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'''Isocarboxazid''' ('''Marplan''', '''Marplon''', '''Enerzer''') is a non-selective, ] ] (MAOI) of the ] class used as an ].<ref name="pmid2870717">{{cite journal |vauthors=Fagervall I, Ross SB |title=Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors |journal=] |volume=35 |issue=8 |pages=1381–7 |date=April 1986 |pmid=2870717 |doi= 10.1016/0006-2952(86)90285-6|url=http://linkinghub.elsevier.com/retrieve/pii/0006-2952(86)90285-6}}</ref> Along with ] and ], it is one of only three classical MAOIs still available for clinical use in the treatment of psychiatric disorders in the ],<ref name="Rosenberg2013">{{cite book|author=David Rosenberg|title=Pocket Guide For The Textbook Of Pharmacotherapy For Child And Adolescent Psychiatric Disorders|url=https://books.google.com/books?id=fep_AAAAQBAJ&pg=PA176|date=21 August 2013|publisher=Routledge|isbn=978-1-134-86002-9|pages=176–}}</ref><ref name="LabbateFava2012">{{cite book|author1=Lawrence A. Labbate|author2=Maurizio Fava|author3=Jerrold F. Rosenbaum|author4=George W. Arana|title=Handbook of Psychiatric Drug Therapy|url=https://books.google.com/books?id=xrZfcE8MydIC&pg=PA99|date=28 March 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-5307-1|pages=99–}}</ref> though it is not as commonly employed in comparison to the others.<ref name="Rosenberg2013" /><ref name="LabbateFava2012" /> '''Isocarboxazid''' ('''Marplan''', '''Marplon''', '''Enerzer''') is a non-selective, ] ] (MAOI) of the ] class used as an ].<ref name="pmid2870717">{{cite journal |vauthors=Fagervall I, Ross SB |title=Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors |journal=] |volume=35 |issue=8 |pages=1381–7 |date=April 1986 |pmid=2870717 |doi= 10.1016/0006-2952(86)90285-6|url=http://linkinghub.elsevier.com/retrieve/pii/0006-2952(86)90285-6}}</ref> Along with ] and ], it is one of only three classical MAOIs still available for clinical use in the treatment of psychiatric disorders in the ],<ref name="Rosenberg2013">{{cite book|author=David Rosenberg|title=Pocket Guide For The Textbook Of Pharmacotherapy For Child And Adolescent Psychiatric Disorders|url=https://books.google.com/books?id=fep_AAAAQBAJ&pg=PA176|date=21 August 2013|publisher=Routledge|isbn=978-1-134-86002-9|pages=176–}}</ref><ref name="LabbateFava2012">{{cite book|author1=Lawrence A. Labbate|author2=Maurizio Fava|author3=Jerrold F. Rosenbaum|author4=George W. Arana|title=Handbook of Psychiatric Drug Therapy|url=https://books.google.com/books?id=xrZfcE8MydIC&pg=PA99|date=28 March 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-5307-1|pages=99–}}</ref> though it is not as commonly employed in comparison to the others.<ref name="Rosenberg2013" /><ref name="LabbateFava2012" />


Isocarboxazid is primarily used to treat ] and ]s. It has also been investigated in the treatment of ] and other ]-related disorders. Isocarboxazid may produce ]s, ], ], and minor anticholinergic ] <ref>{{cite journal |vauthors=Larsen JK, Krogh-Nielsen L, Brøsen K |title=The Monoamine Oxidase Inhibitor Isocarboxazid is a Relevant Treatment Option in Treatment-Resistant Depression |journal=Health Care: Current Reviews |volume=4|issue=2 |date=April 2016 | url=https://core.ac.uk/download/pdf/50716122.pdf}}</ref>Isocarboxazid, as well as other MAOIs, increase the levels of the ] ] ], ], and ] in the brain.<ref>Volz, Hanz-Peter. (November 1998) “Monoamine Oxidase Inhibitors A Perspective on Their Use in The Elderly” Biochemical pharmacology (5) 341-352.</ref> Isocarboxazid is primarily used to treat ] and ]s. It has also been investigated in the treatment of ] and other ]-related disorders. Isocarboxazid may produce ]s, ], ], and minor anticholinergic ].<ref>{{cite journal |vauthors=Larsen JK, Krogh-Nielsen L, Brøsen K |title=The Monoamine Oxidase Inhibitor Isocarboxazid is a Relevant Treatment Option in Treatment-Resistant Depression |journal=Health Care: Current Reviews |volume=4|issue=2 |date=April 2016 | url=https://core.ac.uk/download/pdf/50716122.pdf}}</ref> Isocarboxazid, as well as other MAOIs, increase the levels of the ] ] ], ], and ] in the brain.<ref>Volz, Hanz-Peter. (November 1998) “Monoamine Oxidase Inhibitors A Perspective on Their Use in The Elderly” Biochemical pharmacology (5) 341-352.</ref>
Classical MAOIs, including isocarboxazid, are used only very rarely due to prominent ] and ]s and have been largely superseded by newer antidepressants such as the ]s (SSRIs). The cause of the interactions is because MAOIs inhibit the ] of dietary amines (e.g., ]) 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 ]s, MAOIs can produce dangerous elevations of monoamine neurotransmitters resulting in potentially life-threatening syndromes such as ] and ]. Classical MAOIs, including isocarboxazid, are used only very rarely due to prominent ] and ]s and have been largely superseded by newer antidepressants such as the ]s (SSRIs). The cause of the interactions is because MAOIs inhibit the ] of dietary amines (e.g., ]) 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 ]s, MAOIs can produce dangerous elevations of monoamine neurotransmitters resulting in potentially life-threatening syndromes such as ] and ].

Revision as of 20:53, 10 August 2018

Pharmaceutical compound
Isocarboxazid
Clinical data
Trade namesMarplan
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa605036
Pregnancy
category
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: WARNING
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability?
MetabolismLiver
Elimination half-life?
ExcretionUrine
Identifiers
IUPAC name
  • 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 mass231.25 g/mol g·mol
3D model (JSmol)
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
  (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. 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, though it is not as commonly employed in comparison to the others.

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. Isocarboxazid may produce headaches, orthostatic hypotension, dizziness, and minor anticholinergic side effects. Isocarboxazid, as well as other MAOIs, increase the levels of the monoamine neurotransmitters serotonin, dopamine, and norepinephrine in the brain.

Classical MAOIs, including isocarboxazid, are used only very 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.

See also

References

  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. 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.
  3. ^ 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.
  4. ^ 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.
  5. Larsen JK, Krogh-Nielsen L, Brøsen K (April 2016). "The Monoamine Oxidase Inhibitor Isocarboxazid is a Relevant Treatment Option in Treatment-Resistant Depression" (PDF). Health Care: Current Reviews. 4 (2).
  6. Volz, Hanz-Peter. (November 1998) “Monoamine Oxidase Inhibitors A Perspective on Their Use in The Elderly” Biochemical pharmacology (5) 341-352.
Antidepressants (N06A)
Specific reuptake inhibitors and/or receptor modulators
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
Tricyclic and tetracyclic antidepressants
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Monoamine oxidase inhibitors
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Adjunctive therapies
Miscellaneous
Monoamine metabolism modulators
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
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins
Hydrazines
Categories: