Tetramethrin (CED0010011)

Record Information

Version

1.0

Creation Date

2009-06-18 17:03:35 UTC

Update Date

2026-05-14 19:36:47 UTC

SynCED ID

CED0010011

Secondary Accession Numbers

CHEM000886
T3D1028

Identification

Common Name

Tetramethrin

Class

Small Molecule

Description

Tetramethrin is a solid compound with the formula C19H25NO4 and an average molecular weight of 331.41 g/mol. Tetramethrin belongs to the isoindolines, a subclass of isoindoles and derivatives within the organic compounds. This exogenous substance is used industrially as a biocide and biologically as a pyrethroid ester insecticide. Recorded sources of the compound include indoor air, drinking water, tents or canopies, the preparation of malt, and electrical and electronic equipment such as coils, amplifiers, and discharge lamps. Exposure routes include oral and inhalation. The compound interacts with 25 recorded protein targets. These include the 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). As an axonic poison, this pyrethroid blocks the closing of sodium gates in the nerves and prolongs the open phase of the sodium channel gates during nerve cell excitation. This prolongs the return of the membrane potential to its resting state, leading to nervous system hyperactivity, which can result in death and/or paralysis. Additionally, it targets 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 Ca2+ and Mg2+ ATPase as well as Na+/K+ ATPase, it causes intracellular free calcium ions to accumulate, promoting the release of neurotransmitters from storage vesicles and the propagation of stimuli throughout the central nervous system. Other targets include C-C motif chemokine 2 (CCL2), cytochrome P450 2B6 (CYP2B6), cytochrome P450 2C19 (CYP2C19), and cytochrome P450 3A4 (CYP3A4).

Contaminant Type

Amide
Amine
Ester
Ether
Household Toxin
Organic Compound
Pesticide
Pyrethroid
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Neo-pynamin	ChEBI
Neopinamin	ChEBI
Phthalthrin	ChEBI
Neopinamine	MeSH
2,2-Dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic acid, ester with N-(hydroxymethyl)-1-cyclo hexene 1,2-dicarboximide	MeSH
Neopynamin	MeSH

Chemical Formula

C₁₉H₂₅NO₄

Average Molecular Mass

331.406 g/mol

Monoisotopic Mass

331.178 g/mol

CAS Registry Number

7696-12-0

IUPAC Name

(1,3-dioxo-2,3,4,5,6,7-hexahydro-1H-isoindol-2-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

Traditional Name

tetramethrin

SMILES

CC(C)=CC1C(C(=O)OCN2C(=O)C3=C(CCCC3)C2=O)C1(C)C

InChI Identifier

InChI=1S/C19H25NO4/c1-11(2)9-14-15(19(14,3)4)18(23)24-10-20-16(21)12-7-5-6-8-13(12)17(20)22/h9,14-15H,5-8,10H2,1-4H3

InChI Key

CXBMCYHAMVGWJQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Bicyclic monoterpenoid
Isoindolone
Monoterpenoid
Isoindole
Maleimide
Cyclopropanecarboxylic acid or derivatives
Carboxylic acid imide, n-substituted
Pyrroline
Carboxylic acid imide
Dicarboximide
Carboxylic acid ester
Lactam
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cyclopropanes (CHEBI:39397 )
phthalimide insecticide (CHEBI:39397 )
Pyrethroid insecticides (C18373 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

pyrethroid ester insecticide

Biological Roles

pyrethroid ester insecticide ?

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

The racemic isomer is a colourless crystalline solid. The (1R)-isomer is a yellow or brown viscous liquid (6).

Experimental Properties

Property	Value
Melting Point	69°C
Boiling Point	Not Available
Solubility	0.00183 mg/mL at 25°C [TOMLIN,C (1997)]

