TETRAMETHRIN

Details

Stereochemistry	MIXED
Molecular Formula	C19H25NO4
Molecular Weight	331.4061
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=CXBMCYHAMVGWJQ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.pestfix.co.uk/Tetramethrin.asp | https://www.ncbi.nlm.nih.gov/pubmed/28099443 | http://www.toxipedia.org/display/toxipedia/Tetramethrin

Tetramethrin is a synthetic pyrethroid based on the natural counterpart found in chrysanthemum flowers but more stable and longer lasting. Amongst one of the most widely used insecticides, Tetramethrin is a fast acting neurotoxin used against most flying and crawling insects. It is often used in combination with other active ingredients to create a multi-action pesticide. Tetramethrin was found to inhibit various ABC and SLC drug transporters, including multidrug resistance-associated protein(MRP) 2, breast cancer resistance protein (BCRP), organic anion transporter polypeptide (OATP) 1B1, organic anion transporter (OAT) 3, multidrug and toxin extrusion transporter (MATE) 1, organic cation transporter (OCT) 1 and OCT2.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
ATP-binding cassette sub-family G member 2 16 Target ID: CHEMBL5393 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8504	72.5 µM [IC50]
Canalicular multispecific organic anion transporter 1 21 Target ID: CHEMBL5748 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8504	65.5 µM [IC50]
Solute carrier organic anion transporter family member 1B1 32 Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8504	5.7 µM [IC50]
Solute carrier family 22 member 8 17 Target ID: CHEMBL1641348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8504	77.6 µM [IC50]
Solute carrier family 22 member 1 18 Target ID: CHEMBL5685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8504	4.9 µM [IC50]
Solute carrier family 22 member 2 8 Target ID: CHEMBL1743122 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8504	11.2 µM [IC50]
sodium channel activity 16 Target ID: GO:0005272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8613953 \| https://www.ncbi.nlm.nih.gov/pubmed/8814900	Modulator 846

