Fenpropathrin (CHEM001595)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (32)XML
Record Information
Version1.0
Creation Date2009-06-23 18:10:09 UTC
Update Date2026-03-25 19:27:00 UTC
Accession NumberCHEM001595
Identification
Common NameFenpropathrin
ClassSmall Molecule
DescriptionFenpropathrin is a pyrethroid (type 1) insecticide. A pyrethroid is a synthetic chemical compound similar to the natural chemical pyrethrins produced by the flowers of pyrethrums (Chrysanthemum cinerariaefolium and C. coccineum). Pyrethroids are common in commercial products such as household insecticides and insect repellents. In the concentrations used in such products, they are generally harmless to human beings but can harm sensitive individuals. They are usually broken apart by sunlight and the atmosphere in one or two days, and do not significantly affect groundwater quality except for being toxic to fish. Insects with certain mutations in their sodium channel gene may be resistant to pyrethroid insecticides. (3, 2)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Household Toxin
  • Nitrile
  • Organic Compound
  • Pesticide
  • Pyrethroid
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-FenpropathrinChEBI
2,2,3,3-Tetramethylcyclopropanecarboxylic acid cyano(3-phenoxyphenyl)methyl esterChEBI
MeothrinChEBI
2,2,3,3-Tetramethylcyclopropanecarboxylate cyano(3-phenoxyphenyl)methyl esterGenerator
Fenpropathrin, (R)-isomerMeSH
Fenpropathrin, (S)-isomerMeSH
Fenpropathrin, (+-)-isomerMeSH
Chemical FormulaC22H23NO3
Average Molecular Mass349.423 g/mol
Monoisotopic Mass349.168 g/mol
CAS Registry Number39515-41-8
IUPAC Namecyano(3-phenoxyphenyl)methyl 2,2,3,3-tetramethylcyclopropane-1-carboxylate
Traditional NameRody
SMILESCC1(C)C(C(=O)OC(C#N)C2=CC=CC(OC3=CC=CC=C3)=C2)C1(C)C
InChI IdentifierInChI=1S/C22H23NO3/c1-21(2)19(22(21,3)4)20(24)26-18(14-23)15-9-8-12-17(13-15)25-16-10-6-5-7-11-16/h5-13,18-19H,1-4H3
InChI KeyXQUXKZZNEFRCAW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentDiphenylethers
Alternative Parents
Substituents
  • Diphenylether
  • Diaryl ether
  • Benzyloxycarbonyl
  • Phenoxy compound
  • Phenol ether
  • Cyclopropanecarboxylic acid or derivatives
  • Carboxylic acid ester
  • Nitrile
  • Carbonitrile
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceYellow to brown liquid or solid (6).
Experimental Properties
PropertyValue
Melting Point47°C
Boiling PointNot Available
Solubility0.00033 mg/mL at 25°C [SHIU,WY et al. (1990)]
Predicted Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP5.24ALOGPS
logP4.85ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)10.62ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.32 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.52 m³·mol⁻¹ChemAxon
Polarizability37.5 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-8190000000-3ab2c641009bca73eff0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0309000000-0b8bf0e2f0cbbe1cdc7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-1915000000-5daae9be0a3966abf54fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-9700000000-3f5a0f83bca058f8e7bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-2ac2533677ffc3559eb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0129000000-fcceee24fcc0851f1790Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-5910000000-c222e81ab53f32f5255cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-5139000000-0f04f4e25aa15f10dab8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6s-2295000000-5e10090c5d949e231d79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9340000000-a05130253f7bf6ef49c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0809000000-a13521bafe65cceaf5e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006t-2549000000-cfbfa4d823a487546f78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-9210000000-027325d32fb2ad2da9dfSpectrum
MSMass Spectrum (Electron Ionization)splash10-055e-9310000000-3f3f82abaab71f61940eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureInhalation (4) ; oral (4) ; dermal (4) ; eye contact (4).
Mechanism of ToxicityPyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. (7, 4)
MetabolismFenpropathrin has been shown to be well absorbed after oral administration, extensively metabolized, and eliminated as polar conjugates in urine. The main route of metabolism was, as anticipated, via hydrolysis of the ester linkage. The cyclopropane-carboxylic acid moiety was subsequently excreted via the urine as the glucuronide conjugate. (4)
Toxicity ValuesLD50: 70.6 mg/kg (Oral, Rat) (9)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPyrethroids are used as insecticides. (4)
Minimum Risk LevelNot Available
Health EffectsAt high doses, signs of poisoning attributable to fenpropathrin include profuse salivation and pulmonary edema, clonic seizures, opisthotonos (i.e., the spine is bent forward such that a supine body rests on its head and heels), coma, and death. At lower doses, commonly observed effects include paresthesia and erythema. (5)
SymptomsFollowing dermal exposure to fenpropathrin, feelings of numbness, itching, burning, stinging, tingling, or warmth may occur, that could last for a few hours. Dizziness, headache, nausea, muscle twitching, reduced energy, and changes in awareness can result from inhalation or ingestion of large amounts of fenpropathrine. Paralysis can occur after exposure. (4)
TreatmentFollowing oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. 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. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (8)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0252216
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFenpropathrin
Chemspider ID43074
ChEBI ID39353
PubChem Compound IDNot Available
Kegg Compound IDC18411
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10552511
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12952428
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18808096
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20640937
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21052987
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21181490
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21370394
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21381771
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21404693
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21503692
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21727000
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21785877
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=8571384