BIOALLETHRIN

Details

Stereochemistry	EPIMERIC
Molecular Formula	C19H26O3
Molecular Weight	302.4079
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)=C[C@@H]1[C@@H](C(=O)OC2CC(=O)C(CC=C)=C2C)C1(C)C

InChI

InChIKey=ZCVAOQKBXKSDMS-AQYZNVCMSA-N

InChI=1S/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3/t14-,16?,17+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H26O3
Molecular Weight	302.4079
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.who.int/whopes/quality/Bioallethrin_%20spec_eval_May2005.pdf?ua=1
Curator's Comment: Description was created based on several sources, including http://www.apotheken-umschau.de/Medikamente/Beipackzettel/Jacutin-Pedicul-Spray-3656327.html

Bioallethrin is a synthetic pyrethroid with fast knock-down activity against household pest insects. It is used in public health against mosquitoes, houseflies and cockroaches. Bioallethrin is a mixture of two of the allethrin isomers, [1R,trans;1R] and [1R,trans;1S] in an approximate ratio of 1:1. Bioallethrin is used as a component of spray for the treatment of pediculosis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2325407	Binding Agent 1064
Testis-specific androgen-binding protein 6 Target ID: CHEMBL3305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2325407	Binding Agent 1064
voltage-gated chloride channel activity 1 Target ID: GO:0005247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14657519	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pediculosis 9 Sources: http://www.apotheken-umschau.de/Medikamente/Beipackzettel/Jacutin-Pedicul-Spray-3656327.html https://www.drugs.com/international/jacutin.html	Curative		Approved 8429	JACUTIN Approved Use Unknown

