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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

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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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
72.5 µM [IC50]
65.5 µM [IC50]
5.7 µM [IC50]
77.6 µM [IC50]
4.9 µM [IC50]
11.2 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

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.