Predicted Properties

Property	Value	Source
Water Solubility	0.075 g/L	ALOGPS
logP	2.84	ALOGPS
logP	3.09	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.19 m³·mol⁻¹	ChemAxon
Polarizability	36.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0w30-0914000000-8d0f8879961828dc6abf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ik9-1900000000-962d8c4288f0e1b2d7b8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zgi-9600000000-3a0666ffcfaf453348bf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fai-0904000000-2534905791b09dd44487	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-1901000000-81333aa37d4f7eae1da0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pk9-2900000000-a348ae4a06d6c20ce637	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
5000.0 mg/kg	Rat	LD50	Oral	experimental	Not Available	6
2205.0 Log mg/kg [1200:3900]	Rat	LD50	oral	predicted	Not Available	Not Available
72.0 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
0.1 mg/kg-day	Rat	NOEL	injection	experimental	Not Available	ECOTOX - EPA ORD
0.3 mg/kg-day	Rat	LOEL	injection	experimental	Not Available	ECOTOX - EPA ORD
5.0 mg/kg-day	Rat	LOEL	injection	experimental	Not Available	ECOTOX - EPA ORD
100.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
5.0 mg/kg-day	Rat	LOEL	injection	experimental	Not Available	ECOTOX - EPA ORD
5.0 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
800.0 mg/kg-day	Rat	NOEL	injection	experimental	Not Available	ECOTOX - EPA ORD
800.0 mg/kg-day	Rat	NOEL	injection	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. (7, 8, 5) LD50 (racemate isomer): 2000 mg/kg (Oral, Mouse) (6) LD50 (1R-isomer): 1060 mg/kg (Oral, Mouse) (6)

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

Not Available

Symptoms

Following oral exposure, severe fine tremor, marked reflex hyperexcitability, sympathetic activation can occur. Nausea, vomiting and abdominal pain commonly occur and develop following ingestion. Sudden bronchospasm, swelling of oral and laryngeal mucous membranes, and anaphylactoid reactions have been reported after inhalation. Hypersensitivity reactions characterized by pneumonitis, cough, dyspnea, wheezing, chest pain, irritability to sound and touch, and bronchospasm may occur too . Dermatitis is the main effect of a dermal exposure to tetramethrin. (9)

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
CEDs000010	Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.	Agriculture & land management	PubChem
CEDs000019	Indoor air?Indoor air can be a significant reservoir for synthetic chemical contaminants, which often originate from various sources within enclosed environments.	Air, dust & atmospheric transport	Not Available
CEDs000070	Stormwater runoff?Stormwater runoff refers to the flow of rainwater or melted snow that does not soak into the ground and instead collects pollutants as it travels over impervious surfaces such as roads and parking lots.	Automotive & urban infrastructure	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
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
CEDs000505	Amplifiers?Amplifiers, commonly used in various electronic devices to enhance signal strength, can be a source of synthetic chemical contamination due to the materials and processes involved in their production and disposal.	Electrical & Electronic Equipment	PubChem
CEDs000508	Coils?Coils are components used in various electrical and electronic applications, such as transformers, inductors, and motors.	Electrical & Electronic Equipment	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
CEDs000517	Electric Switches?Electric switches, integral components in numerous devices, can be a source of synthetic chemical contamination due to the materials and manufacturing processes involved in their production.	Electrical & Electronic Equipment	PubChem
CEDs000519	Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.	Electrical & Electronic Equipment	PubChem
CEDs000524	Hybrid Capacitors?Hybrid capacitors are energy storage devices that combine the properties of electrolytic and supercapacitors, utilizing a combination of electrochemical principles to achieve higher energy density and power density.	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
CEDs000547	Preparation Of Malt?Malt preparation involves the germination and drying of cereal grains, primarily barley, to produce malt for brewing and 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
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	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
CEDs000583	Anchoring Equipment?Anchoring equipment, commonly used in marine applications, can be a source of synthetic chemical contamination due to the materials and coatings utilized in their manufacturing.	Marine, shipping & aquaculture	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
CEDs000597	Chemosterilants?Chemosterilants are synthetic chemicals designed to induce sterility in target pest populations, thereby controlling their reproduction and mitigating damage to crops.	Agriculture & land management	PubChem
CEDs000598	Fertiliser Distributors?Fertiliser distributors play a critical role in the supply of synthetic fertilizers, which are widely used to enhance soil fertility and crop yield.	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
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000634	Buckles?Buckles, commonly used as fasteners in clothing, accessories, and furniture, can be a source of synthetic chemical contamination due to the materials and coatings employed in their production.	Textiles, leather & furnishings	PubChem
CEDs000661	Umbrellas?Umbrellas are commonly manufactured using synthetic materials such as polyester, nylon, and polyvinyl chloride (PVC), which can contribute to synthetic chemical contamination.	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
CEDs000667	Gaseous Fire Fighting?Gaseous fire fighting systems utilize synthetic chemicals, such as halocarbons and inert gases, to suppress fires through chemical and physical processes.	Fire suppression systems & agents	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
CEDs000686	Clay Wares?Clay wares are ceramic products made from natural clay, often utilized in various construction applications such as tiles, bricks, and sanitary ware.	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
CEDs000698	Jewellery?Jewellery production often involves the use of various synthetic chemicals during the extraction and processing of metals.	Mining & metal processing	PubChem
CEDs000734	Coating Compositions?Coating compositions, which include paints, sealants, and varnishes, are formulated with a variety of synthetic chemicals such as solvents, resins, pigments, and additives.	Building & Construction	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
CEDs00923	Complete Feed	Agriculture & land management	PMC13011801
CEDs01279	Vegetable Samples	Food, food processing & cookware	PMC7363064
CEDs01601	Fresh Fruits	Food, food processing & cookware	PMC7363064

