<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">139</id>
  <title>T3D0138</title>
  <common-name>Chlordecone</common-name>
  <description>Chlordecone is a manufactured insecticide also known as Kepone. It was used mainly on tobacco, ornamental shrubs, bananas, and citrus trees, and in ant and roach traps. However, its use was banned in 1975 due to its toxicity and nature as a persistent organic pollutant. (L601, L602). The LC50 (LC = lethal concentration) is 0.022Р0.095 mg/kg for blue gill and trout. Kepone bioaccumulates in animals by a factors up to a million-fold. Workers with repeated exposure suffer severe convulsions resulting from degradation of the synaptic junctions.</description>
  <cas>143-50-0</cas>
  <pubchem-id>299</pubchem-id>
  <chemical-formula>C10Cl10O</chemical-formula>
  <weight>485.683440</weight>
  <appearance>White powder.</appearance>
  <melting-point>350°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>0.0027 mg/mL at 25 °C [KILZER,L et al. (1979)]</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral(L601) ; inhalation (L601) ; dermal (L601).</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>It is believed that the α-noradrenergic and serotonergic transmitter systems in the central nervous system are the primary neurotransmitter systems affected by chlordecone's neurotoxicity. Chlordecone causes spontaneous neurotransmitter release and increases in free intracellular calcium in synaptosomes by increasing permeability of the plasma membrane, activating voltage-dependent calcium channels, inhibiting of brain mitochondrial calcium uptake, and decreasing the activity of calmodulin-stimulated enzymes and Na+/K+, Mg+, and Ca+ ATPases. This inhibition of membrane ATPases also impairs energy-dependent cellular processes. Chlordecone causes its reproductive effects by binding to the estrogen and androgen receptors. (L601, A213, A214)</mechanism-of-toxicity>
  <metabolism>Chlordecone is well absorbed orally and through inhalation, but may also be absorbed dermally to a lesser extent. It is widely distributed throughout the body and concentrates in the liver, where it is metabolized to chlordecone alcohol by chlordecone reductase. Chlordecone, chlordecone alcohol, and their glucuronide conjugates are slowly excreted in the bile and eliminated in the feces. (L601)</metabolism>
  <toxicity>LD50: 132 mg/kg (Oral, Rat) (T29)
LD50: 410 mg/kg (Percutaneous, Rabbit) (T29)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>2B, possibly carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>Chlordecone is an insecticide. (L601)</use-source>
  <min-risk-level>Acute Oral: 0.01 mg/kg/day (L134)
Intermediate Oral: 0.0005 mg/kg/day (L134)
Chronic Oral: 0.0005 mg/kg/day (L134)</min-risk-level>
  <health-effects>Chlordecone damages the nervous system, skin, liver, and male reproductive system. Animal studies indicate that it may also have harmful kidney effects, developmental effects, and effects on the ability of females to reproduce. (L601)</health-effects>
  <symptoms>Exposure to chlordecone may cause tremors, jerky eye movements, memory loss, headaches, slurred speech, unsteadiness, lack of coordination, loss of weight, rash, enlarged liver, decreased libido, sterility, chest pain, arthralgia, and an increased risk of developing cancer. (L602)</symptoms>
  <treatment>Treatment of chlordecone exposure is symptomatic. (L603)</treatment>
  <created-at type="dateTime">2009-03-06T18:58:09Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:21:11Z</updated-at>
  <interacting-proteins>Albumin (P02768)
(L601)</interacting-proteins>
  <wikipedia>http://en.wikipedia.org/wiki/Kepone</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C01792</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>16548</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id>D007631</ctd-id>
  <stitch-id>Chlordecone</stitch-id>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id>784</actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins>Serum albumin (P02768)
(L601)</transporting-proteins>
  <moldb-smiles>ClC12C(=O)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C4(Cl)C1(Cl)Cl</moldb-smiles>
  <moldb-formula>C10Cl10O</moldb-formula>
  <moldb-inchi>InChI=1/C10Cl10O/c11-2-1(21)3(12)6(15)4(2,13)8(17)5(2,14)7(3,16)9(6,18)10(8,19)20</moldb-inchi>
  <moldb-inchikey>InChIKey=LHHGDZSESBACKH-UHFFFAOYNA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">490.636</moldb-average-mass>
  <moldb-mono-mass type="decimal">485.683441692</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB59603</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>293</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 nil="true"/>
  <structure-image-caption nil="true"/>
</compound>