PubMed

Title	Date	PubMed
Bioallethrin causes permanent changes in behavioural and muscarinic acetylcholine receptor variables in adult mice exposed neonatally to DDT.	1995 Jul 1	7589230
Differential expression of muscarinic subtype mRNAs after exposure to neurotoxic pesticides.	1998 Nov-Dec	10192214
Enhanced efficiency of electrostatically charged insecticide aerosols.	2001 May	11374160
[Determination of optical purity of SR-bioallethrin enantiomers by chiral high performance liquid chromatography].	2001 Nov	12545465
QSAR studies of the pyrethroid insecticides. Part 3. A putative pharmacophore derived using methodology based on molecular dynamics and hierarchical cluster analysis.	2002 Aug	12413028
Effects of pyrethroid insecticides and estrogen on WNT10B proto-oncogene expression.	2002 Nov	12437293
Pyrethroid insecticides influence the signal transduction in T helper lymphocytes from atopic and nonatopic subjects.	2003 Apr	12755381
Critical analysis of potential body temperature confounders on neurochemical endpoints caused by direct dosing and maternal separation in neonatal mice: a study of bioallethrin and deltamethrin interactions with temperature on brain muscarinic receptors.	2003 Jan-Feb	12518331
Pyrethroid stimulation of ion transport across frog skin.	2003 Jun	12785591
Assessing estrogenic activity of pyrethroid insecticides using in vitro combination assays.	2004 Apr	15118252
Structure-activity and interaction effects of 14 different pyrethroids on voltage-gated chloride ion channels.	2004 Feb	14657519
Differential effects of pyrethroids on volume-sensitive anion and organic osmolyte pathways.	2004 Mar	15008955
Mammalian voltage-gated calcium channels are potently blocked by the pyrethroid insecticide allethrin.	2004 Mar	14634047
Developmental neurotoxicity of pyrethroid insecticides: critical review and future research needs.	2005 Feb	15687048
Influence of pyrethroids and piperonyl butoxide on the Ca(2+)-ATPase activity of rat brain synaptosomes and leukocyte membranes.	2005 Feb	15652757
Ultra low volume aerosol application of deltacide (deltamethrin 0.5% w/v, S-bioallethrin 0.71% w/v & piperonyl butoxide 8.9% w/v) against mosquitoes.	2006 Jan	16567869
The effects of combined exposure to the pyrethroids deltamethrin and S-bioallethrin on hippocampal inhibition and skeletal muscle hyperexcitability in rats.	2006 Oct 15	16875707
Enzyme-linked immunosorbent assay (ELISA) and sol-gel-based immunoaffinity purification (IAP) of the pyrethroid bioallethrin in food and environmental samples.	2006 Sep 6	16939301
Influence of pyrethroids and piperonyl butoxide on histamine release from isolated rat mast cells.	2007 Nov	17891335
A comparison of infant hair, cord blood and meconium analysis to detect fetal exposure to environmental pesticides.	2008 Feb	17949707
Neurotoxic implications of the agonistic action of CS-syndrome pyrethroids on the N-type Ca(v)2.2 calcium channel.	2008 Jun	18383452
Potential developmental neurotoxicity of pesticides used in Europe.	2008 Oct 22	18945337
Combined analysis of prenatal (maternal hair and blood) and neonatal (infant hair, cord blood and meconium) matrices to detect fetal exposure to environmental pesticides.	2009 Jan	19019354
Pyrethroid insecticides: isoform-dependent hydrolysis, induction of cytochrome P450 3A4 and evidence on the involvement of the pregnane X receptor.	2009 May 15	19249324
Evidence for a separate mechanism of toxicity for the Type I and the Type II pyrethroid insecticides.	2009 Nov	19766671
Comparative functional observational battery study of twelve commercial pyrethroid insecticides in male rats following acute oral exposure.	2009 Nov	19748519
Evidence for dose-additive effects of pyrethroids on motor activity in rats.	2009 Oct	20019907
Use of biocidal products (insect sprays and electro-vaporizer) in indoor areas--exposure scenarios and exposure modeling.	2009 Sep	19345645
Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program.	2010 Mar 15	20143881
Field Evaluation of the Bio-Efficacy of Three Pyrethroid Based Coils against Wild Populations of Anthropophilic Mosquitoes in Northern Tanzania.	2010 May	20606965
Current and historically used pesticides in residential soil from 11 homes in Atlanta, Georgia, USA.	2010 May	20016886
Environmental impact on vascular development predicted by high-throughput screening.	2011 Nov	21788198
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.	2011 Sep 14	21786822
Effect of continuous inhalation of allethrin-based mosquito coil smoke in the male reproductive tract of rats.	2012 Feb	22356257
Differential state-dependent modification of inactivation-deficient Nav1.6 sodium channels by the pyrethroid insecticides S-bioallethrin, tefluthrin and deltamethrin.	2012 Jun	22465659

Patents

Sample Use Guides

In Vivo Use Guide

Bioallethrin is used as a component of spray for the treatment of pediculosis

Route of Administration: Topical

In Vitro Use Guide

In the anti-estrogenic activity test bioallethrin significantly inhibited 17beta-estradiol-induced MCF-7 BUS cell proliferation at 1 uM

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:00:47 GMT 2023` Edited by `admin` on `Fri Dec 15 17:00:47 GMT 2023`
Record UNII	G79DM7O471
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIOALLETHRIN

Common Name

English

BIOALLETHRIN [MART.]

Common Name

English

DEPALLETHRIN

Common Name

English

Bioallethrin [WHO-DD]

Common Name

English

NSC-11782

Code

English

2-METHYL-4-OXO-3-(2-PROPEN-1-YL)-2-CYCLOPENTEN-1-YL 2,2-DIMETHYL-3-(2-METHYL-1-PROPEN-1-YL)CYCLOPROPANECARBOXYLATE

Systematic Name

English

TRANS-ALLETHRIN

Common Name

English

ALLETHRIN [ISO]

Common Name

English

ESBIOTHRIN

Common Name

English

(RS)-3-ALLYL-2-METHYL-4-OXOCYCLOPENT-2-ENYL (1R,3R)-2,2-DIMETHYL-3-(2-METHYLPROP-1-ENYL)CYCLOPROPANECARBOXYLATE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

P03AC02