Indoxacarb (CHEM002825)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (30)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:52 UTC
Update Date2026-04-06 04:06:06 UTC
Accession NumberCHEM002825
Identification
Common NameIndoxacarb
ClassSmall Molecule
DescriptionIndoxacarb 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.
Contaminant Sources
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Carbamate
  • Ester
  • Ether
  • Household Toxin
  • Insecticide
  • Organic Compound
  • Organochloride
  • Organofluoride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
StewardChEBI
DPX-MP062MeSH
Chemical FormulaC22H17ClF3N3O7
Average Molecular Mass527.834 g/mol
Monoisotopic Mass527.071 g/mol
CAS Registry Number173584-44-6
IUPAC Namemethyl (4aS)-7-chloro-2-{[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]carbonyl}-2H,3H,4aH,5H-indeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate
Traditional Nameavent
SMILESCOC(=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
InChI IdentifierInChI=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
InChI KeyVBCVPMMZEGZULK-NRFANRHFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylcarbamic acid esters
Direct ParentPhenylcarbamic acid esters
Alternative Parents
Substituents
  • Phenylcarbamic acid ester
  • N-phenylurea
  • Indane
  • Phenoxy compound
  • Phenol ether
  • Aryl chloride
  • Aryl halide
  • Semicarbazone
  • Semicarbazide
  • Carbamic acid ester
  • Methyl ester
  • Trihalomethane
  • Carboxylic acid ester
  • Carbonic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Alkyl fluoride
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Alkyl halide
  • Halomethane
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.002 g/LALOGPS
logP3.63ALOGPS
logP5.39ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area106.97 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity112.01 m³·mol⁻¹ChemAxon
Polarizability46.56 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000090000-4f97f366921e4e449d66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0010490000-64ebc67677a69262a6caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hh0-2071900000-c8c4c27acbaca5b8f710Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000290000-18efe8af03ec017c9a01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05dj-0094750000-0363aac7f48a31b40794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00sr-1190300000-9d44e9261a77b7f15427Spectrum
Toxicity Profile
Route of ExposureIngestion
Mechanism of ToxicityIt is thought that indoxacarb's aromatic metabolites biotransform to active intermediates that produce methemoglobin (3). The mechanism of indoxacarb-induced renal injury and metabolic acidosis in humans remains unclear. (3) It has been suggested that acute kidney injury results from indoxacarb-induced circulatory shock (2). Rhabdomyolysis may have been induced by methemoglobinemia (2).
MetabolismMetabolism 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. (1)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is a man-made compound that is used as an insecticide.
Minimum Risk LevelNot Available
Health EffectsAcute ingestion of indoxacarb causes methemoglobinemia (1). Indoxacarb poisoning has also been associated with acute kidney injury, involving acute renal failure and severe metabolic acidosis (3). A case involving rhabdomyolysis, in addition to methemoglobinemia and acute kidney injury, has also been reported (2).
SymptomsHuman toxicity includes eye irritation, blurred vision, skin sensitization with allergic rashes, alteration in blood cell counts, and/or anemia (1). 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%. (2)
TreatmentVery few case reports of acute indoxacarb ingestion are reported in the literature. Reported treatments commonly involve treatment with methylene blue (1) (3) (2). Severe metabolic acidosis was treated with continuous veno-venous hemofiltration (CVVHF) and bicarbonate (NaHCO3) (3).
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIndoxacarb
Chemspider IDNot Available
ChEBI ID38630
PubChem Compound ID107720
Kegg Compound IDC18569
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available