Cypermethrin (CED0003558)

Record Information
Version1.0
Creation Date2009-06-18 17:03:35 UTC
Update Date2026-05-14 19:36:25 UTC
Accession NumberCHEM000892
Identification
Common NameCypermethrin
ClassSmall Molecule
Description
Cypermethrin (C22H19Cl2NO3) is an exogenous solid with an average molecular weight of 416.30 g/mol. Cypermethrin belongs to the fatty acid esters, a subclass of fatty acyls within the organic compounds. It is utilized as a pyrethroid ester insecticide, pyrethroid ester acaricide, agrochemical, molluscicide, and biocide (PMC8229483, PMC8587002, PMC10451336, PMC7689789). It is further classified as a pesticide (PMC4817206, PMC8271813, PMC8924399) and an industrial insecticide (PMC11612141). The compound is released from 43 recorded sources, including agriculture and land management pesticides, drinking water, building and construction materials such as floors and roofs, food contact materials, and household cleaning and consumer products. Recorded exposure routes include oral, inhalation, and touch. Cypermethrin targets 35 recorded proteins, including sodium channel protein type 1 subunit alpha (SCN1A), sodium channel protein type 10 subunit alpha (SCN10A), sodium channel protein type 11 subunit alpha (SCN11A), and sodium channel protein type 2 subunit alpha (SCN2A). It acts as an axonic poison that blocks the closing of sodium gates in nerves, prolonging the open phase when a nerve cell is excited. This prolongs the return of the membrane potential to its resting state, leading to nervous system hyperactivity, paralysis, and/or death. Additionally, it targets proteins such as Calcium-transporting ATPase type 2C member 1 (ATP2C1), Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 (ATP2A2), and Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 (ATP2A1). By inhibiting Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, cypermethrin causes intracellular free calcium ions to accumulate, promoting the release of neurotransmitters and the propagation of stimuli throughout the central nervous system. Other protein targets include CYP1A1, CYP1A2, COL3A1, and CYP27B1.
Contaminant Type
  • Ester
  • Ether
  • Household Toxin
  • Human Neurotoxin
  • Insecticide
  • Nitrile
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pyrethroid
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
alpha-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateChEBI
ZetagardKegg
a-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateGenerator
a-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
alpha-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
Α-cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateGenerator
Α-cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
(1S,3S)-(R)-Cyano(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
CymbushHMDB
alpha-CypermethrinHMDB
AlphacypermethrinHMDB
beta-CipermetrinaHMDB
SupercypermethrinHMDB
FastacHMDB
NRDC 149HMDB
Cypermethrin, (1R-(1alpha(r*),3beta))-isomerHMDB
Cypermethrin, (1R-(1alpha(s*),3beta))-isomerHMDB
FendonaHMDB
RipcordHMDB
SherpaHMDB
SupermethrinHMDB
Fastac 50EcHMDB
AlphamethrinHMDB
Cypermethrin, (1alpha(s*),3alpha)-(+-)-isomerHMDB
Chemical FormulaC22H19Cl2NO3
Average Molecular Mass416.297 g/mol
Monoisotopic Mass415.074 g/mol
CAS Registry Number52315-07-8
IUPAC Namecyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Traditional Nameustaad
SMILESCC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC2=CC=CC=C2)=C1
InChI IdentifierInChI=1S/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3
InChI KeyKAATUXNTWXVJKI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentPyrethroids
Alternative Parents
Substituents
  • Pyrethroid skeleton
  • Diphenylether
  • Diaryl ether
  • Benzyloxycarbonyl
  • Phenoxy compound
  • Phenol ether
  • Monocyclic benzene moiety
  • Cyclopropanecarboxylic acid or derivatives
  • Benzenoid
  • Carboxylic acid ester
  • Ketene acetal or derivatives
  • Carboxylic acid derivative
  • Ether
  • Chloroalkene
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • 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
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceLight, amber coloured viscous liquid (11).
