<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">618</id>
  <title>T3D0617</title>
  <common-name>Chlorbenzylate</common-name>
  <description>Chlorobenzilate is a chlorinated hydrocarbon compound. It is used for mite control on citrus crops and in beehives. It has narrow insecticidal action, killing only ticks and mites. Products are available as emulsifiable concentrates or wettable powder formulations (L957).</description>
  <cas>510-15-6</cas>
  <pubchem-id>10522</pubchem-id>
  <chemical-formula>C16H14Cl2O3</chemical-formula>
  <weight>324.032000</weight>
  <appearance>Technical chlorobenzilate, a brownish liquid, contains approximately 90% active compound. Pure chlorobenzilate is a yellow solid (L957).</appearance>
  <melting-point>37°C</melting-point>
  <boiling-point></boiling-point>
  <density></density>
  <solubility>0.013 mg/mL at 20°C [FURER,R &amp; GEIGER,M (1977)]</solubility>
  <specific-gravity></specific-gravity>
  <flash-point></flash-point>
  <vapour-pressure></vapour-pressure>
  <route-of-exposure>Dermal  (L957</route-of-exposure>
  <target>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>At least four mechanisms, possibly all functioning simultaneously.
DDT reduces potassium transport across the membrane. DDT alters the porous channels through which sodium ions pass. These channels activate (open) normally but are inactivated (closed) slowly, thus interfering with the active transport of sodium out of the nerve axon during repolarization. DDT inhibits neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase, and Ca2+-ATPase which play vital roles in neuronal repolarization. DDT also inhibits the ability of calmodulin, a calcium mediator in nerves, to transport calcium ions that are essential for the release of neurotransmitters. All these inhibited functions reduce the rate of depolarization and increase the sensitivity of neurons to small stimuli that would not elicit a response in a fully depolarized neuron. (T10)</mechanism-of-toxicity>
  <metabolism>Chlorobenzilate is metabolized by liver homogenates to para,para'-dichlorobenzilic acid; para, para'-dichlorobenzyhydrol; para-chlorobenzoic acid, and para, para'-dichlorobenzophenone. It is excreted in the urine (T35).</metabolism>
  <toxicity>LD50: 2784-3880 mg/kg (Oral, Rat) (L957)
LD50: &gt;10 000 mg/kg (Dermal, Rat) (L957)
LD50: &gt;10 000 mg/kg (Dermal, Rabbit) (L957)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use-source>Chlorobenzilate is used for mite control on citrus crops and in beehives. It has narrow insecticidal action, killing only ticks and mites (L957).</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Nervous tension, liver and kidney damage, abnormal electrical activity of the brain (T10, L957, T35)</health-effects>
  <symptoms>Symptoms of chlrobenzilate poisoning include muscle pains, ataxia, mild delirium, fever, and mental status changes progressing to a tonic-clonic seizure. Nausea, vomiting, and diarrhea may follow ingestion (T35, A572).</symptoms>
  <treatment>In case of ingestion, consider cautious gastric lavage; it must be weighed against potential complications of bleeding or perforation. Activated charcoal binds most toxic agents and can decrease their systemic absorption if administered soon after ingestion. In case of inhalation, move patient to fresh air. Monitor for respiratory distress, and if cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes if the exposure occurred through eye contact. In case of dermal exposure, remove contaminated clothing and jewellery. Wash skin and hair thoroughly; do two soap and water washings. Leather absorbs pesticides. Hence, leather should not be worn in the presence of pesticides and all contaminated leather should be discarded. (T36)</treatment>
  <created-at type="dateTime">2009-03-06T18:59:14Z</created-at>
  <updated-at type="dateTime">2026-03-27T00:43:36Z</updated-at>
  <interacting-proteins>No data.</interacting-proteins>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C14574</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id>C004659</ctd-id>
  <stitch-id>Chlorbenzylate</stitch-id>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id>301</actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CCOC(=O)C(O)(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1</moldb-smiles>
  <moldb-formula>C16H14Cl2O3</moldb-formula>
  <moldb-inchi>InChI=1S/C16H14Cl2O3/c1-2-21-15(19)16(20,11-3-7-13(17)8-4-11)12-5-9-14(18)10-6-12/h3-10,20H,2H2,1H3</moldb-inchi>
  <moldb-inchikey>RAPBNVDSDCTNRC-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">325.187</moldb-average-mass>
  <moldb-mono-mass type="decimal">324.031999728</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL539904</chembl-id>
  <chemspider-id>10085</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>CHEM000549</chemdb-id>
  <dsstox-id>DTXSID9020299</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>ethyl 2,2-bis(4-chlorophenyl)-2-hydroxyacetate</iupac>
</compound>
