U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C22H26O3
Molecular Weight 338.44
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RESMETHRIN, TRANS-(±)-

SMILES

CC(C)=C[C@@H]1[C@@H](C(=O)OCC2=COC(CC3=CC=CC=C3)=C2)C1(C)C

InChI

InChIKey=VEMKTZHHVJILDY-UXHICEINSA-N
InChI=1S/C22H26O3/c1-15(2)10-19-20(22(19,3)4)21(23)25-14-17-12-18(24-13-17)11-16-8-6-5-7-9-16/h5-10,12-13,19-20H,11,14H2,1-4H3/t19-,20+/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H26O3
Molecular Weight 338.44
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Bioresmethrin is a synthetic pyrethroid insecticide. It is the (+)-trans isomer of resmethrin which itself contains a minimum of 30% bioresmethrin. Bioresmethrin is the [1R, trans] isomer of resmethrin and has greater insecticidal activity than the racemic mixture. Bioresmethrin is a potent contact insecticide effective against a wide range of household insects, plant pests, grain pests and insects found in animal housing. It exhibits a high order of insecticidal activity, which when coupled with its excellent toxicological properties, makes it potentially one of the safest and most useful insecticides now being produced.

CNS Activity

Curator's Comment: As for every type I pyrethroid, bioresmethrin effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli.

Originator

Curator's Comment: Bioresmethrin was discovered in England by M. Elliott and co-workers at the Rothamsted Experimental Station in collaboration with the National Research and Development Corporation (NRDC).

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids.
2010-01
Evidence for dose-additive effects of pyrethroids on motor activity in rats.
2009-10
Pyrethroid insecticides: isoform-dependent hydrolysis, induction of cytochrome P450 3A4 and evidence on the involvement of the pregnane X receptor.
2009-05-15
In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms.
2009-01
Impact of urban agriculture on malaria vectors in Accra, Ghana.
2008-08-04
Susceptibility to thiamethoxam of Musca domestica from Danish livestock farms.
2008-02
Hydrolysis of pyrethroids by human and rat tissues: examination of intestinal, liver and serum carboxylesterases.
2007-05-15
Human carboxylesterases and their role in xenobiotic and endobiotic metabolism.
2007
Identification and quantitation of pyrethroid pesticide residues in vegetables by solid-phase extraction and liquid chromatography/electrospray ionization ion trap mass spectrometry.
2007
Hydrolytic metabolism of pyrethroids by human and other mammalian carboxylesterases.
2006-02-28
Glutathione S-transferase and insecticide resistance in laboratory strains and field populations of Musca domestica.
2005-08
Structure-activity and interaction effects of 14 different pyrethroids on voltage-gated chloride ion channels.
2004-02
Pyrethroid stimulation of ion transport across frog skin.
2003-06
Synergized bifenthrin plus chlorpyrifos-methyl for control of beetles and psocids in sorghum in Australia.
2003-04
Long-term effectiveness of grain protectants and structural treatments against Liposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of stored products.
2002-12
Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin.
2002-09-25
Field studies on the susceptibility of housefly to certain insecticides in nine Egyptian governorates.
2002-04
Enhanced efficiency of electrostatically charged insecticide aerosols.
2001-05
The status and development of insecticide resistance in Danish populations of the housefly Musca domestica L.
2001-01
Patents

Patents

Sample Use Guides

2 groups each of 3 rats received i.v. injections into the lateral tail vein of 2.5 mg/kg ([U-14C]phenyl, 2uCi/rat) cismethrin or bioresmethrin as a solution in glycerin formal (3.75 mg/ml).
Route of Administration: Intravenous
In Vitro Use Guide
Glial cells in the ganglia and ventral connectives of Periplaneta americana treated with 5 uM bioresmethrin were found to be swollen and even more electron lucent than the control cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:00:31 GMT 2025
Edited
by admin
on Mon Mar 31 21:00:31 GMT 2025
Record UNII
8535H601Y7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RESMETHRIN, TRANS-(±)-
Common Name English
3-FURANMETHANOL, 5-BENZYL-, 2,2-DIMETHYL-3-(2-METHYLPROPENYL)CYCLOPROPANECARBOXYLATE, TRANS-(±)-
Preferred Name English
CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)-, (5-(PHENYLMETHYL)-3-FURANYL)METHYL ESTER, (1R,3R)-REL-
Common Name English
TRANS-(5-BENZYL-3-FURYL)METHYL 2,2-DIMETHYL-3-(2-METHYLPROPENYL)CYCLOPROPANECARBOXYLATE
Common Name English
CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYLPROPENYL)-, (5-BENZYL-3-FURYL)METHYL ESTER, TRANS-(±)-
Common Name English
DL-TRANS-RESMETHRIN
Common Name English
TRANS-RESMETHRIN
Common Name English
CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPEN-1-YL)-, (5-(PHENYLMETHYL)-3-FURANYL)METHYL ESTER, (1R,3R)-REL-
Common Name English
CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)-, (5-(PHENYLMETHYL)-3-FURANYL)METHYL ESTER, TRANS-(±)-
Common Name English
5-BENZYL-3-FURYLMETHYL (±)-TRANS-CHRYSANTHEMATE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID4091524
Created by admin on Mon Mar 31 21:00:31 GMT 2025 , Edited by admin on Mon Mar 31 21:00:31 GMT 2025
PRIMARY
FDA UNII
8535H601Y7
Created by admin on Mon Mar 31 21:00:31 GMT 2025 , Edited by admin on Mon Mar 31 21:00:31 GMT 2025
PRIMARY
CAS
10453-55-1
Created by admin on Mon Mar 31 21:00:31 GMT 2025 , Edited by admin on Mon Mar 31 21:00:31 GMT 2025
PRIMARY