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	17-beta-hydroxysteroid-dehydrogenase	O93874	Cochliobolus lunatus	Predicted (SEA)	Prediction Confidence Score 0.25 Applicability Domain 0.25 Low confidence Statistical Significance 0.003 Supporting Reference Compounds 1 E-value 23.5105
Click to view 3D structure	Protoporphyrinogen oxidase, chloroplastic	Q9AR38	Oryza sativa subsp. japonica	Predicted (SEA)	Prediction Confidence Score 0.21 Applicability Domain 0.222 Low confidence Statistical Significance 4.70e-04 Supporting Reference Compounds 2 E-value 3.65891
Click to view 3D structure	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 4	Q9Y237	Humans	Predicted (SEA)	Prediction Confidence Score 0.207 Applicability Domain 0.207 Low confidence Statistical Significance 0.0086 Supporting Reference Compounds 1 E-value 67.0282
Click to view 3D structure	Pyruvate carboxylase	A0A0H3JRU9	Staphylococcus aureus (strain Mu50 / ATCC 700699)	Predicted (SEA)	Prediction Confidence Score 0.206 Applicability Domain 0.206 Low confidence Statistical Significance 0.0184 Supporting Reference Compounds 1 E-value 143.009
Click to view 3D structure	Beta-lactamase	P00807	Staphylococcus aureus	Predicted (SEA)	Prediction Confidence Score 0.205 Applicability Domain 0.246 Low confidence Statistical Significance 3.70e-04 Supporting Reference Compounds 10 E-value 2.88042
Click to view 3D structure	Beta-lactamase TEM	P62593	Escherichia coli	Predicted (SEA)	Prediction Confidence Score 0.203 Applicability Domain 0.215 Low confidence Statistical Significance 6.40e-04 Supporting Reference Compounds 22 E-value 4.98235
Click to view 3D structure	Beta-lactamase	P05364	Enterobacter cloacae	Predicted (SEA)	Prediction Confidence Score 0.201 Applicability Domain 0.215 Low confidence Statistical Significance 7.70e-04 Supporting Reference Compounds 22 E-value 5.99439
Click to view 3D structure	Coproporphyrinogen III oxidase	P32397	Bacillus subtilis (strain 168)	Predicted (SEA)	Prediction Confidence Score 0.2 Applicability Domain 0.2 Low confidence Statistical Significance 0.0334 Supporting Reference Compounds 1 E-value 260.094
Click to view 3D structure	Solute carrier family 12 member 5	Q63633	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.191 Applicability Domain 0.191 Low confidence Statistical Significance 0.0546 Supporting Reference Compounds 1 E-value 424.745
Click to view 3D structure	Adenylate cyclase type 1	P19754	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.19 Applicability Domain 0.213 Low confidence Statistical Significance 7.70e-04 Supporting Reference Compounds 5 E-value 5.99439
Click to view 3D structure	Beta-lactamase OXA-2	P0A1V9	Escherichia coli	Predicted (SEA)	Prediction Confidence Score 0.188 Applicability Domain 0.188 Low confidence Statistical Significance 2.30e-04 Supporting Reference Compounds 1 E-value 1.79053
Click to view 3D structure	Beta-lactamase pse-1	Q2V0Y6	Escherichia coli	Predicted (SEA)	Prediction Confidence Score 0.188 Applicability Domain 0.188 Low confidence Statistical Significance 2.30e-04 Supporting Reference Compounds 1 E-value 1.79053
Click to view 3D structure	Replicase polyprotein 1ab	P0DTD1	SARS-CoV-2	Predicted (SEA)	Prediction Confidence Score 0.187 Applicability Domain 0.25 Low confidence Statistical Significance 0.5952 Supporting Reference Compounds 215 E-value 4633.74
Click to view 3D structure	Arylamine N-acetyltransferase	O86309	Mycolicibacterium smegmatis	Predicted (SEA)	Prediction Confidence Score 0.187 Applicability Domain 0.187 Low confidence Statistical Significance 0.0348 Supporting Reference Compounds 1 E-value 270.837
Click to view 3D structure	Extended-spectrum beta-lactamase PER-6	D5HSX5	Aeromonas allosaccharophila	Predicted (SEA)	Prediction Confidence Score 0.186 Applicability Domain 0.186 Low confidence Statistical Significance 8.50e-04 Supporting Reference Compounds 1 E-value 6.61718
