<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3056</id>
  <title>T3D3014</title>
  <common-name>Dexfenfluramine</common-name>
  <description>Dexfenfluramine, also marketed under the name Redux, is a serotoninergic anorectic drug. It was for some years in the mid-1990s approved by the United States Food and Drug Administration for the purposes of weight loss. However, following multiple concerns about the cardiovascular side-effects of the drug, such approval was withdrawn.</description>
  <cas>3239-44-9</cas>
  <pubchem-id>66265</pubchem-id>
  <chemical-formula>C12H16F3N</chemical-formula>
  <weight>231.123480</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>2.15e-02 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Well-absorbed from the gastrointestinal tract.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Dexfenfluramine binds to the serotonin reuptake pump. This causes inhbition of serotonin reuptake. The increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding behavior located in the hypothalamus. This suppresses the appetite for carbohydrates.</mechanism-of-toxicity>
  <metabolism>Half Life: 17-20 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>A serotoninergic anorectic drug once used for the purposes of weight loss, but pulled out from the global market following multiple concerns about the cardiovascular side-effects of the drug. [Wikipedia]</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Symptoms of overdose include respiratory failure and cardiac arrest leading to death.</symptoms>
  <treatment>General supportive measures for oral drug overdose should be instituted. Measures that have been used in dexfenfluramine overdose cases include aspiration of gastric contents, gastric lavage with activated charcoal, osmotic diuresis, forced acid diuresis, and careful monitoring of CNS or respiratory depression. The effectiveness of dialysis is not known. Patients should be followed closely until there is no further evidence of drug-related CNS effects. No specific therapy for dexfenfluramine overdose is known. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:28:35Z</created-at>
  <updated-at type="dateTime">2026-04-06T09:02:54Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Dexfenfluramine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>439329</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Dexfenfluramine</stitch-id>
  <drugbank-id>DB01191</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CCN[C@@H](C)CC1=CC=CC(=C1)C(F)(F)F</moldb-smiles>
  <moldb-formula>C12H16F3N</moldb-formula>
  <moldb-inchi>InChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3/t9-/m0/s1</moldb-inchi>
  <moldb-inchikey>DBGIVFWFUFKIQN-VIFPVBQESA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">231.2573</moldb-average-mass>
  <moldb-mono-mass type="decimal">231.123484132</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>3.5</logp>
  <hmdb-id>HMDB15322</hmdb-id>
  <chembl-id>CHEMBL248702</chembl-id>
  <chemspider-id>59646</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></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002371</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00115959</susdat-id>
  <iupac>ethyl[(2S)-1-[3-(trifluoromethyl)phenyl]propan-2-yl]amine</iupac>
</compound>