Experimental Properties
PropertyValue
Melting Point80.5°C
Boiling PointNot Available
Solubility4e-06 mg/mL at 20°C [WAUCHOPE,RD et al. (1991A)]
Predicted Properties
PropertyValueSource
Water Solubility0.00086 g/LALOGPS
logP5.81ALOGPS
logP5.44ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)10.62ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.32 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity119.09 m³·mol⁻¹ChemAxon
Polarizability40.57 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0512900000-3c26550cde83f141de05Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-1912200000-b3b26bde64fbc63423e0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052e-1900000000-a8aceee4a43e1d313973Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0011900000-32f3cf0f9235364f299fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-3346900000-98416964f4d22c0b7018Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9520000000-1bb5c04c6247a934fc53Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0159-0038900000-53fc8b1c4fc4bcdfd216Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0691-3391400000-39611d4b3cb6d43d0b1dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0api-3890100000-3e4509fe741515b0ca5bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0211900000-db6771eccb17edab98b4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-2860900000-dfb133d3ec704df3980fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9110000000-3657fc947a30f3439e8eNot AvailableView Spectrum
MSMS Spectrumsplash10-02cr-4910000000-8849f1db9e07694cee2fNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityBoth type I and type II pyrethroids 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. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (12, 13, 6)
Carcinogenicity (IARC Classification)Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (3)
Minimum Risk LevelAcute Oral: 0.02 mg/kg/day (Rat) (6)
SymptomsFollowing dermal exposure to cypermethrin, feelings of numbness, itching, burning, stinging, tingling, or warmth may occur, that could last for a few hours. Ddizziness, headache, nausea, muscle twitching, reduced energy, and changes in awareness can reult from inhalation or ingestion of large amounts of cypermethrin. Paralysis can occur after exposure (6).
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. (4)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
250.0mg/kg[250:300]MouseLD50OralexperimentalL873
217.0Log mg/kg[120:390]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
497FloorsBuilding & ConstructionNot Available
498LaddersBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
532SelectorsElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
584BuoysMarine, shipping & aquacultureNot Available
585Canoes And KayaksMarine, shipping & aquacultureNot Available
588Inflatable Life Saving EquipmentMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
590Lifeboat EquipmentMarine, shipping & aquacultureNot Available
591LifeboatsMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
621Chutes And SlidesRecreation & sports surfacesNot Available
622Game AccessoriesRecreation & sports surfacesNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
627Roulette GamesRecreation & sports surfacesNot Available
629SwingsRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
656Snap FastenersTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Monoglyceride lipase structureClick to view 3D structureMonoglyceride lipaseQ99685HumansPredicted (SEA)264.454
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)599.128
Kynurenine--oxoglutarate transaminase 1 structureClick to view 3D structureKynurenine--oxoglutarate transaminase 1Q16773HumansPredicted (SEA)31.8403
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)1739.85
Matrix metalloproteinase-9 structureClick to view 3D structureMatrix metalloproteinase-9P14780HumansPredicted (SEA)1492.99
Click to view 3D structure15-cis-phytoene desaturaseP26294Synechococcus elongatus (strain PCC 7942) (Anacystis nidulans R2)Predicted (SEA)179.442
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)2660.81
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)5580.54
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)1778.39
Matrix metalloproteinase-14 structureClick to view 3D structureMatrix metalloproteinase-14P50281HumansPredicted (SEA)1403.93
Collagenase 3 structureClick to view 3D structureCollagenase 3P45452HumansPredicted (SEA)1876.4
Click to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)796.865
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)1553.79
Macrophage metalloelastase structureClick to view 3D structureMacrophage metalloelastaseP39900HumansPredicted (SEA)1480.69
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)5902.14
Stromelysin-1 structureClick to view 3D structureStromelysin-1P08254HumansPredicted (SEA)1742.19
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)1543.13
Click to view 3D structureRNA-directed RNA polymeraseO39930Hepatitis C VirusPredicted (SEA)163.717
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)3590.33
Cathepsin B structureClick to view 3D structureCathepsin BP07858HumansPredicted (SEA)1396.46
E3 ubiquitin-protein ligase RNF4 structureClick to view 3D structureE3 ubiquitin-protein ligase RNF4P78317HumansPredicted (SEA)190.886
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)2208.74
Procathepsin L structureClick to view 3D structureProcathepsin LP07711HumansPredicted (SEA)1393.66
Cathepsin K structureClick to view 3D structureCathepsin KP43235HumansPredicted (SEA)1177.24
