Esfenvalerate (CED0006217)

Record Information

Version

1.0

Creation Date

2009-06-18 17:03:35 UTC

Update Date

2026-03-26 22:43:17 UTC

SynCED ID

CED0006217

Secondary Accession Numbers

CHEM000894
T3D1036

Identification

Common Name

Esfenvalerate

Class

Small Molecule

Description

Esfenvalerate is a solid exogenous compound with the formula C25H22ClNO3 and an average molecular weight of 419.90 g/mol. Esfenvalerate belongs to the fatty acid esters, a subclass of fatty acyls within the organic compounds. It is utilized as an agrochemical and a pyrethroid ester insecticide. Recorded sources of the compound include agriculture and land management pesticides, drinking water and water supply, and building and construction materials such as tents, canopies, stairs, ramps, and floors. Exposure routes include oral and inhalation. The compound interacts with 31 recorded protein targets, including sodium channel protein type 1 subunit alpha (SCN1A), sodium channel protein type 2 subunit alpha (SCN2A), sodium channel protein type 10 subunit alpha (SCN10A), and sodium channel protein type 11 subunit alpha (SCN11A). As an axonic poison, it prolongs the open phase of sodium channel gates during nerve cell excitation, blocking the closing of the gates and prolonging the return of the membrane potential to its resting state. This leads to nervous system hyperactivity, which can result in death and/or paralysis. Additionally, esfenvalerate targets calcium-transporting ATPase type 2C member 1 (ATP2C1), sarcoplasmic/endoplasmic reticulum calcium ATPase 1 (ATP2A1), and sarcoplasmic/endoplasmic reticulum calcium ATPase 2 (ATP2A2). By inhibiting Ca2+ and Mg2+ ATPase as well as Na+/K+ ATPase, the compound causes an accumulation of intracellular free calcium ions. This process promotes the release of neurotransmitters from storage vesicles, the depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. Other protein targets include beta-secretase 1 (BACE1), C-C motif chemokine 2 (CCL2), ADP-ribosyl cyclase/cyclic ADP-ribose hydrolase 1 (CD38), cytochrome P450 2B6 (CYP2B6), and 11 other proteins.

Contaminant Type

Ester
Ether
Household Toxin
Nitrile
Organic Compound
Organochloride
Pesticide
Pyrethroid
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Esfenvaleric acid	Generator

Chemical Formula

C₂₅H₂₂ClNO₃

Average Molecular Mass

419.900 g/mol

Monoisotopic Mass

419.129 g/mol

CAS Registry Number

66230-04-4

IUPAC Name

(R)-cyano(3-phenoxyphenyl)methyl (2R)-2-(4-chlorophenyl)-3-methylbutanoate

Traditional Name

(R)-cyano(3-phenoxyphenyl)methyl (2R)-2-(4-chlorophenyl)-3-methylbutanoate

SMILES

[H][C@](OC(=O)[C@]([H])(C(C)C)C1=CC=C(Cl)C=C1)(C#N)C1=CC(OC2=CC=CC=C2)=CC=C1

InChI Identifier

InChI=1S/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3/t23-,24+/m0/s1

InChI Key

NYPJDWWKZLNGGM-BJKOFHAPSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Pyrethroids

Alternative Parents

Substituents

Pyrethroid skeleton
Diphenylether
Diaryl ether
Benzyloxycarbonyl
Phenylpropane
Phenoxy compound
Phenol ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Nitrile
Carbonitrile
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organohalogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organochloride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

The pure compound exists as colorless crystals; the technical product as an amber liquid (8).

Experimental Properties

Property	Value
Melting Point	59.5°C
Boiling Point	Not Available
Solubility	2e-06 mg/mL at 25°C [TOMLIN,C (1997)]

