<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3062</id>
  <title>T3D3020</title>
  <common-name>Mitoxantrone</common-name>
  <description>Mitoxantrone is only found in individuals that have used or taken this drug. It is an anthracenedione-derived antineoplastic agent. Mitoxantrone, a DNA-reactive agent that intercalates into deoxyribonucleic acid (DNA) through hydrogen bonding, causes crosslinks and strand breaks. Mitoxantrone also interferes with ribonucleic acid (RNA) and is a potent inhibitor of topoisomerase II, an enzyme responsible for uncoiling and repairing damaged DNA. It has a cytocidal effect on both proliferating and nonproliferating cultured human cells, suggesting lack of cell cycle phase specificity.</description>
  <cas>65271-80-9</cas>
  <pubchem-id>4212</pubchem-id>
  <chemical-formula>C22H28N4O6</chemical-formula>
  <weight>444.200890</weight>
  <appearance nil="true"/>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>7.34e-01 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Intravenous injection. Poorly absorbed following oral administration.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Mitoxantrone, a DNA-reactive agent that intercalates into deoxyribonucleic acid (DNA) through hydrogen bonding, causes crosslinks and strand breaks. Mitoxantrone also interferes with ribonucleic acid (RNA) and is a potent inhibitor of topoisomerase II, an enzyme responsible for uncoiling and repairing damaged DNA. It has a cytocidal effect on both proliferating and nonproliferating cultured human cells, suggesting lack of cell cycle phase specificity.</mechanism-of-toxicity>
  <metabolism>HepaticHalf Life: 75 hours</metabolism>
  <toxicity></toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>2B, possibly carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>For the treatment of secondary (chronic) progressive, progressive relapsing, or worsening relapsing-remitting multiple sclerosis. Mitoxantrone is an Anthracenedione (not an anthracycline) antineoplastic agent.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Cardiomyopathy is a particularly concerning effect as it is irreversible. [Wikipedia]</health-effects>
  <symptoms>Severe leukopenia with infection.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:28:38Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:58:43Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Mitoxantrone</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C11195</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>50729</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Mitoxantrone</stitch-id>
  <drugbank-id>DB01204</drugbank-id>
  <pdb-id>MIX</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>OCCNCCNC1=C2C(=O)C3=C(O)C=CC(O)=C3C(=O)C2=C(NCCNCCO)C=C1</moldb-smiles>
  <moldb-formula>C22H28N4O6</moldb-formula>
  <moldb-inchi>InChI=1S/C22H28N4O6/c27-11-9-23-5-7-25-13-1-2-14(26-8-6-24-10-12-28)18-17(13)21(31)19-15(29)3-4-16(30)20(19)22(18)32/h1-4,23-30H,5-12H2</moldb-inchi>
  <moldb-inchikey>KKZJGLLVHKMTCM-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">444.4809</moldb-average-mass>
  <moldb-mono-mass type="decimal">444.200884648</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Liquid</state>
  <logp>-3.1</logp>
  <hmdb-id>HMDB15335</hmdb-id>
  <chembl-id>CHEMBL58</chembl-id>
  <chemspider-id>4067</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;&lt;a href="http://www.drugsyn.org/Mitoxantrone.htm"&gt;DrugSyn.org&lt;/a&gt;&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002377</chemdb-id>
  <dsstox-id>DTXSID4046947</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00008439</susdat-id>
  <iupac>1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-dihydroanthracene-9,10-dione</iupac>
  <moldb-polar-surface-area>163.18</moldb-polar-surface-area>
  <moldb-refractivity>123.53379999999999</moldb-refractivity>
  <moldb-polarizability>48.48888395951877</moldb-polarizability>
  <moldb-rotatable-bond-count>12</moldb-rotatable-bond-count>
  <moldb-acceptor-count>10</moldb-acceptor-count>
  <moldb-donor-count>8</moldb-donor-count>
  <moldb-pka-strongest-acidic>9.77568345472791</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>9.08297868661571</moldb-pka-strongest-basic>
  <moldb-physiological-charge>2</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>0.91</moldb-alogps-logp>
  <moldb-alogps-logs>-2.78</moldb-alogps-logs>
  <moldb-alogps-solubility>7.34e-01 g/l</moldb-alogps-solubility>
</compound>
