BIORESMETHRIN

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 Search

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
Sources: https://books.google.ru/books?id=vnaodM75BGsC&pg=PA29&lpg=PA29&dq=BIORESMETHRIN p.29 | http://www.bbsrc.ac.uk/documents/pyrethroid-timeline-pdf/ | http://www.inchem.org/documents/ukpids/ukpids/ukpid48.htm | http://www.t3db.ca/toxins/T3D1844

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
sodium channel activity 16 Target ID: GO:0005272 Sources: http://www.inchem.org/documents/ukpids/ukpids/ukpid48.htm \| https://www.ncbi.nlm.nih.gov/pubmed/6130027 \| http://www.genome.jp/dbget-bin/www_bget?C16810 \| http://www.t3db.ca/toxins/T3D1844	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids.	2010-01	19761868
Evidence for dose-additive effects of pyrethroids on motor activity in rats.	2009-10	20019907
Pyrethroid insecticides: isoform-dependent hydrolysis, induction of cytochrome P450 3A4 and evidence on the involvement of the pregnane X receptor.	2009-05-15	19249324
In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms.	2009-01	18948380
Impact of urban agriculture on malaria vectors in Accra, Ghana.	2008-08-04	18680565
Susceptibility to thiamethoxam of Musca domestica from Danish livestock farms.	2008-02	17972302
Hydrolysis of pyrethroids by human and rat tissues: examination of intestinal, liver and serum carboxylesterases.	2007-05-15	17442360
Human carboxylesterases and their role in xenobiotic and endobiotic metabolism.	2007	17936933
Identification and quantitation of pyrethroid pesticide residues in vegetables by solid-phase extraction and liquid chromatography/electrospray ionization ion trap mass spectrometry.	2007	17510928
Hydrolytic metabolism of pyrethroids by human and other mammalian carboxylesterases.	2006-02-28	16387282
Glutathione S-transferase and insecticide resistance in laboratory strains and field populations of Musca domestica.	2005-08	16156589
Structure-activity and interaction effects of 14 different pyrethroids on voltage-gated chloride ion channels.	2004-02	14657519
Pyrethroid stimulation of ion transport across frog skin.	2003-06	12785591
Synergized bifenthrin plus chlorpyrifos-methyl for control of beetles and psocids in sorghum in Australia.	2003-04	14994824
Long-term effectiveness of grain protectants and structural treatments against Liposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of stored products.	2002-12	12476995
Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin.	2002-09-25	12236674
Field studies on the susceptibility of housefly to certain insecticides in nine Egyptian governorates.	2002-04	12049274
Enhanced efficiency of electrostatically charged insecticide aerosols.	2001-05	11374160
The status and development of insecticide resistance in Danish populations of the housefly Musca domestica L.	2001-01	11455636

Patents

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

Official Name

English

BIORESMETHRIN [ISO]

Preferred Name

English

bioresmethrin [INN]

Common Name

English

(5-BENZYL-3-FURYL)METHYL (+)-TRANS-2,2-DIMETHYL-3-(2-METHYLPROPENYL)CYCLOPROPANECARBOXYLATE

Systematic Name

English

RESMETHRIN (+)-TRANS-FORM [MI]

Common Name

English

BIORESMETHRIN [MI]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

97802