Predicted Properties

Property	Value	Source
Water Solubility	0.00082 g/L	ALOGPS
logP	6.3	ALOGPS
logP	6.61	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	10.62	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	59.32 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	116.33 m³·mol⁻¹	ChemAxon
Polarizability	43.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0411900000-576e6a442cd2975d8d87	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0092-2912300000-c930bf4210b4d1f76455	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000t-2900000000-9dbc0feed3da3e356b89	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0010900000-c764c9a2a195b1a81925	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014l-3443900000-457f0845c623ace9f49b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9620000000-7b4eacd6feea01de4b5a	Not Available	View Spectrum
MS	MS Spectrum	splash10-00or-2910000000-b321f70572349c8bdbff	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
458.0 mg/kg	Rat	LD50	Oral	experimental	Not Available	8
2500.0 mg/kg	Rabbit	LD50	Dermal	experimental	Not Available	8
2.93 mg/L	Rat	LC50	Inhalation	experimental	Not Available	8
280.0 Log mg/kg [160:500]	Rat	LD50	oral	predicted	Not Available	Not Available
20.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
30.72 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
160.0 ppm	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
320.0 ppm	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
30.72 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
15.36 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
30.72 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
0.5 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
1.0 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
48.0 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
15.36 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
30.72 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
320.0 ppm	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
160.0 ppm	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
20.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
320.0 ppm	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
160.0 ppm	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
320.0 ppm	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
30.72 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
10.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
20.0 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
50.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
0.05 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
1.0 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
320.0 ppm	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
160.0 ppm	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
48.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
20.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
0.48 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
20.0 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
10.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
320.0 ppm	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
320.0 ppm	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
15.36 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
30.72 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
5.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
80.0 ppm	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
160.0 ppm	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
25.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
50.0 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
20.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
160.0 ppm	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
320.0 ppm	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
50.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
15.36 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
7.68 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
3.84 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
7.68 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
5.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Both 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. (9, 10, 5)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Following dermal exposure to esfenvalerate, 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 esfenvalerate. Paralysis can occur after exposure. (5)

Treatment

Following 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. (3)

