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Isocarboxazid

From Wikipedia, the free encyclopedia
Irreversible non-selective Monoamine Oxidase Inhibitor Antidepressant
Pharmaceutical compound
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[4])
MetabolitesHippuric acid[3]
Eliminationhalf-life1.5–4 h[2]
ExcretionUrine
Identifiers
  • N′-benzyl-5-methylisoxazole-3-carbohydrazide
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.000.399Edit 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)

Isocarboxazid, sold under the brand nameMarplan among others, is a non-selectiveirreversiblemonoamine oxidase inhibitor (MAOI) of thehydrazine class used as anantidepressant.[5] Along withphenelzine andtranylcypromine, it is one of only three classical MAOIs still available for clinical use in the treatment ofpsychiatric disorders in the United States,[6][7] though it is not as commonly employed in comparison to the others.[6][7]

Isocarboxazid is primarily used to treatmood andanxiety disorders. It has also been investigated in the treatment ofschizophrenia,[8]Parkinson's disease, and otherdementia-related disorders.[9]

Isocarboxazid, as well as other MAOIs, increase the levels of themonoamine neurotransmittersserotonin,dopamine,norepinephrine,epinephrine,melatonin, andphenethylamine in the brain.[10]

Classical MAOIs, including isocarboxazid, are used only rarely due to prominentfood anddrug interactions and have been largely superseded by newer antidepressants such as theselective serotonin reuptake inhibitors (SSRIs). The cause of the interactions is because MAOIs inhibit themetabolism 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 asaged cheeses, MAOIs can produce dangerous elevations of monoamine neurotransmitters resulting in potentially life-threatening syndromes such ashypertensive crisis andserotonin syndrome.

Contraindications

[edit]

Isocarboxazid iscontraindicated[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

[edit]

References

[edit]
  1. ^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. Retrieved2023-08-16.
  2. ^abOwens 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.
  3. ^"Reaction: Isocarboxazid to 1 product".go.drugbank.com. Retrieved27 October 2021.
  4. ^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.
  5. ^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.
  6. ^abRosenberg 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.
  7. ^abLabbate 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.
  8. ^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.
  9. ^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.
  10. ^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.
  11. ^"Marplan Drug Label".dailymed.nlm.nih.gov. Retrieved2025-01-25.
  12. ^"Marplan® (isocarboxazid) | Safety Information".marplan.com. Retrieved2025-01-25.
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Miscellaneous
Non-specific
AAADTooltip Aromatic L-amino acid decarboxylase
MAOTooltip Monoamine oxidase
Phenethylamines
(dopamine,epinephrine,
norepinephrine)
PAHTooltip Phenylalanine hydroxylase
THTooltip Tyrosine hydroxylase
DBHTooltip Dopamine beta-hydroxylase
PNMTTooltip Phenylethanolamine N-methyltransferase
COMTTooltip Catechol-O-methyl transferase
Tryptamines
(serotonin,melatonin)
TPHTooltip Tryptophan hydroxylase
AANATTooltip Serotonin N-acetyl transferase
ASMTTooltip Acetylserotonin O-methyltransferase
Histamine
HDCTooltip Histidine decarboxylase
HNMTTooltip Histamine N-methyltransferase
DAOTooltip Diamine oxidase
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