wellbutrin), NDRI Mirtazapine (Remeron), NaSSA Isocarboxazid (Marplan), MAOI Phenelzine (Nardil), MAOI Tranylcypromine (Parnate)...

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ATC code N06

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N06AB08 Fluvoxamine N06AB09 Etoperidone N06AB10 Escitalopram N06AF01 Isocarboxazid N06AF02 Nialamide N06AF03 Phenelzine N06AF04 Tranylcypromine N06AF05...

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Brazilian Controlled Drugs and Substances Act

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Hydroxydione Homofenazine Imiclopazine Imipramine Imipraminoxide Iproclozide Isocarboxazid Isoflurane Cenestil (Isopropyl-crotonyl-urea) (CAS: 60364-26-3 , CID...

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Myristicin

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interactions. Those taking antidepressants that are MAOIs (such as phenelzine, isocarboxazid, tranylcypromine or selegiline) or taking selective serotonin re-uptake...

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Drug of last resort

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Therapeutics. 51 (10): 763–70. doi:10.5414/CP201898. PMID 23993253. "Marplan (isocarboxazid) Tablets. Full Prescribing Information" (PDF). Validus Pharmaceuticals...

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Pethidine

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be dangerous with monoamine oxidase inhibitors (e.g., furazolidone, isocarboxazid, moclobemide, phenelzine, procarbazine, selegiline, tranylcypromine)...

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Dopaminergic

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including nonselective agents such as phenelzine, tranylcypromine, and isocarboxazid, MAOA selective agents like moclobemide, and MAOB selective agents such...

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Bupropion

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Non-selective Irreversible: Benmoxin‡ Iproclozide‡ Iproniazid‡ Isocarboxazid Isoniazid# Linezolid# Mebanazine‡ Nialamide‡ Octamoxin‡ Phenelzine Pheniprazine‡...

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Vortioxetine

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Selective serotonin reuptake inhibitor

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Non-selective Irreversible: Benmoxin‡ Iproclozide‡ Iproniazid‡ Isocarboxazid Isoniazid# Linezolid# Mebanazine‡ Nialamide‡ Octamoxin‡ Phenelzine Pheniprazine‡...

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Methylene blue

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Antidepressant

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Buspirone

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Anxiolytic

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Venlafaxine

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Escitalopram

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Trazodone

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