<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2903</id>
  <title>T3D2861</title>
  <common-name>Daunorubicin</common-name>
  <description>Daunorubicin is only found in individuals that have used or taken this drug. It is a very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of leukemia and other neoplasms. [PubChem]Daunorubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Daunorubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.</description>
  <cas>20830-81-3</cas>
  <pubchem-id>30323</pubchem-id>
  <chemical-formula>C27H29NO10</chemical-formula>
  <weight>527.179150</weight>
  <appearance>White powder.</appearance>
  <melting-point>208-209°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>39.2 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Intravenous</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Daunorubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Daunorubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.</mechanism-of-toxicity>
  <metabolism>HepaticRoute of Elimination: Twenty-five percent of an administered dose of daunorubicin hydrochloride is eliminated in an active form by urinary excretion and an estimated 40% by biliary excretion.Half Life: 18.5 hours</metabolism>
  <toxicity>LD50=20 mg/kg (mice, IV); LD50=13 mg/kg (rat, IV)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>2B, possibly carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>For remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Antibiotic resistance.  Toxic manifestations of Daunorubicin include bone marrow depression, stomatitis, alopecia, gastrointestinal disturbances, and dermatological manifestations. Cardiac toxicity is a pecular effect. (A723)</health-effects>
  <symptoms>symptoms include gastrointestinal disturbances. (A723)</symptoms>
  <treatment>Infuse 10 to 20 mL/kg isotonic fluid. If hypotension persists, administer dopamine. (A704)</treatment>
  <created-at type="dateTime">2009-07-21T20:27:25Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:52Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Daunorubicin</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C01907</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>4330</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Daunorubicin</stitch-id>
  <drugbank-id>DB00694</drugbank-id>
  <pdb-id>DM1</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H][C@]1(N)C[C@]([H])(O[C@@]2([H])C[C@@](O)(CC3=C(O)C4=C(C(O)=C23)C(=O)C2=C(C=CC=C2OC)C4=O)C(C)=O)O[C@@]([H])(C)[C@@]1([H])O</moldb-smiles>
  <moldb-formula>C27H29NO10</moldb-formula>
  <moldb-inchi>InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1</moldb-inchi>
  <moldb-inchikey>InChIKey=STQGQHZAVUOBTE-VGBVRHCVSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">527.5199</moldb-average-mass>
  <moldb-mono-mass type="decimal">527.179146153</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.83</logp>
  <hmdb-id>HMDB14832</hmdb-id>
  <chembl-id>CHEMBL178</chembl-id>
  <chemspider-id>28163</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;Sylvie Pinnert, Leon Ninet, Jean Preud&amp;#8217;Homme, &amp;#8220;Antibiotic daunorubicin and its preparation.&amp;#8221; U.S. Patent US3989598, issued March, 1965.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
