<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4791</id>
  <title>T3D4736</title>
  <common-name>Fludarabine</common-name>
  <description>Fludarabine (marketed as fludarabine phosphate under the trade name Fludara) is a chemotherapy drug used in the treatment of hematological malignancies. </description>
  <cas>75607-67-9</cas>
  <pubchem-id>30751</pubchem-id>
  <chemical-formula>C10H13FN5O7P</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>260°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>3.53 mg/ml</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Bioavailability is 55% following oral administration.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Fludarabine phosphate is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. This metabolite appears to act by inhibiting DNA polymerase alpha, ribonucleotide reductase and DNA primase, thus inhibiting DNA synthesis. The mechanism of action of this antimetabolite is not completely characterized and may be multi-faceted.</mechanism-of-toxicity>
  <metabolism>Half Life: 20 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of adult patients with B-cell chronic lymphocytic leukemia (CLL) who have not responded to or whose disease has progressed during treatment with at least one standard alkylating-agent containing regimen</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T05:14:03Z</created-at>
  <updated-at type="dateTime">2026-03-26T21:33:38Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Fludarabine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id nil="true"/>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB01073</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>NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]3O)C2=NC(F)=N1</moldb-smiles>
  <moldb-formula>C10H13FN5O7P</moldb-formula>
  <moldb-inchi>InChI=1S/C10H13FN5O7P/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,14,15)(H2,19,20,21)/t3-,5-,6+,9-/m1/s1</moldb-inchi>
  <moldb-inchikey>GIUYCYHIANZCFB-FJFJXFQQSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">365.2117</moldb-average-mass>
  <moldb-mono-mass type="decimal">365.053662512</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-2.8</logp>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL1568</chembl-id>
  <chemspider-id>28532</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;John G. Bauman, Randolph C. Wirsching, &amp;#8220;Process for the preparation of fludarabine or fludarabine phosphate from guanosine.&amp;#8221; U.S. Patent US5602246, issued January, 1992.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003693</chemdb-id>
  <dsstox-id>DTXSID4039657</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00003718</susdat-id>
  <iupac>{[(2R,3S,4S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac>
</compound>