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Glucocorticoid-like activity of propylparaben, butylparaben, diethylhexyl phthalate and tetramethrin mixtures studied in the MDA-kb2 cell line.	2015-01-22	25448277
Molecular docking revealed potential disruptors of glucocorticoid receptor-dependent reporter gene expression.	2014-04-21	24518828
Environmental impact on vascular development predicted by high-throughput screening.	2011-11	21788198
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.	2011-09-14	21786822
Simultaneous determination of 16 pyrethroid residues in tea samples using gas chromatography and ion trap mass spectrometry.	2010-10	20875241
Assessing hormone receptor activities of pyrethroid insecticides and their metabolites in reporter gene assays.	2010-07	20410157
Malignant mammary tumor in female dogs: environmental contaminants.	2010-06-30	20587072
Triatoma infestans bugs in Southern Patagonia, Argentina.	2010-05	20409398
A rapid and sensitive analytical method for the determination of 14 pyrethroids in water samples.	2010-04-09	20206936
Repeated-dose 14-day dermal toxicity of different combinations of some synthetic pyrethroid insecticides, piperonyl butoxide, and tetramethrin in rats.	2010-03	19947829
Simultaneous determination of nine pyrethroids in indoor insecticide products by capillary gas chromatography.	2010-02-05	19875265
Consumer exposure to biocides--identification of relevant sources and evaluation of possible health effects.	2010-02-03	20128903
Acute toxicity to zebrafish of two organophosphates and four pyrethroids and their binary mixtures.	2010-01	19728319
Parkinson's disease: is it a toxic syndrome?	2010	21152209
Level of CYP4G19 Expression Is Associated with Pyrethroid Resistance in Blattella germanica.	2010	20700426
Irritability and repellency of synthetic pyrethroids on an Aedes aegypti population from Thailand.	2009-12	20836825
Evidence for dose-additive effects of pyrethroids on motor activity in rats.	2009-10	20019907
Use of biocidal products (insect sprays and electro-vaporizer) in indoor areas--exposure scenarios and exposure modeling.	2009-09	19345645
Simultaneous determination of 18 pyrethroids in indoor air by gas chromatography/mass spectrometry.	2009-06-26	19457492
Pyrethroid insecticides: isoform-dependent hydrolysis, induction of cytochrome P450 3A4 and evidence on the involvement of the pregnane X receptor.	2009-05-15	19249324
Household exposure to pesticides and bladder exstrophy in a newborn baby boy: a case report and review of the literature.	2009-03-30	19830118
Behavioral-based educational intervention directed toward Egyptian agricultural families to protect children from pesticide exposure.	2009-01-10	19131303
Dynamics of esterase alleles in Culex pipiens complex mosquitoes in Beijing.	2008-12	19133472
Transcriptional response of rat frontal cortex following acute in vivo exposure to the pyrethroid insecticides permethrin and deltamethrin.	2008-11-18	19017407
Direct chiral resolution and its application to the determination of the pesticide tetramethrin in soil by high-performance liquid chromatography using polysaccharide-type chiral stationary phase.	2008-10	19007479
Anopheles gambiae complex along The Gambia river, with particular reference to the molecular forms of An. gambiae s.s.	2008-09-22	18803885
Developmentally-regulated sodium channel subunits are differentially sensitive to alpha-cyano containing pyrethroids.	2008-09-15	18538810
Dry season ecology of Anopheles gambiae complex mosquitoes in The Gambia.	2008-08-18	18710559
Impact of urban agriculture on malaria vectors in Accra, Ghana.	2008-08-04	18680565
Acute toxicity of organophosphorus and pyrethroid insecticides to Bombyx mori.	2008-04	18459399
Orthogonal signal correction-partial least squares method for simultaneous spectrophotometric determination of cypermethrin and tetramethrin.	2008-04	17652014
Household vacuum cleaners vs. the high-volume surface sampler for collection of carpet dust samples in epidemiologic studies of children.	2008-02-21	18291036
Pyrethroids as promising marine antifoulants: laboratory and field studies.	2008-01-05	18654821
Effects of insecticides on the fluidity of mitochondrial membranes of the diamondback moth, Plutella xylostella, resistant and susceptible to avermectin.	2008	20345311
Monitoring lymphatic filariasis interventions: Adult mosquito sampling, and improved PCR - based pool screening method for Wuchereria bancrofti infection in Anopheles mosquitoes.	2007-11-29	18047647
Differential response of Mono Mac 6, BEAS-2B, and Jurkat cells to indoor dust.	2007-09	17805423
Differential pharmacology of the cardiac anionic background current I(AB).	2007-08-27	17603033
"Sexual" population structure and genetics of the malaria agent P. falciparum.	2007-07-18	17637829
Comparison of two partial least squares infrared spectrometric methods for the quality control of pediculosis lotions.	2007-01-16	17386490
Identification and quantitation of pyrethroid pesticide residues in vegetables by solid-phase extraction and liquid chromatography/electrospray ionization ion trap mass spectrometry.	2007	17510928
Comparison of prostate cancer cell lines for androgen receptor-mediated reporter gene assays.	2006-10	16621434
Reinfestation sources for Chagas disease vector, Triatoma infestans, Argentina.	2006-07	16836826
Biomarker of pyrethrum exposure.	2006-04-10	16257148
Toxicity of pyrethroids and repellency of diethyltoluamide in two deltamethrin-resistant colonies of Triatoma infestans Klug, 1834 (Hemiptera: Reduviidae).	2006-02	16699715
Comparison of different mass spectrometric detection techniques in the gas chromatographic analysis of pyrethroid insecticide residues in soil after microwave-assisted extraction.	2006-02	16362291
Distribution of pesticide residues within homes in central New York State.	2006-01	16237496
Assessment of estrogenic and androgenic activities of tetramethrin in vitro and in vivo assays.	2005-12-10	16326440
[Calcium influx: an intracellular message of the mitogenic action of insulin-like growth factors].	1989-03	2539779
Calcium influx: an intracellular message of the mitogenic action of insulin-like growth factor-I.	1988-11-15	2460452
Insulin-like growth factor II stimulates calcium influx in competent BALB/c 3T3 cells primed with epidermal growth factor. Characteristics of calcium influx and involvement of GTP-binding protein.	1987-09-05	2442157

Patents

Sample Use Guides

In Vivo Use Guide

Rats: In the uterotrophic assay using 18-d-old female Sprague-Dawley rats, subcutaneous treatment with tetramethrin (5 to 800 mg/kg/day) for 3 d led to a statistically significant decrease in absolute and relative uterine wet weights at all doses tested. Moreover, tetramethrin blocked the effect of E2 on uterine weights.

Route of Administration: Other

In Vitro Use Guide

In electrically-stimulated longitudinal muscle-myenteric plexus preparations of the guinea-pig ileum, tetramethrin (1-100 uM) caused a biphasic response consisting of an early transient increase followed by a sustained decrease in the amplitude of cholinergic contractions.

Name

Type

Language

TETRAMETHRIN

Official Name

English

1-cyclohexene-1,2-dicarboximidomethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Preferred Name

English

TETRAMETHRIN [ISO]

Common Name

English

TETRAMETHRIN [MI]

Common Name

English

CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPEN-1-YL)-, (1,3,4,5,6,7-HEXAHYDRO-1,3-DIOXO-2H-ISOINDOL-2-YL)METHYL ESTER

Common Name

English

TETRAMETHRIN [HSDB]

Common Name

English

TETRAMETHRIN [MART.]

Common Name

English

2,2-DIMETHYL-3-(2-METHYLPROPENYL)CYCLOPROPANECARBOXYLIC ACID, ESTER WITH N-(HYDROXYMETHYL)-1-CYCLOHEXENE-1,2-DICARBOXIMIDE

Common Name

English

tetramethrin [INN]

Common Name

English

Tetramethrin [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QP53AC13