<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4834</id>
  <title>T3D4779</title>
  <common-name>Pyrimethamine</common-name>
  <description>One of the folic acid antagonists that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis. </description>
  <cas>58-14-0</cas>
  <pubchem-id>4993</pubchem-id>
  <chemical-formula>C12H13ClN4</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>233.5°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>121 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Well absorbed with peak levels occurring between 2 to 6 hours following administration</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Pyrimethamine inhibits the dihydrofolate reductase of plasmodia and thereby blocks the biosynthesis of purines and pyrimidines, which are essential for DNA synthesis and cell multiplication. This leads to failure of nuclear division at the time of schizont formation in erythrocytes and liver.</mechanism-of-toxicity>
  <metabolism>HepaticHalf Life: 96 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use-source>For the treatment of toxoplasmosis and acute malaria; For the prevention of malaria in areas non-resistant to pyrimethamine</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T05:16:14Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:24:39Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Pyrimethamine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07391</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>8673</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB00205</drugbank-id>
  <pdb-id>CP6</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CCC1=C(C(N)=NC(N)=N1)C1=CC=C(Cl)C=C1</moldb-smiles>
  <moldb-formula>C12H13ClN4</moldb-formula>
  <moldb-inchi>InChI=1S/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7/h3-6H,2H2,1H3,(H4,14,15,16,17)</moldb-inchi>
  <moldb-inchikey>WKSAUQYGYAYLPV-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">248.711</moldb-average-mass>
  <moldb-mono-mass type="decimal">248.082874143</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.69</logp>
  <hmdb-id>HMDB14350</hmdb-id>
  <chembl-id>CHEMBL36</chembl-id>
  <chemspider-id>4819</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/Pyrimethamine.htm"&gt;DrugSyn.org&lt;/a&gt;&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003736</chemdb-id>
  <dsstox-id>DTXSID9021217</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00001824</susdat-id>
  <iupac>5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine</iupac>
  <moldb-polar-surface-area>77.82</moldb-polar-surface-area>
  <moldb-refractivity>71.54200000000002</moldb-refractivity>
  <moldb-polarizability>25.794130782433673</moldb-polarizability>
  <moldb-rotatable-bond-count>2</moldb-rotatable-bond-count>
  <moldb-acceptor-count>4</moldb-acceptor-count>
  <moldb-donor-count>2</moldb-donor-count>
  <moldb-pka-strongest-acidic>17.222043955485603</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>7.773183579634736</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>2.62</moldb-alogps-logp>
  <moldb-alogps-logs>-3.14</moldb-alogps-logs>
  <moldb-alogps-solubility>1.79e-01 g/l</moldb-alogps-solubility>
</compound>
