<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3919</id>
  <title>T3D3864</title>
  <common-name>Indoxacarb</common-name>
  <description>Indoxacarb is an oxadiazine pesticide developed by DuPont that acts against lepidopteran larvae. It is marketed under the names Indoxacarb Technical Insecticide, Steward Insecticide and Avaunt Insecticide. It is also used as the active ingredient in DuPont's line of commercial pesticides: Advion and Arilon.</description>
  <cas>173584-44-6</cas>
  <pubchem-id>107720</pubchem-id>
  <chemical-formula>C22H17ClF3N3O7</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Ingestion</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>It is thought that indoxacarb's aromatic metabolites biotransform to active intermediates that produce methemoglobin (A15207). The mechanism of indoxacarb-induced renal injury and metabolic acidosis in humans remains unclear. (A15207) It has been suggested that acute kidney injury results from indoxacarb-induced circulatory shock (A15206). Rhabdomyolysis may have been induced by methemoglobinemia (A15206).</mechanism-of-toxicity>
  <metabolism>Metabolism in rats after oral dosing noted that most of the dose was excreted within 96 h. In urine, metabolites were cleaved products (indane or trifluoromethoxyphenyl ring products), whereas in feces, major metabolites retained both these moieties. Major metabolic reactions included hydroxylation of the indane ring, hydrolysis of the carboxymethyl group from the amino nitrogen, and opening of the oxadiazine ring, which gave rise to cleaved products. (A15205)</metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>This is a man-made compound that is used as an insecticide.</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>Acute ingestion of indoxacarb causes methemoglobinemia (A15205). Indoxacarb poisoning has also been associated with acute kidney injury, involving acute renal failure and severe metabolic acidosis (A15207). A case involving rhabdomyolysis, in addition to methemoglobinemia and acute kidney injury, has also been reported (A15206).</health-effects>
  <symptoms>Human toxicity includes eye irritation, blurred vision, skin sensitization with allergic rashes, alteration in blood cell counts, and/or anemia (A15205). As methemoglobin levels increase, typical symptoms develop. Levels of 20 – 50% will cause respiratory distress, dizziness, headache, and fatigue as in this case. Lethargy and stupor develop at levels around 50% and death may occur around 70%. (A15206)</symptoms>
  <treatment>Very few case reports of acute indoxacarb ingestion are reported in the literature. Reported treatments commonly involve treatment with methylene blue (A15205) (A15207) (A15206). Severe metabolic acidosis was treated with continuous veno-venous hemofiltration (CVVHF) and bicarbonate (NaHCO3) (A15207).</treatment>
  <created-at type="dateTime">2013-04-25T07:56:52Z</created-at>
  <updated-at type="dateTime">2026-04-06T04:06:06Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia></wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C18569</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>38630</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id></stitch-id>
  <drugbank-id></drugbank-id>
  <pdb-id></pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>COC(=O)N(C(=O)N1CO[C@]2(CC3=C(C=CC(Cl)=C3)C2=N1)C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1</moldb-smiles>
  <moldb-formula>C22H17ClF3N3O7</moldb-formula>
  <moldb-inchi>InChI=1S/C22H17ClF3N3O7/c1-33-18(30)21-10-12-9-13(23)3-8-16(12)17(21)27-28(11-35-21)19(31)29(20(32)34-2)14-4-6-15(7-5-14)36-22(24,25)26/h3-9H,10-11H2,1-2H3/t21-/m0/s1</moldb-inchi>
  <moldb-inchikey>VBCVPMMZEGZULK-NRFANRHFSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">527.834</moldb-average-mass>
  <moldb-mono-mass type="decimal">527.070712235</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp></logp>
  <hmdb-id></hmdb-id>
  <chembl-id>CHEMBL197676</chembl-id>
  <chemspider-id>96889</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>CHEM002825</chemdb-id>
  <dsstox-id>DTXSID1032690</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00098526</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>106.97000000000001</moldb-polar-surface-area>
  <moldb-refractivity>112.01350000000001</moldb-refractivity>
  <moldb-polarizability>46.55534719123111</moldb-polarizability>
  <moldb-rotatable-bond-count>6</moldb-rotatable-bond-count>
  <moldb-acceptor-count>7</moldb-acceptor-count>
  <moldb-donor-count>0</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic>-1.434421712212473</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>4</moldb-number-of-rings>
  <moldb-alogps-logp>3.63</moldb-alogps-logp>
  <moldb-alogps-logs>-5.41</moldb-alogps-logs>
  <moldb-alogps-solubility>2.04e-03 g/l</moldb-alogps-solubility>
</compound>
