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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 of TETRAMETHRIN

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

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

Kato, T. et al.
1
Curator's Comment: Tetramethrin was first synthesized in 1964 by Kato et al.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 72.5 µM [IC50]
Inhibitor
8297
 65.5 µM [IC50]
Inhibitor
8297
 5.7 µM [IC50]
Inhibitor
8297
 77.6 µM [IC50]
Inhibitor
8297
 4.9 µM [IC50]
Inhibitor
8297
 11.2 µM [IC50]
Modulator
828
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
[Calcium influx: an intracellular message of the mitogenic action of insulin-like growth factors].
1989 Mar
Oscillation of cytoplasmic free calcium concentration induced by insulin-like growth factor I.
1992 Mar
Kinetics of modulation of tetrodotoxin-sensitive and tetrodotoxin-resistant sodium channels by tetramethrin and deltamethrin.
2001 Dec
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
Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection.
2003 Nov-Dec
Microelectrode array recordings of cardiac action potentials as a high throughput method to evaluate pesticide toxicity.
2006 Apr
Toxicity of pyrethroids and repellency of diethyltoluamide in two deltamethrin-resistant colonies of Triatoma infestans Klug, 1834 (Hemiptera: Reduviidae).
2006 Feb
Comparison of different mass spectrometric detection techniques in the gas chromatographic analysis of pyrethroid insecticide residues in soil after microwave-assisted extraction.
2006 Feb
Identification and quantitation of pyrethroid pesticide residues in vegetables by solid-phase extraction and liquid chromatography/electrospray ionization ion trap mass spectrometry.
2007
Differential pharmacology of the cardiac anionic background current I(AB).
2007 Aug 27
"Sexual" population structure and genetics of the malaria agent P. falciparum.
2007 Jul 18
Behavioral-based educational intervention directed toward Egyptian agricultural families to protect children from pesticide exposure.
2007-2008
Orthogonal signal correction-partial least squares method for simultaneous spectrophotometric determination of cypermethrin and tetramethrin.
2008 Apr
Impact of urban agriculture on malaria vectors in Accra, Ghana.
2008 Aug 4
Dynamics of esterase alleles in Culex pipiens complex mosquitoes in Beijing.
2008 Dec
Household vacuum cleaners vs. the high-volume surface sampler for collection of carpet dust samples in epidemiologic studies of children.
2008 Feb 21
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
Developmentally-regulated sodium channel subunits are differentially sensitive to alpha-cyano containing pyrethroids.
2008 Sep 15
Simultaneous determination of 18 pyrethroids in indoor air by gas chromatography/mass spectrometry.
2009 Jun 26
Evidence for dose-additive effects of pyrethroids on motor activity in rats.
2009 Oct
Use of biocidal products (insect sprays and electro-vaporizer) in indoor areas--exposure scenarios and exposure modeling.
2009 Sep
Simultaneous determination of nine pyrethroids in indoor insecticide products by capillary gas chromatography.
2010 Feb 5
Acute toxicity to zebrafish of two organophosphates and four pyrethroids and their binary mixtures.
2010 Jan
Assessing hormone receptor activities of pyrethroid insecticides and their metabolites in reporter gene assays.
2010 Jul
Repeated-dose 14-day dermal toxicity of different combinations of some synthetic pyrethroid insecticides, piperonyl butoxide, and tetramethrin in rats.
2010 Mar
Triatoma infestans bugs in Southern Patagonia, Argentina.
2010 May
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.
2011 Sep 14
Glucocorticoid-like activity of propylparaben, butylparaben, diethylhexyl phthalate and tetramethrin mixtures studied in the MDA-kb2 cell line.
2015 Jan 22
Patents

Patents

JP2001002513A
1
JP2001163712A
1
JP2007518737A
11
JP2011526599A
45
JPH0327301A
3
JPS59110603A
2

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Tetramethrin is practically non-toxic to birds and mammals. The LD50 in rats exceeded the testing limit of 5000 mg/kg for tests in both ingestion and dermal absorption (#EPA). In a WHO study, Male Wistar rats here given a dose of 500 mg/kg, of which 95% was metabolized and excreted within five days, indicating that tetramethrin is absorbed and secreted relatively quickly. http://www.toxipedia.org/display/toxipedia/Tetramethrin
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 GMT 2023
Edited
by admin
on Sat Dec 16 17:44:59 GMT 2023
Record UNII
Z72930Q46K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TETRAMETHRIN
HSDB   INCI   INN   ISO   MART.   MI   WHO-DD  
INN   INCI  
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
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
EPA PESTICIDE CODE 69003
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
NCI_THESAURUS C737
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
WHO-ATC P03BA04
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
Code System Code Type Description
MESH
C009424
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
WIKIPEDIA
TETRAMETHRIN
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
ECHA (EC/EINECS)
231-711-6
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
SMS_ID
100000082737
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
DRUG BANK
DB13752
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
MERCK INDEX
m10640
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY Merck Index
CAS
7696-12-0
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
ALANWOOD
tetramethrin
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
DRUG CENTRAL
4730
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
PUBCHEM
83975
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
INN
5509
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL1788386
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID6032649
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
NCI_THESAURUS
C80607
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
HSDB
6738
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
FDA UNII
Z72930Q46K
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
EVMPD
SUB10944MIG
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
PRIMARY
Related Record Type Details
Structure of TETRAMETHRIN
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