Isocarboxazid

Irreversible non-selective MAO inhibitor and antidepressant drug From Wikipedia, the free encyclopedia

Isocarboxazid, sold under the brand name Marplan among others, is a non-selective irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class used as an antidepressant.[5] 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,[6][7] though it is not as commonly employed in comparison to the others.[6][7]

Trade namesMarplan, Enerzer
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa605036
Routes of
administrationBy mouth
Quick facts Clinical data, Trade names ...
Isocarboxazid
Clinical data
Trade namesMarplan, Enerzer
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa605036
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityLow, peak at 1–2 h[2]
MetabolismLiver (Carboxylesterase[3])
MetabolitesHippuric acid[4]
Elimination half-life1.5–4 h[2]
ExcretionUrine
Identifiers
  • N′-benzyl-5-methylisoxazole-3-carbohydrazide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.399 Edit this at Wikidata
Chemical and physical data
FormulaC12H13N3O2
Molar mass231.255 g·mol−1
3D model (JSmol)
  • O=C(NNCc1ccccc1)c2noc(c2)C
  • 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)
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Isocarboxazid is primarily used to treat mood and anxiety disorders. It has also been investigated in the treatment of schizophrenia,[8] Parkinson's disease, and other dementia-related disorders.[9]

Isocarboxazid, as well as other MAOIs, increase the levels of the monoamine neurotransmitters serotonin, dopamine, norepinephrine, epinephrine, melatonin, and phenethylamine in the brain.[10]

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MAOIs, including isocarboxazid, are used only rarely due to prominent food and drug interactions and have been largely superseded by newer antidepressants such as the selective serotonin reuptake inhibitors (SSRIs).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.

Contraindications

Isocarboxazid is contraindicated[11][12] in certain patient populations, in combination with certain other drugs, and in combination with certain foods due to the risk of serious adverse reactions. Some notable contraindications include:

See also

References

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