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)6493.71
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansKnownNot Available
Sodium channel protein type 1 subunit alpha structureClick to view 3D structureSodium channel protein type 1 subunit alphaP35498HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Sodium channel protein type 10 subunit alpha structureClick to view 3D structureSodium channel protein type 10 subunit alphaQ9Y5Y9HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Click to view 3D structureSodium channel protein type 11 subunit alphaQ9UI33HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Sodium channel protein type 2 subunit alpha structureClick to view 3D structureSodium channel protein type 2 subunit alphaQ99250HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Sodium channel protein type 3 subunit alpha structureClick to view 3D structureSodium channel protein type 3 subunit alphaQ9NY46HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Sodium channel protein type 4 subunit alpha structureClick to view 3D structureSodium channel protein type 4 subunit alphaP35499HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Sodium channel protein type 5 subunit alpha structureClick to view 3D structureSodium channel protein type 5 subunit alphaQ14524HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Sodium channel protein type 8 subunit alpha structureClick to view 3D structureSodium channel protein type 8 subunit alphaQ9UQD0HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Sodium channel protein type 9 subunit alpha structureClick to view 3D structureSodium channel protein type 9 subunit alphaQ15858HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Sodium channel regulatory subunit beta-1 structureClick to view 3D structureSodium channel regulatory subunit beta-1Q07699HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Sodium channel regulatory subunit beta-2 structureClick to view 3D structureSodium channel regulatory subunit beta-2O60939HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Sodium channel regulatory subunit beta-3 structureClick to view 3D structureSodium channel regulatory subunit beta-3Q9NY72HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Sodium channel regulatory subunit beta-4 structureClick to view 3D structureSodium channel regulatory subunit beta-4Q8IWT1HumansKnownThis pyrethroid exerts its profound effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. This pyrethroid is a axonic poison that block the closing of the sodium gates in the nerves, and, thus, prolongs the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death. Type I Pyrethroid esters (lacking the alpha-cyano substituents) affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT (L857, A560).
Calcium-transporting ATPase type 2C member 1 structureClick to view 3D structureCalcium-transporting ATPase type 2C member 1P98194HumansKnownThis pyrethroid 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. (T10)
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansKnownNot Available
Click to view 3D structureSarcoplasmic/endoplasmic reticulum calcium ATPase 1O14983HumansKnownThis pyrethroid 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. (T10)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 structureClick to view 3D structureSarcoplasmic/endoplasmic reticulum calcium ATPase 2P16615HumansKnownThis pyrethroid 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. (T10)
Urokinase plasminogen activator surface receptor structureClick to view 3D structureUrokinase plasminogen activator surface receptorQ03405HumansKnownNot Available
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansKnownNot Available
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansKnownNot Available
Bile acid receptor structureClick to view 3D structureBile acid receptorQ96RI1HumansKnownNot Available
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansKnownNot Available
Cytochrome P450 2B6 structureClick to view 3D structureCytochrome P450 2B6P20813HumansKnownNot Available
Collagen alpha-1(III) chain structureClick to view 3D structureCollagen alpha-1(III) chainP02461HumansKnownNot Available
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansKnownNot Available
Prostaglandin E2 receptor EP2 subtype structureClick to view 3D structureProstaglandin E2 receptor EP2 subtypeP43116HumansKnownNot Available
Sulfotransferase 2A1 structureClick to view 3D structureSulfotransferase 2A1Q06520HumansKnownNot Available
Click to view 3D structure25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrialO15528HumansKnownNot Available
Vitamin D3 receptor structureClick to view 3D structureVitamin D3 receptorP11473HumansKnownNot Available
Cytochrome P450 1A1 structureClick to view 3D structureCytochrome P450 1A1P04798HumansKnownNot Available
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansKnownNot Available
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansKnownNot Available
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansKnownNot Available
Click to view 3D structureUDP-glucuronosyltransferase 1A1P22309HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDDB13721
HMDB IDHMDB0243566
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCypermethrin
Chemspider ID2809
ChEBI ID4042
PubChem Compound ID2912
Kegg Compound IDC10984
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17420035
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18922205
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20508922
4. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.