<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">42</id>
  <title>T3D0041</title>
  <common-name>Endrin</common-name>
  <description>Endrin has been found as a contaminant throughout the environment, including foodstuffs, fish, human milk, etc.

Endrin belongs to the family of Benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (unsaturated seven-member heterocycle with one oxygen atom replacing a carbon atom.).</description>
  <cas>72-20-8</cas>
  <pubchem-id>3048</pubchem-id>
  <chemical-formula>C12H8Cl6O</chemical-formula>
  <weight>377.870630</weight>
  <appearance>White powder.</appearance>
  <melting-point>226 - 230°C</melting-point>
  <boiling-point></boiling-point>
  <density></density>
  <solubility>0.00025 mg/mL at 25°C</solubility>
  <specific-gravity></specific-gravity>
  <flash-point></flash-point>
  <vapour-pressure></vapour-pressure>
  <route-of-exposure>Oral (L111)</route-of-exposure>
  <target>Gamma-aminobutyric acid receptor subunit alpha-1 (P14867)
Gamma-aminobutyric acid receptor subunit alpha-2 (P47869)
Gamma-aminobutyric acid receptor subunit alpha-3 (P34903)
Gamma-aminobutyric acid receptor subunit alpha-4 (P48169)
Gamma-aminobutyric acid receptor subunit alpha-5 (P31644)
Gamma-aminobutyric acid receptor subunit alpha-6 (Q16445)
Gamma-aminobutyric acid receptor subunit beta-1 (P18505)
Gamma-aminobutyric acid receptor subunit beta-2 (P47870)
Gamma-aminobutyric acid receptor subunit beta-3 (P28472)
Gamma-aminobutyric acid receptor subunit delta (O14764)
Gamma-aminobutyric acid receptor subunit gamma-1 (Q8N1C3)
Gamma-aminobutyric acid receptor subunit gamma-2 (P18507)
Gamma-aminobutyric acid receptor subunit gamma-3 (Q99928)
Gamma-aminobutyric acid receptor subunit pi (O00591)
Gamma-aminobutyric acid receptor subunit rho-1 (P24046)
Gamma-aminobutyric acid receptor subunit rho-2 (P28476)
Gamma-aminobutyric acid receptor subunit rho-3 (A8MPY1)
Gamma-aminobutyric acid receptor subunit theta (Q9UN88)
Sodium/potassium-transporting ATPase subunit alpha-1 (P05023)
Sodium/potassium-transporting ATPase subunit alpha-2 (P50993)
Sodium/potassium-transporting ATPase subunit alpha-3 (P13637) 
Sodium/potassium-transporting ATPase subunit alpha-4 (Q13733)
Sodium/potassium-transporting ATPase subunit beta-1 (P05026)
Sodium/potassium-transporting ATPase subunit beta-2 (P14415)
Sodium/potassium-transporting ATPase subunit beta-3 (P54709)
Sodium/potassium-transporting ATPase gamma chain (P54710)
Calcium-transporting ATPase type 2C member 1 (P98194)
Calcium-transporting ATPase type 2C member 2 (O75185)
Plasma membrane calcium-transporting ATPase 1 (P20020)
Plasma membrane calcium-transporting ATPase 2 (Q01814)
Plasma membrane calcium-transporting ATPase 3 (Q16720)
Plasma membrane calcium-transporting ATPase 4 (P23634)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 (O14983)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 (P16615)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 3 (Q93084)
(T10)</target>
  <mechanism-of-toxicity>Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. Endrin also inhibits Na+ K+ ATPase and Ca2+ and Mg2+ ATPase which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. Endrin also causes increased lipid peroxidation, decreased membrane fluidity, and DNA damage in hepatocytes, but the exact mechanism is unknown. (T10, L112)</mechanism-of-toxicity>
  <metabolism>Endrin is absorbed orally and distributed primarily to the fat and skin. The major biotransformation
product is anti-l 2-hydroxyendrin and the corresponding sulfate, as well as glucuronide metabolites. Anti- and syn-12-hydroxyendrin and 12-ketoendrin are the main toxic metabolites of endrin. Endrin and its metabolites are excreted in urine and feces. (L112)</metabolism>
  <toxicity>LD50: 3 mg/kg (Oral, Rat) (T14) 
LD50: 12 mg/kg (Dermal, Rat) (T14)</toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use-source>Endrin is used as a pesticide. (L111)</use-source>
  <min-risk-level>Intermediate Oral: 0.002 mg/kg/day (L134)
Chronic Oral: 0.0003 mg/kg/day (L134)</min-risk-level>
  <health-effects>Endrin poisoning affects primarily the nerve system. Exposure causes various harmful effects including hyperexcitability, severe central nervous system damage, and death. Endrin is also believed to cause birth defects. (T10, L112)</health-effects>
  <symptoms>Symptoms that may result from endrin poisoning are headaches, dizziness, nervousness, confusion, nausea, vomiting, and convulsions. (L112)</symptoms>
  <treatment>Treatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (L150)</treatment>
  <created-at type="dateTime">2009-03-06T18:57:58Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:20:57Z</updated-at>
  <interacting-proteins></interacting-proteins>
  <wikipedia>http://en.wikipedia.org/wiki/Endrin</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id>DIHYDROKAEMPFEROL-CMPD</biocyc-id>
  <ctd-id>D004732</ctd-id>
  <stitch-id>Endrin</stitch-id>
  <drugbank-id></drugbank-id>
  <pdb-id></pdb-id>
  <actor-id>572</actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>ClC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl</moldb-smiles>
  <moldb-formula>C12H8Cl6O</moldb-formula>
  <moldb-inchi>InChI=1/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2</moldb-inchi>
  <moldb-inchikey>InChIKey=DFBKLUNHFCTMDC-UHFFFAOYNA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">380.909</moldb-average-mass>
  <moldb-mono-mass type="decimal">377.87063112</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>5.2</logp>
  <hmdb-id>HMDB31211</hmdb-id>
  <chembl-id></chembl-id>
  <chemspider-id>2940</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"/>
</compound>
