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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

Description

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

CNS Active
3913
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

Elliott, M.
2
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Long-term effectiveness of grain protectants and structural treatments against Liposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of stored products.
2002 Dec
Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin.
2002 Sep 25
Structure-activity and interaction effects of 14 different pyrethroids on voltage-gated chloride ion channels.
2004 Feb
Glutathione S-transferase and insecticide resistance in laboratory strains and field populations of Musca domestica.
2005 Aug
Impact of urban agriculture on malaria vectors in Accra, Ghana.
2008 Aug 4
In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms.
2009 Jan
Pyrethroid insecticides: isoform-dependent hydrolysis, induction of cytochrome P450 3A4 and evidence on the involvement of the pregnane X receptor.
2009 May 15
Evidence for dose-additive effects of pyrethroids on motor activity in rats.
2009 Oct
Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids.
2010 Jan
Patents

Patents

JP4673837B2
32

Sample Use Guides

In Vivo Use Guide
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 Sat Dec 16 01:47:14 GMT 2023
Edited
by admin
on Sat Dec 16 01:47:14 GMT 2023
Record UNII
8535H601Y7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RESMETHRIN, TRANS-(±)-
Common 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
3-FURANMETHANOL, 5-BENZYL-, 2,2-DIMETHYL-3-(2-METHYLPROPENYL)CYCLOPROPANECARBOXYLATE, 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
PUBCHEM
162381
Created by admin on Sat Dec 16 01:47:14 GMT 2023 , Edited by admin on Sat Dec 16 01:47:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID4091524
Created by admin on Sat Dec 16 01:47:14 GMT 2023 , Edited by admin on Sat Dec 16 01:47:14 GMT 2023
PRIMARY
FDA UNII
8535H601Y7
Created by admin on Sat Dec 16 01:47:14 GMT 2023 , Edited by admin on Sat Dec 16 01:47:14 GMT 2023
PRIMARY
CAS
10453-55-1
Created by admin on Sat Dec 16 01:47:14 GMT 2023 , Edited by admin on Sat Dec 16 01:47:14 GMT 2023
PRIMARY
NIH
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