Click to view 3D structure	ADC-14 protein	Q0VTR6	Acinetobacter genomosp. 3	Predicted (SEA)	Prediction Confidence Score 0.186 Applicability Domain 0.186 Low confidence Statistical Significance 8.50e-04 Supporting Reference Compounds 1 E-value 6.61718
Click to view 3D structure	Beta-lactamase SHV-11	Q7X575	Escherichia coli	Predicted (SEA)	Prediction Confidence Score 0.186 Applicability Domain 0.186 Low confidence Statistical Significance 8.50e-04 Supporting Reference Compounds 1 E-value 6.61718
Click to view 3D structure	ADC-16 protein	Q0VTR8	Acinetobacter genomosp. 3	Predicted (SEA)	Prediction Confidence Score 0.186 Applicability Domain 0.186 Low confidence Statistical Significance 8.50e-04 Supporting Reference Compounds 1 E-value 6.61718
Click to view 3D structure	Solute carrier family 2, facilitated glucose transporter member 1	P11166	Humans	Predicted (SEA)	Prediction Confidence Score 0.186 Applicability Domain 0.213 Low confidence Statistical Significance 0.516 Supporting Reference Compounds 62 E-value 4017.25
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	Prediction Confidence Score 0.185 Applicability Domain 0.195 Low confidence Statistical Significance 0.5119 Supporting Reference Compounds 119 E-value 3984.95
Click to view 3D structure	Beta-lactamase	P00808	Bacillus licheniformis	Predicted (SEA)	Prediction Confidence Score 0.184 Applicability Domain 0.217 Low confidence Statistical Significance 3.80e-04 Supporting Reference Compounds 6 E-value 2.95827
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.195 Low confidence Statistical Significance 0.55 Supporting Reference Compounds 154 E-value 4281.86
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.195 Low confidence Statistical Significance 0.6179 Supporting Reference Compounds 201 E-value 4810.61
Click to view 3D structure	Beta-lactamase	P05193	Citrobacter freundii	Predicted (SEA)	Prediction Confidence Score 0.182 Applicability Domain 0.217 Low confidence Statistical Significance 2.90e-04 Supporting Reference Compounds 6 E-value 2.25763
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	Prediction Confidence Score 0.182 Applicability Domain 0.195 Low confidence Statistical Significance 0.3715 Supporting Reference Compounds 74 E-value 2891.79
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	Matrix metalloproteinase-9	P14780	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Known	Not Available
Click to view 3D structure	C-C motif chemokine 2	P13500	Humans	Known	Not Available
Click to view 3D structure	E-selectin	P16581	Humans	Known	Not Available
Click to view 3D structure	Prostaglandin E2 receptor EP2 subtype	P43116	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Known	Not Available
Click to view 3D structure	Hepatocyte nuclear factor 4-alpha	P41235	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 2C19	P33261	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB13752

HMDB ID

HMDB0258915

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

Tetramethrin

Chemspider ID

75773

ChEBI ID

39397

PubChem Compound ID

Not Available

Kegg Compound ID

C18373

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. doi: 10.1124/dmd.108.022343. Epub 2008 Oct 23. [PubMed: 18948380]
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]
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
International Programme on Chemical Safety (IPCS) INCHEM (1989). Health and Safety Guide forTetramethrin. - http://www.inchem.org/documents/hsg/hsg/hsg031.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.

Tetramethrin (CED0010011)

Structure for CHEM000886: Tetramethrin

No pathways found

Structure