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000007	Pesticides?Pesticides are synthetic chemicals designed to prevent, destroy, or control pests that threaten crops and agricultural productivity.	Agriculture & land management	Not Available
CEDs000010	Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.	Agriculture & land management	PubChem
CEDs000115	Drinking water?Drinking water can be a medium for synthetic chemical contamination, often originating from various industrial processes and agricultural practices.	Drinking water & water supply	Not Available
CEDs000181	Ballast water?Ballast water, taken on by ships to maintain stability and balance, often contains a diverse array of microorganisms, including bacteria, viruses, and plankton.	Marine, shipping & aquaculture	PubChem
CEDs000182	Bilge water?Bilge water is a byproduct generated from the accumulation of water in the lowest part of a ship's hull, which may include a mixture of seawater, oil, fuel residues, and various contaminants.	Marine, shipping & aquaculture	PubChem
CEDs000497	Floors?Floors in built environments can be a significant source of synthetic chemical contamination due to the materials and finishes used in their construction.	Building & Construction	PubChem
CEDs000500	Stairs And Ramps?Stairs and ramps in construction are often treated with various synthetic chemicals to enhance durability, slip resistance, and weather resistance.	Building & Construction	PubChem
CEDs000503	Tents Or Canopies?Tents and canopies used in various applications can be a source of synthetic chemical contamination primarily due to the materials from which they are made.	Building & Construction	PubChem
CEDs000514	Discharge Lamps?Discharge lamps, including fluorescent and high-intensity discharge (HID) lamps, are commonly used for lighting applications due to their energy efficiency and brightness.	Electrical & Electronic Equipment	PubChem
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000530	Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.	Electrical & Electronic Equipment	PubChem
CEDs000537	Television Systems?Television systems can be a source of synthetic chemical contamination due to the various materials and components used in their manufacture and operation.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000561	Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.	Household cleaning & consumer products	PubChem
CEDs000579	Manufacture Of Iron Or Steel?The manufacture of iron or steel involves various processes, including smelting, refining, and alloying, which can result in the release of synthetic chemicals and contaminants.	Industrial manufacturing & chemical processing	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000600	Herbicides And Algicides?Herbicides and algicides are synthetic chemicals primarily used to control unwanted plants and algae in various environments.	Agriculture & land management	PubChem
CEDs000602	Molluscicides?Molluscicides are synthetic chemicals specifically designed to control and eliminate mollusks, such as snails and slugs, which can be detrimental to crops and agricultural productivity.	Agriculture & land management	PubChem
CEDs000603	Nematocides?Nematocides are synthetic chemicals specifically designed to control nematodes, which are microscopic roundworms that can cause significant damage to crops and plants.	Agriculture & land management	PubChem
CEDs000604	Pest Attractants?Pest attractants are synthetic chemicals designed to lure specific pests for monitoring or control purposes.	Agriculture & land management	PubChem
CEDs000605	Pest Repellants?Pest repellents, often formulated from synthetic chemicals, are widely used to protect crops from insect infestations and other pests.	Agriculture & land management	PubChem
CEDs000606	Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.	Agriculture & land management	PubChem
CEDs000607	Rodenticides(1)?Rodenticides are synthetic chemicals specifically formulated to control rodent populations, serving as a crucial tool in managing pests that can damage crops and spread diseases.	Agriculture & land management	PubChem
CEDs000608	Rodenticides?Rodenticides are chemical substances specifically designed to control rodent populations by causing death through various mechanisms, including anticoagulation or neurotoxicity.	Agriculture & land management	PubChem
CEDs000609	Aftershave?Aftershave is a grooming product typically used to soothe and protect the skin following shaving.	Personal care & cosmetics	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000613	Depilatories?Depilatories are products designed to remove unwanted hair through the application of synthetic chemicals that break down the protein structure of hair, facilitating its removal.	Personal care & cosmetics	PubChem
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000617	Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000662	Yarns Or Threads?Yarns or threads used in textiles can be a source of synthetic chemical contamination due to the production processes and treatments they undergo.	Textiles, leather & furnishings	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000673	Unmanned Aerial Vehicles?Unmanned Aerial Vehicles (UAVs), commonly known as drones, utilize various synthetic chemicals in their manufacturing, operation, and maintenance processes.	Aviation & Aerospace	PubChem
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	PubChem
CEDs000679	Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.	Agriculture & land management	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000693	Silica Glass?Silica glass, primarily composed of silicon dioxide (SiO2), is widely used in various applications, including windows, glass facades, and insulation materials.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000699	Mining Or Quarrying?Mining and quarrying operations can lead to synthetic chemical contamination through the release of various pollutants associated with the extraction and processing of minerals.	Mining & metal processing	PubChem
CEDs000714	Embossing Machines?Embossing machines are industrial devices used to create raised patterns or designs on materials, including paper and fiber products.	Paper, pulp & fiber products	PubChem
CEDs000727	Printing Machines Or Presses?Printing machines or presses commonly utilize synthetic chemicals such as inks, solvents, and cleaning agents.	Paper, pulp & fiber products	PubChem
CEDs000731	Defecation Help For Disabled Persons?Defecation aids for individuals with disabilities often incorporate various synthetic materials and chemicals in their design, such as plastics, adhesives, and coatings.	Healthcare, pharmaceuticals & veterinary products	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem
CEDs000738	Cooling Circuit Water?Cooling circuit water is utilized in various industrial processes to absorb and dissipate heat generated during operations.	Industrial manufacturing & chemical processing	PubChem
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem
CEDs01157	Foods	Food, food processing & cookware	PMC3447599
CEDs01199	Honey Samples	Food, food processing & cookware	PMC13352592
CEDs01216	Artificial Diet	Food, food processing & cookware	PMC6240031
CEDs01465	Milk Matrix	Food, food processing & cookware	PMC7824741
CEDs02264	Sediment	Aquatic systems & sediments	PMC3114098
CEDs02438	Aquatic Sediments	Aquatic systems & sediments	PMC10008910

