<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4814</id>
  <title>T3D4759</title>
  <common-name>Liothyronine</common-name>
  <description>The L-triiodothyronine (T&lt;sub&gt;3&lt;/sub&gt;, liothyronine) thyroid hormone is normally synthesized and secreted by the thyroid gland in much smaller quantities than L-tetraiodothyronine (T&lt;sub&gt;4&lt;/sub&gt;, levothyroxine, L-thyroxine). Most T3 is derived from peripheral monodeiodination of T4 at the 5 position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3. </description>
  <cas>6893-02-3</cas>
  <pubchem-id>5920</pubchem-id>
  <chemical-formula>C15H12I3NO4</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>236-237°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>3.96 mg/L (at 37°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>95% in 4 hours</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>The hormones, T&lt;sub&gt;4&lt;/sub&gt; and T&lt;sub&gt;3&lt;/sub&gt;, are tyrosine-based hormones produced by the thyroid gland. Iodine is an important component in their synthesis. The major form of thyroid hormone in the blood is thyroxine (T&lt;sub&gt;4&lt;/sub&gt;). This is converted to the more active liothyronine form by deiodinases in peripheral tissues. Liothyronine acts on the body to increase the basal metabolic rate, affect protein synthesis and increase the body's sensitivity to catecholamines (such as adrenaline). The thyroid hormones are essential to proper development and differentiation of all cells of the human body. To various extents T&lt;sub&gt;4&lt;/sub&gt; and T&lt;sub&gt;3&lt;/sub&gt; regulate protein, fat and carbohydrate metabolism. Their most pronounced effect is on how human cells use energetic compounds. The thyroid hormone derivatives bind to the thyroid hormone receptors initially to initiate their downstream effects.</mechanism-of-toxicity>
  <metabolism>Half Life: 2.5 days</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Used as replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyrodism during the recovery phase of subacute thyroiditis.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T05:15:14Z</created-at>
  <updated-at type="dateTime">2026-04-05T16:29:08Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Liothyronine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C02465</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>18258</chebi-id>
  <biocyc-id>LIOTHYRONINE</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB00279</drugbank-id>
  <pdb-id>T3</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O</moldb-smiles>
  <moldb-formula>C15H12I3NO4</moldb-formula>
  <moldb-inchi>InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1</moldb-inchi>
  <moldb-inchikey>AUYYCJSJGJYCDS-LBPRGKRZSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">650.9735</moldb-average-mass>
  <moldb-mono-mass type="decimal">650.790038137</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.9</logp>
  <hmdb-id>HMDB00265</hmdb-id>
  <chembl-id>CHEMBL1544</chembl-id>
  <chemspider-id>5707</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;Martin Beasley, David Hause, Irwin Klein, Charles Pamplin, David Reynolds, Kevin Sills, &amp;#8220;Controlled release pharmaceutical compositions of liothyronine and methods of making and using the same.&amp;#8221; U.S. Patent US20060246133, issued November 02, 2006.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003716</chemdb-id>
  <dsstox-id>DTXSID8023216</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00074206</susdat-id>
  <iupac>(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid</iupac>
</compound>
