<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">5040</id>
  <title>T3D4981</title>
  <common-name>Pioglitazone</common-name>
  <description>Pioglitazone is used for the treatment of diabetes mellitus type 2. Pioglitazone selectively stimulates nuclear receptor peroxisone proliferator-activated receptor gamma (PPAR-gamma). It modulates the transcription of the insulin-sensitive genes involved in the control of glucose and lipid metabolism in the lipidic, muscular tissues and in the liver.</description>
  <cas>111025-46-8</cas>
  <pubchem-id>4829</pubchem-id>
  <chemical-formula>C19H20N2O3S</chemical-formula>
  <weight nil="true"/>
  <appearance nil="true"/>
  <melting-point>183-184 °C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>mg/mL</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Following oral administration, in the fasting state, pioglitazone is first measurable in serum within 30 minutes, with peak concentrations observed within 2 hours. Food slightly delays the time to peak serum concentration to 3 to 4 hours, but does not alter the extent of absorption.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Pioglitazone acts as an agonist at peroxisome proliferator activated receptors (PPAR) in target tissues for insulin action such as adipose tissue, skeletal muscle, and liver. Activation of PPAR-gamma receptors increases the transcription of insulin-responsive genes involved in the control of glucose production, transport, and utilization. In this way, pioglitazone both enhances tissue sensitivity to insulin and reduces hepatic gluconeogenesis. Thus, insulin resistance associated with type 2 diabetes mellitus is improved without an increase in insulin secretion by pancreatic β cells.</mechanism-of-toxicity>
  <metabolism>Hepatic</metabolism>
  <toxicity>Hypogycemia; LD&lt;sub&gt;50&lt;/sub&gt;=mg/kg (orally in rat)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>2A, probably carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>Treatment of Type II diabetes mellitus</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-10-14T21:18:37Z</created-at>
  <updated-at type="dateTime">2026-03-26T18:38:13Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Pioglitazone</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07675</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>8228</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id>C060836</ctd-id>
  <stitch-id nil="true"/>
  <drugbank-id>DB01132</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>CCC1=CN=C(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)C=C1</moldb-smiles>
  <moldb-formula>C19H20N2O3S</moldb-formula>
  <moldb-inchi>InChI=1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23)</moldb-inchi>
  <moldb-inchikey>HYAFETHFCAUJAY-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">356.439</moldb-average-mass>
  <moldb-mono-mass type="decimal">356.119463206</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.3</logp>
  <hmdb-id>HMDB15264</hmdb-id>
  <chembl-id>CHEMBL595</chembl-id>
  <chemspider-id>4663</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;Chandra Khanduri, Yatendra Kumar, Atulya Panda, Suchitra Chakraborty, Mukesh Sharma, &amp;#8220;Process for the preparation of pioglitazone.&amp;#8221; U.S. Patent US20070078170, issued April 05, 2007.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003935</chemdb-id>
  <dsstox-id>DTXSID3037129</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00000599</susdat-id>
  <iupac>5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione</iupac>
</compound>