Pathways

0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	Prediction Confidence Score 0.286 Applicability Domain 0.319 Statistical Significance 0.163 Supporting Reference Compounds 1130 E-value 1269.25
Click to view 3D structure	15-cis-phytoene desaturase	P26294	Synechococcus elongatus (strain PCC 7942) (Anacystis nidulans R2)	Predicted (SEA)	Prediction Confidence Score 0.282 Applicability Domain 0.282 Low confidence Statistical Significance 0.004 Supporting Reference Compounds 1 E-value 31.5289
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	Prediction Confidence Score 0.28 Applicability Domain 0.319 Statistical Significance 0.0822 Supporting Reference Compounds 593 E-value 639.843
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	Prediction Confidence Score 0.278 Applicability Domain 0.3 Statistical Significance 0.0319 Supporting Reference Compounds 201 E-value 248.728
Click to view 3D structure	Fatty-acid amide hydrolase 1	P97612	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.274 Applicability Domain 0.319 Statistical Significance 0.0204 Supporting Reference Compounds 102 E-value 158.657
Click to view 3D structure	Monoglyceride lipase	Q99685	Humans	Predicted (SEA)	Prediction Confidence Score 0.269 Applicability Domain 0.296 Low confidence Statistical Significance 0.0131 Supporting Reference Compounds 76 E-value 101.827
Click to view 3D structure	Nitric oxide synthase, inducible	P35228	Humans	Predicted (SEA)	Prediction Confidence Score 0.268 Applicability Domain 0.319 Statistical Significance 0.0018 Supporting Reference Compounds 47 E-value 14.0907
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	Prediction Confidence Score 0.266 Applicability Domain 0.296 Low confidence Statistical Significance 0.0695 Supporting Reference Compounds 340 E-value 540.974
Click to view 3D structure	Transient receptor potential cation channel subfamily M member 1	Q2TV84	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.265 Applicability Domain 0.265 Low confidence Statistical Significance 0.0094 Supporting Reference Compounds 1 E-value 73.334
Click to view 3D structure	Fatty-acid amide hydrolase 1	O00519	Humans	Predicted (SEA)	Prediction Confidence Score 0.262 Applicability Domain 0.319 Statistical Significance 0.0487 Supporting Reference Compounds 106 E-value 379.437
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	Prediction Confidence Score 0.262 Applicability Domain 0.273 Low confidence Statistical Significance 0.1226 Supporting Reference Compounds 506 E-value 954.12
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	Prediction Confidence Score 0.261 Applicability Domain 0.273 Low confidence Statistical Significance 0.3887 Supporting Reference Compounds 1245 E-value 3025.77
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	Prediction Confidence Score 0.26 Applicability Domain 0.274 Low confidence Statistical Significance 0.4412 Supporting Reference Compounds 1498 E-value 3434.71
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Predicted (SEA)	Prediction Confidence Score 0.259 Applicability Domain 0.29 Low confidence Statistical Significance 0.127 Supporting Reference Compounds 406 E-value 988.997
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.259 Applicability Domain 0.286 Low confidence Statistical Significance 0.2395 Supporting Reference Compounds 1103 E-value 1864.41
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	Prediction Confidence Score 0.259 Applicability Domain 0.273 Low confidence Statistical Significance 0.4665 Supporting Reference Compounds 1538 E-value 3631.59
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	Prediction Confidence Score 0.258 Applicability Domain 0.273 Low confidence Statistical Significance 0.3417 Supporting Reference Compounds 1301 E-value 2660.11
Click to view 3D structure	Prostaglandin G/H synthase 1	P05979	Ovis aries	Predicted (SEA)	Prediction Confidence Score 0.255 Applicability Domain 0.288 Low confidence Statistical Significance 0.0334 Supporting Reference Compounds 106 E-value 260.328
Click to view 3D structure	Peroxisome proliferator-activated receptor alpha	Q07869	Humans	Predicted (SEA)	Prediction Confidence Score 0.255 Applicability Domain 0.265 Low confidence Statistical Significance 0.0632 Supporting Reference Compounds 127 E-value 492.007
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.268 Low confidence Statistical Significance 0.1366 Supporting Reference Compounds 451 E-value 1063.81
Click to view 3D structure	Polyunsaturated fatty acid 5-lipoxygenase	P09917	Humans	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.288 Low confidence Statistical Significance 0.0527 Supporting Reference Compounds 182 E-value 410.577
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Predicted (SEA)	Prediction Confidence Score 0.253 Applicability Domain 0.265 Low confidence Statistical Significance 0.0878 Supporting Reference Compounds 192 E-value 683.205
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	Prediction Confidence Score 0.253 Applicability Domain 0.275 Low confidence Statistical Significance 0.1096 Supporting Reference Compounds 391 E-value 853.617
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	Prediction Confidence Score 0.252 Applicability Domain 0.271 Low confidence Statistical Significance 0.0503 Supporting Reference Compounds 136 E-value 391.426
Click to view 3D structure	Tyrosine-protein kinase Fyn	P06241	Humans	Predicted (SEA)	Prediction Confidence Score 0.251 Applicability Domain 0.273 Low confidence Statistical Significance 0.3076 Supporting Reference Compounds 707 E-value 2394.72
Click to view 3D structure	Sodium channel protein type 1 subunit alpha	P35498	Humans	Known	This 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 structure	Sodium channel protein type 10 subunit alpha	Q9Y5Y9	Humans	Known	This 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 structure	Sodium channel protein type 11 subunit alpha	Q9UI33	Humans	Known	This 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 structure	Sodium channel protein type 2 subunit alpha	Q99250	Humans	Known	This 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 structure	Sodium channel protein type 3 subunit alpha	Q9NY46	Humans	Known	This 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 structure	Sodium channel protein type 4 subunit alpha	P35499	Humans	Known	This 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 structure	Sodium channel protein type 5 subunit alpha	Q14524	Humans	Known	This 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 structure	Sodium channel protein type 8 subunit alpha	Q9UQD0	Humans	Known	This 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 structure	Sodium channel protein type 9 subunit alpha	Q15858	Humans	Known	This 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 structure	Sodium channel regulatory subunit beta-1	Q07699	Humans	Known	This 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 structure	Sodium channel regulatory subunit beta-2	O60939	Humans	Known	This 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 structure	Sodium channel regulatory subunit beta-3	Q9NY72	Humans	Known	This 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 structure	Sodium channel regulatory subunit beta-4	Q8IWT1	Humans	Known	This 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 structure	Calcium-transporting ATPase type 2C member 1	P98194	Humans	Known	This 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)
Click to view 3D structure	Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	O14983	Humans	Known	This 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)
Click to view 3D structure	Sarcoplasmic/endoplasmic reticulum calcium ATPase 2	P16615	Humans	Known	This 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)
Click to view 3D structure	Beta-secretase 1	P56817	Humans	Known	Not Available
Click to view 3D structure	ADP-ribosyl cyclase/cyclic ADP-ribose hydrolase 1	P28907	Humans	Known	Not Available
Click to view 3D structure	C-C motif chemokine 2	P13500	Humans	Known	Not Available
Click to view 3D structure	Interstitial collagenase	P03956	Humans	Known	Not Available
Click to view 3D structure	Urokinase plasminogen activator surface receptor	Q03405	Humans	Known	Not Available
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 2	O75469	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Known	Not Available
Click to view 3D structure	Retinoic acid receptor alpha	P10276	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Known	Not Available
Click to view 3D structure	Prostaglandin E2 receptor EP2 subtype	P43116	Humans	Known	Not Available
Click to view 3D structure	Vascular cell adhesion protein 1	P19320	Humans	Known	Not Available
Click to view 3D structure	UDP-glucuronosyltransferase 1A1	P22309	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Known	Not Available
Click to view 3D structure	Tumor necrosis factor receptor superfamily member 10B	O14763	Humans	Known	Not Available
Click to view 3D structure	Estrogen receptor	P03372	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Esfenvalerate

