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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26O3
Molecular Weight 338.44
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BIORESMETHRIN

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

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
The status and development of insecticide resistance in Danish populations of the housefly Musca domestica L.
2001 Jan
Enhanced efficiency of electrostatically charged insecticide aerosols.
2001 May
Field studies on the susceptibility of housefly to certain insecticides in nine Egyptian governorates.
2002 Apr
Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin.
2002 Sep 25
Glutathione S-transferase and insecticide resistance in laboratory strains and field populations of Musca domestica.
2005 Aug
Hydrolysis of pyrethroids by human and rat tissues: examination of intestinal, liver and serum carboxylesterases.
2007 May 15
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
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.
Name Type Language
BIORESMETHRIN
INCI   INN   ISO   MI  
INCI   INN  
Official Name English
bioresmethrin [INN]
Common Name English
BIORESMETHRIN [ISO]
Common Name English
(5-BENZYL-3-FURYL)METHYL (+)-TRANS-2,2-DIMETHYL-3-(2-METHYLPROPENYL)CYCLOPROPANECARBOXYLATE
Systematic Name English
BIORESMETHRIN [INCI]
Common Name English
RESMETHRIN (+)-TRANS-FORM [MI]
Common Name English
BIORESMETHRIN [MI]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 97802
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
NCI_THESAURUS C737
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID2034382
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PRIMARY
INN
5210
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PRIMARY
ChEMBL
CHEMBL2106605
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PRIMARY
MERCK INDEX
m9544
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PRIMARY
MERCK INDEX
m2505
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PRIMARY Merck Index
ECHA (EC/EINECS)
249-014-0
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
FDA UNII
YPP8YQZ13B
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PRIMARY
PUBCHEM
162381
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PRIMARY
EVMPD
SUB05840MIG
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PRIMARY
NCI_THESAURUS
C74338
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PRIMARY
SMS_ID
100000085889
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
ALANWOOD
bioresmethrin
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
CAS
28434-01-7
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of BIORESMETHRIN
NIH
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