<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2785</id>
  <title>T3D2743</title>
  <common-name>Mitomycin</common-name>
  <description>Mitomycin is only found in individuals that have used or taken this drug. It is an antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional alkylating agents causing cross-linking of DNA and inhibition of DNA synthesis. Mitomycin is activated in vivo to a bifunctional and trifunctional alkylating agent. Binding to DNA leads to cross-linking and inhibition of DNA synthesis and function. Mitomycin is cell cycle phase-nonspecific.</description>
  <cas>50-07-7</cas>
  <pubchem-id>5746</pubchem-id>
  <chemical-formula>C15H18N4O5</chemical-formula>
  <weight>334.127720</weight>
  <appearance>White powder.</appearance>
  <melting-point>&gt;360°C</melting-point>
  <boiling-point>534°C</boiling-point>
  <density nil="true"/>
  <solubility>Soluble (8430 mg/L)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Intravesical, erratic, intravenous.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Mitomycin is activated in vivo to a bifunctional and trifunctional alkylating agent. Binding to DNA leads to cross-linking and inhibition of DNA synthesis and function. Mitomycin is cell cycle phase-nonspecific.</mechanism-of-toxicity>
  <metabolism>Primarily hepatic, some in various other tissues.
Route of Elimination: Approximately 10% of a dose of mitomycin is excreted unchanged in the urine.
Half Life: 8-48 min</metabolism>
  <toxicity>LD50: 23 mg/kg (Oral, Mouse) (A308)
LD50: 30 mg/kg (Oral, Rat) (A308)</toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>2B, possibly carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>For treatment of malignant neoplasm of lip, oral cavity, pharynx, digestive organs, peritoneum, female breast, and urinary bladder. Also used as an adjunct to ab externo glaucoma surgery.</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>Mitomycin C causes delayed bone marrow toxicity and therefore it is usually administered at 6-weekly intervals. Prolonged use may result in permanent bone-marrow damage. It may also cause lung fibrosis and renal damage.</health-effects>
  <symptoms></symptoms>
  <treatment></treatment>
  <created-at type="dateTime">2009-07-21T20:26:32Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:25:18Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Mitomycin</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C06681</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>27504</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id>Mitomycin</stitch-id>
  <drugbank-id>DB00305</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CO[C@]12[C@H]3N[C@H]3CN1C1=C([C@H]2COC(N)=O)C(=O)C(N)=C(C)C1=O</moldb-smiles>
  <moldb-formula>C15H18N4O5</moldb-formula>
  <moldb-inchi>InChI=1S/C15H18N4O5/c1-5-9(16)12(21)8-6(4-24-14(17)22)15(23-2)13-7(18-13)3-19(15)10(8)11(5)20/h6-7,13,18H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7+,13+,15-/m1/s1</moldb-inchi>
  <moldb-inchikey>NWIBSHFKIJFRCO-WUDYKRTCSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">334.3272</moldb-average-mass>
  <moldb-mono-mass type="decimal">334.127719706</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-0.4</logp>
  <hmdb-id>HMDB14450</hmdb-id>
  <chembl-id>CHEMBL105</chembl-id>
  <chemspider-id>5544</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;Leslie Jimenez, Zheng Wang, &amp;#8220;Synthesis of mitomycin and its analogs.&amp;#8221; U.S. Patent US5523411, issued June, 1972.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002165</chemdb-id>
  <dsstox-id>DTXSID2020898</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00108399</susdat-id>
  <iupac>[(4S,6S,7R,8S)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0^{2,7}.0^{4,6}]trideca-1(9),11-dien-8-yl]methyl carbamate</iupac>
  <moldb-polar-surface-area>146.89</moldb-polar-surface-area>
  <moldb-refractivity>83.2689</moldb-refractivity>
  <moldb-polarizability>32.771578111969</moldb-polarizability>
  <moldb-rotatable-bond-count>4</moldb-rotatable-bond-count>
  <moldb-acceptor-count>7</moldb-acceptor-count>
  <moldb-donor-count>3</moldb-donor-count>
  <moldb-pka-strongest-acidic>-0.3015826322633606</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>6.798030276661671</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>4</moldb-number-of-rings>
  <moldb-alogps-logp>-0.55</moldb-alogps-logp>
  <moldb-alogps-logs>-1.52</moldb-alogps-logs>
  <moldb-alogps-solubility>1.01e+01 g/l</moldb-alogps-solubility>
</compound>
