<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4827</id>
  <title>T3D4772</title>
  <common-name>Stavudine</common-name>
  <description>A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV. </description>
  <cas>3056-17-5</cas>
  <pubchem-id>18283</pubchem-id>
  <chemical-formula>C10H12N2O4</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>159-160°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>5-10 g/100 mL at 21°C</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Following oral administration, stavudine is rapidly absorbed (bioavailability is 68-104%).</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Stavudine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA.</mechanism-of-toxicity>
  <metabolism>Phosphorylated intracellularly to stavudine triphosphate, the active substrate for HIV-reverse transcriptase.Half Life: 0.8-1.5 hours (in adults)</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 human immunovirus (HIV) infections.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Side effects include peripheral neuropathy tingling, burning, numbness, or pain in the hands or feet), fatal lactic acidosis has been reported in patients treated with stavudine (ZERIT) in combination with other antiretroviral agents, severe liver enlargement, inflammation (pain and swelling) of the liver, and liver failure.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T05:15:56Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:26:57Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Stavudine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07312</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>63581</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB00649</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>[H][C@]1(CO)O[C@]([H])(C=C1)N1C=C(C)C(O)=NC1=O</moldb-smiles>
  <moldb-formula>C10H12N2O4</moldb-formula>
  <moldb-inchi>InChI=1S/C10H12N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h2-4,7-8,13H,5H2,1H3,(H,11,14,15)/t7-,8+/m0/s1</moldb-inchi>
  <moldb-inchikey>InChIKey=XNKLLVCARDGLGL-JGVFFNPUSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">224.2133</moldb-average-mass>
  <moldb-mono-mass type="decimal">224.079706882</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-0.72</logp>
  <hmdb-id>HMDB14787</hmdb-id>
  <chembl-id>CHEMBL991</chembl-id>
  <chemspider-id>17270</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;Purna Chandra Ray, Jagan Mohana Chary Tummanapalli, Seeta Ramanjaneyulu Gorantla, &amp;#8220;Process for the Large Scale Production of Stavudine.&amp;#8221; U.S. Patent US20080312428, issued December 18, 2008.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
