<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3075</id>
  <title>T3D3033</title>
  <common-name>Isocarboxazid</common-name>
  <description>Isocarboxazid is only found in individuals that have used or taken this drug. It is an MAO inhibitor that is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in the treatment of panic disorder and the phobic disorders. (From AMA, Drug Evaluations Annual, 1994, p311). Isocarboxazid works by irreversibly blocking the action of a chemical substance known as monoamine oxidase (MAO) in the nervous system. MAO subtypes A and B are involved in the metabolism of serotonin and catecholamine neurotransmitters such as epinephrine, norepinephrine, and dopamine. Isocarboxazid, as a nonselective MAO inhibitor, binds irreversibly to monoamine oxidase&amp;ndash;A (MAO-A) and monoamine oxidase&amp;ndash;B (MAO-B). The reduced MAO activity results in an increased concentration of these neurotransmitters in storage sites throughout the central nervous system (CNS) and sympathetic nervous system. This increased availability of one or more monoamines is the basis for the antidepressant activity of MAO inhibitors.</description>
  <cas>59-63-2</cas>
  <pubchem-id>3759</pubchem-id>
  <chemical-formula>C12H13N3O2</chemical-formula>
  <weight>231.100780</weight>
  <appearance>White powder.</appearance>
  <melting-point>105-106°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1.6 mg/mL at 25°C</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Well absorbed from the gastrointestinal tract.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Isocarboxazid works by irreversibly blocking the action of a chemical substance known as monoamine oxidase (MAO) in the nervous system. MAO subtypes A and B are involved in the metabolism of serotonin and catecholamine neurotransmitters such as epinephrine, norepinephrine, and dopamine. Isocarboxazid, as a nonselective MAO inhibitor, binds irreversibly to monoamine oxidase&amp;ndash;A (MAO-A) and monoamine oxidase&amp;ndash;B (MAO-B). The reduced MAO activity results in an increased concentration of these neurotransmitters in storage sites throughout the central nervous system (CNS) and sympathetic nervous system. This increased availability of one or more monoamines is the basis for the antidepressant activity of MAO inhibitors.</mechanism-of-toxicity>
  <metabolism>Hepatic and rapid (by oxidation).</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>May be used to treat major depressive disorder.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Signs of overdose include severe anxiety, confusion, convulsions, cool clammy skin, severe dizziness, severe drowsiness, fast and irregular pulse, fever, hallucinations, severe headache, high or low blood pressure, hyperactive reflexes, muscle stiffness, respiratory depression or failure, slowed reflexes, sweating, severe trouble in sleeping, and unusual irritability.</symptoms>
  <treatment>General supportive measures should be used, along with immediate gastric lavage or emetics. If the latter are given, the danger of aspiration must be borne in mind. An adequate airway should be maintained, with supplemental oxygen if necessary. The mechanism by which amine-oxidase inhibitors produce hypotension is not fully understood, but there is evidence that these agents block the vascular bed response. Thus it is suggested that plasma may be of value in the management of this hypotension. Administration of pressor amines such as levarterenol bitartrate may be of limited value (note that their effects may be potentiated by Isocarboxazid). Continue treatment for several days until homeostasis is restored. Liver function studies are recommended during the 4 to 6 weeks after recovery, as well as the time of overdosage.</treatment>
  <created-at type="dateTime">2009-07-21T20:28:44Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:59:06Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Isocarboxazid</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>775119</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Isocarboxazid</stitch-id>
  <drugbank-id>DB01247</drugbank-id>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC1=CC(=NO1)C(=O)NNCC1=CC=CC=C1</moldb-smiles>
  <moldb-formula>C12H13N3O2</moldb-formula>
  <moldb-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)</moldb-inchi>
  <moldb-inchikey>XKFPYPQQHFEXRZ-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">231.2505</moldb-average-mass>
  <moldb-mono-mass type="decimal">231.100776675</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.49</logp>
  <hmdb-id>HMDB15377</hmdb-id>
  <chembl-id>CHEMBL1201168</chembl-id>
  <chemspider-id>3628</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;U.S. Patent 2,908,688.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002387</chemdb-id>
  <dsstox-id>DTXSID4023171</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00007049</susdat-id>
  <iupac>N'-benzyl-5-methyl-1,2-oxazole-3-carbohydrazide</iupac>
  <moldb-polar-surface-area>67.16</moldb-polar-surface-area>
  <moldb-refractivity>74.78030000000001</moldb-refractivity>
  <moldb-polarizability>24.510960717633893</moldb-polarizability>
  <moldb-rotatable-bond-count>4</moldb-rotatable-bond-count>
  <moldb-acceptor-count>3</moldb-acceptor-count>
  <moldb-donor-count>2</moldb-donor-count>
  <moldb-pka-strongest-acidic>12.021473156034329</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>3.123385867616713</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>1.19</moldb-alogps-logp>
  <moldb-alogps-logs>-3.01</moldb-alogps-logs>
  <moldb-alogps-solubility>2.24e-01 g/l</moldb-alogps-solubility>
</compound>
