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{{Short description|Antidepressant}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 416403788 | verifiedrevid = 416403788
| IUPAC_name = ''N''′-benzyl-5-methylisoxazole-3-carbohydrazide | IUPAC_name = ''N''′-benzyl-5-methylisoxazole-3-carbohydrazide
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| pregnancy_category = C (]) | pregnancy_category = C (])
| legal_AU = S4 | legal_AU = S4
| legal_BR = C1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_NZ = <!-- Class A, B, C -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_EU =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_status = Rx-only | legal_status = Rx-only
| routes_of_administration = Oral | routes_of_administration = Oral
<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = Low, peak at 1&ndash;2&nbsp;h<ref name=isocoverview>{{cite book | vauthors = Owens DC, Johnstone EC, Lawrie SM | chapter = Clinical psychopharmacology. | title = Companion to psychiatric studies. | date = January 2010 | pages = 227–294 | doi = 10.1016/B978-0-7020-3137-3.00011-5 | isbn = 9780702031373 }}</ref>
| bioavailability = ?
| metabolism = ] (]<ref>{{cite journal | vauthors = Moroi K, Kuga T | title = Inhibitory effect of leptophos on carboxylesterase (isocarboxazid amidase) in rat liver | journal = Toxicology Letters | volume = 11 | issue = 1–2 | pages = 81–85 | date = April 1982 | pmid = 6178187 | doi = 10.1016/0378-4274(82)90110-2 }}</ref>)
| metabolism = ]
| elimination_half-life = ? | elimination_half-life = 1.5&ndash;4&nbsp;h<ref name=isocoverview/>
| excretion = ] | excretion = ]
| metabolites = ]<ref>{{cite web|url=https://go.drugbank.com/reactions/2399|website=go.drugbank.com|access-date=27 October 2021|title=Reaction: Isocarboxazid to 1 product}}</ref>
<!--Identifiers--> <!--Identifiers-->
| IUPHAR_ligand = 7204 | IUPHAR_ligand = 7204
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<!--Chemical data--> <!--Chemical data-->
| C=12 | H=13 | N=3 | O=2 | C=12 | H=13 | N=3 | O=2
| molecular_weight = 231.25 g/mol
| smiles = O=C(NNCc1ccccc1)c2noc(c2)C | smiles = O=C(NNCc1ccccc1)c2noc(c2)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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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 = Biochemical Pharmacology | volume = 35 | issue = 8 | pages = 1381–1387 | date = April 1986 | pmid = 2870717 | doi = 10.1016/0006-2952(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| vauthors = Rosenberg D |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| vauthors = Labbate LA, Fava M, Rosenbaum JF, Arana GW |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. Although efficacious, isocarboxazid produces many ]s, which may include ]s, ], ], ], ], ], ], and ]s. 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 ],<ref>{{cite journal | vauthors = Darling HF | title = Isocarboxazid (marplan) in ambulatory psychiatric patients | journal = The American Journal of Psychiatry | volume = 116 | issue = 4 | pages = 355–356 | date = October 1959 | pmid = 13814129 | doi = 10.1176/ajp.116.4.355 }}</ref> ] and other ]-related disorders.<ref>{{cite journal | vauthors = Riederer P, Laux G | title = MAO-inhibitors in Parkinson's Disease | journal = Experimental Neurobiology | volume = 20 | issue = 1 | pages = 1–17 | date = March 2011 | pmid = 22110357 | pmc = 3213739 | doi = 10.5607/en.2011.20.1.1 | publisher = Experimental Neurology }}</ref>

Isocarboxazid, as well as other MAOIs, increase the levels of the ] ], ], ], ], ], ] in the brain.<ref name="pmid9829163">{{cite journal | vauthors = Volz HP, Gleiter CH | title = Monoamine oxidase inhibitors. A perspective on their use in the elderly | journal = Drugs & Aging | volume = 13 | issue = 5 | pages = 341–55 | date = November 1998 | pmid = 9829163 | doi = 10.2165/00002512-199813050-00002 | s2cid = 71158339 }}</ref>
Classical MAOIs, including isocarboxazid, are used only very rarely in the present day due to prominent ] and ]s and have been largely superseded by newer, safer, and more tolerable 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 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 ].


== See also == == See also ==
Line 58: Line 71:


{{Antidepressants}} {{Antidepressants}}
{{Monoamine metabolism modulators}}
{{Adrenergics}}
{{Hydrazines}} {{Hydrazines}}


] ]
] ]
]
] ]

Latest revision as of 18:46, 23 August 2024

Antidepressant 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)
  • BR: Class C1 (Other controlled substances)
  • US: WARNING
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityLow, peak at 1–2 h
MetabolismLiver (Carboxylesterase)
MetabolitesHippuric acid
Elimination half-life1.5–4 h
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 mass231.255 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 schizophrenia, Parkinson's disease and other dementia-related disorders.

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

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.

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. 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. ^ 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. ^ 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. ^ 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.
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: