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

Molecular Formula	C19H25NO4
Molecular Weight	331.4061
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 8297	72.5 µM [IC50]
Canalicular multispecific organic anion transporter 1 21 Target ID: CHEMBL5748 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8297	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 8297	5.7 µM [IC50]
Solute carrier family 22 member 8 17 Target ID: CHEMBL1641348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8297	77.6 µM [IC50]
Solute carrier family 22 member 1 18 Target ID: CHEMBL5685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8297	4.9 µM [IC50]
Solute carrier family 22 member 2 8 Target ID: CHEMBL1743122 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8297	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 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
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 Sep 5	2442157
Calcium influx: an intracellular message of the mitogenic action of insulin-like growth factor-I.	1988 Nov 15	2460452
[Calcium influx: an intracellular message of the mitogenic action of insulin-like growth factors].	1989 Mar	2539779
Oscillation of cytoplasmic free calcium concentration induced by insulin-like growth factor I.	1992 Mar	1550224
Indoor thermal fogging application of pesguard FG 161, a mixture of d-tetramethrin and cyphenothrin, using portable sprayer against vector mosquitoes in the tropical environment.	2001 Mar	11345415
Characterisation of gene expression patterns in 22RV1 cells for determination of environmental androgenic/antiandrogenic compounds.	2003 Feb	12711008
Simultaneous determination of pyrethroid and pyrethrin metabolites in human urine by gas chromatography-high resolution mass spectrometry.	2005 Jan 25	15639450
Microelectrode array recordings of cardiac action potentials as a high throughput method to evaluate pesticide toxicity.	2006 Apr	16198528
Biomarker of pyrethrum exposure.	2006 Apr 10	16257148
Toxicity of pyrethroids and repellency of diethyltoluamide in two deltamethrin-resistant colonies of Triatoma infestans Klug, 1834 (Hemiptera: Reduviidae).	2006 Feb	16699715
Distribution of pesticide residues within homes in central New York State.	2006 Jan	16237496
Reinfestation sources for Chagas disease vector, Triatoma infestans, Argentina.	2006 Jul	16836826
Comparison of prostate cancer cell lines for androgen receptor-mediated reporter gene assays.	2006 Oct	16621434
Identification and quantitation of pyrethroid pesticide residues in vegetables by solid-phase extraction and liquid chromatography/electrospray ionization ion trap mass spectrometry.	2007	17510928
Differential pharmacology of the cardiac anionic background current I(AB).	2007 Aug 27	17603033
Monitoring lymphatic filariasis interventions: Adult mosquito sampling, and improved PCR - based pool screening method for Wuchereria bancrofti infection in Anopheles mosquitoes.	2007 Nov 29	18047647
Effects of insecticides on the fluidity of mitochondrial membranes of the diamondback moth, Plutella xylostella, resistant and susceptible to avermectin.	2008	20345311
Orthogonal signal correction-partial least squares method for simultaneous spectrophotometric determination of cypermethrin and tetramethrin.	2008 Apr	17652014
Dry season ecology of Anopheles gambiae complex mosquitoes in The Gambia.	2008 Aug 18	18710559
Impact of urban agriculture on malaria vectors in Accra, Ghana.	2008 Aug 4	18680565
Household vacuum cleaners vs. the high-volume surface sampler for collection of carpet dust samples in epidemiologic studies of children.	2008 Feb 21	18291036
Transcriptional response of rat frontal cortex following acute in vivo exposure to the pyrethroid insecticides permethrin and deltamethrin.	2008 Nov 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 Oct	19007479
Developmentally-regulated sodium channel subunits are differentially sensitive to alpha-cyano containing pyrethroids.	2008 Sep 15	18538810
Irritability and repellency of synthetic pyrethroids on an Aedes aegypti population from Thailand.	2009 Dec	20836825
Simultaneous determination of 18 pyrethroids in indoor air by gas chromatography/mass spectrometry.	2009 Jun 26	19457492
Household exposure to pesticides and bladder exstrophy in a newborn baby boy: a case report and review of the literature.	2009 Mar 30	19830118
Pyrethroids as promising marine antifoulants: laboratory and field studies.	2009 Mar-Apr	18654821
Pyrethroid insecticides: isoform-dependent hydrolysis, induction of cytochrome P450 3A4 and evidence on the involvement of the pregnane X receptor.	2009 May 15	19249324
Evidence for dose-additive effects of pyrethroids on motor activity in rats.	2009 Oct	20019907
Use of biocidal products (insect sprays and electro-vaporizer) in indoor areas--exposure scenarios and exposure modeling.	2009 Sep	19345645
Parkinson's disease: is it a toxic syndrome?	2010	21152209
Level of CYP4G19 Expression Is Associated with Pyrethroid Resistance in Blattella germanica.	2010	20700426
A rapid and sensitive analytical method for the determination of 14 pyrethroids in water samples.	2010 Apr 9	20206936
Consumer exposure to biocides--identification of relevant sources and evaluation of possible health effects.	2010 Feb 3	20128903
Simultaneous determination of nine pyrethroids in indoor insecticide products by capillary gas chromatography.	2010 Feb 5	19875265
Acute toxicity to zebrafish of two organophosphates and four pyrethroids and their binary mixtures.	2010 Jan	19728319
Assessing hormone receptor activities of pyrethroid insecticides and their metabolites in reporter gene assays.	2010 Jul	20410157
Malignant mammary tumor in female dogs: environmental contaminants.	2010 Jun 30	20587072
Repeated-dose 14-day dermal toxicity of different combinations of some synthetic pyrethroid insecticides, piperonyl butoxide, and tetramethrin in rats.	2010 Mar	19947829
Triatoma infestans bugs in Southern Patagonia, Argentina.	2010 May	20409398
Simultaneous determination of 16 pyrethroid residues in tea samples using gas chromatography and ion trap mass spectrometry.	2010 Oct	20875241
Environmental impact on vascular development predicted by high-throughput screening.	2011 Nov	21788198
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.	2011 Sep 14	21786822
Molecular docking revealed potential disruptors of glucocorticoid receptor-dependent reporter gene expression.	2014 Apr 21	24518828
Glucocorticoid-like activity of propylparaben, butylparaben, diethylhexyl phthalate and tetramethrin mixtures studied in the MDA-kb2 cell line.	2015 Jan 22	25448277

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:44:59 UTC 2023` Edited by `admin` on `Sat Dec 16 17:44:59 UTC 2023`
Record UNII	Z72930Q46K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRAMETHRIN

Official 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

TETRAMETHRIN [INCI]

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

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

Common Name

English

Classification Tree Code System Code

WHO-VATC

QP53AC13