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

5361514

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Leng G, Lewalter J, Rohrig B, Idel H: The influence of individual susceptibility in pyrethroid exposure. Toxicol Lett. 1999 Jun 30;107(1-3):123-30. [PubMed: 10414789]
Keller B, Adamski J: RDH12, a retinol dehydrogenase causing Leber's congenital amaurosis, is also involved in steroid metabolism. J Steroid Biochem Mol Biol. 2007 May;104(3-5):190-4. Epub 2007 Mar 23. [PubMed: 17512723]
Wikipedia. Blister agent. Last Updated 24 May 2009. - http://en.wikipedia.org/wiki/Vesicant
Wikipedia. Pyrethroid. Last Updated 8 June 2009. - http://en.wikipedia.org/wiki/Pyrethroid
ATSDR - Agency for Toxic Substances and Disease Registry (2003). Toxicological profile for pyrethrins and pyrethroids. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). - http://www.atsdr.cdc.gov/toxprofiles/tp155.html
Das R et al. Worker Illness Related to Ground Application of Pesticide --- Kern County, California. MMWR 2006;55(17):486-8 - http://www.cdc.gov/mmwr/preview/mmwrhtml/mm5517a4.htm
International Programme on Chemical Safety (IPCS) INCHEM (1990). Environmental Health Criteria for Cyhalothrin. - http://www.inchem.org/documents/ehc/ehc/ehc99.htm
Extension Toxicology Network (1996). Pesticide Information Profile for Esfenvalerate. A Pesticide Information Project of Cooperative Extension Offices of Cornell University, Michigan State University, Oregon State University, and University of California at Davis. - http://extoxnet.orst.edu/pips/esfenval.htm
Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
Hayes WJ Jr. and Laws ER Jr. (eds) (1991). Handbook of Pesticide Toxicology. Volume 3. Classes of Pesticides. New York, NY: Academic Press, Inc.
Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
FAO/WHO (2008). Joint FAO/WHO Meeting on Pesticide Residues: Esfenvalerate.

Esfenvalerate (CED0006217)

Structure for CHEM000894: Esfenvalerate

No pathways found

Structure