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
In vitro effects of the pyrethroid S-bioallethrin on lymphocytes and basophils from atopic and nonatopic subjects.	1998 Nov	9860237
[Determination of optical purity of SR-bioallethrin enantiomers by chiral high performance liquid chromatography].	2001 Nov	12545465
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
Multiresidue method using SPME for the determination of various pesticides with different volatility in confined atmospheres.	2004 Jun	15085315
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
Efficacy of thermal fog application of deltacide, a synergized mixture of pyrethroids, against Aedes aegypti, the vector of dengue.	2005 Dec	16359411
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
[Effect of S-bioallethrin on human lymphocyte].	2006 Mar	16546737
Structure-activity relationships for the action of 11 pyrethroid insecticides on rat Na v 1.8 sodium channels expressed in Xenopus oocytes.	2006 Mar 15	16051293
Influence of pyrethroids and piperonyl butoxide on histamine release from isolated rat mast cells.	2007 Nov	17891335
Impact of urban agriculture on malaria vectors in Accra, Ghana.	2008 Aug 4	18680565
A comparison of infant hair, cord blood and meconium analysis to detect fetal exposure to environmental pesticides.	2008 Feb	17949707
Treatment of rabbit cheyletiellosis with selamectin or ivermectin: a retrospective case study.	2008 Jan 2	18171479
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
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.	2011 Sep 14	21786822
Allethrin induced toxicity in the male reproductive tract of rats contributes to disruption in the transcription of genes involved in germ cell production.	2014 Nov	23595975

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