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 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2325407	Binding Agent 1076
Testis-specific androgen-binding protein 6 Target ID: CHEMBL3305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2325407	Binding Agent 1076
voltage-gated chloride channel activity 1 Target ID: GO:0005247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14657519	Inhibitor 8504

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 8583	JACUTIN Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1197 CYP2C8 810 CYP2B6 776 CYP2C19 1119 CYP1A1 389

Drug as victim

Target	Modality	Activity
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18948380/	major
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18948380/	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18948380/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18948380/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18948380/	yes
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18948380/	yes
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18948380/	yes

PubMed

Title	Date	PubMed
Allethrin induces oxidative stress, apoptosis and calcium release in rat testicular carcinoma cells (LC540).	2014-12	25072698
Allethrin induced toxicity in the male reproductive tract of rats contributes to disruption in the transcription of genes involved in germ cell production.	2014-11	23595975
Allethrin toxicity on human corneal epithelial cells involves mitochondrial pathway mediated apoptosis.	2013-12	24055895
Differential state-dependent modification of inactivation-deficient Nav1.6 sodium channels by the pyrethroid insecticides S-bioallethrin, tefluthrin and deltamethrin.	2012-06	22465659
Effect of continuous inhalation of allethrin-based mosquito coil smoke in the male reproductive tract of rats.	2012-02	22356257
Environmental impact on vascular development predicted by high-throughput screening.	2011-11	21788198
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.	2011-09-14	21786822
Divergent actions of the pyrethroid insecticides S-bioallethrin, tefluthrin, and deltamethrin on rat Na(v)1.6 sodium channels.	2010-09-15	20624410
Field Evaluation of the Bio-Efficacy of Three Pyrethroid Based Coils against Wild Populations of Anthropophilic Mosquitoes in Northern Tanzania.	2010-05	20606965
Current and historically used pesticides in residential soil from 11 homes in Atlanta, Georgia, USA.	2010-05	20016886
Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program.	2010-03-15	20143881
Evidence for a separate mechanism of toxicity for the Type I and the Type II pyrethroid insecticides.	2009-11	19766671
Comparative functional observational battery study of twelve commercial pyrethroid insecticides in male rats following acute oral exposure.	2009-11	19748519
Evidence for dose-additive effects of pyrethroids on motor activity in rats.	2009-10	20019907
Use of biocidal products (insect sprays and electro-vaporizer) in indoor areas--exposure scenarios and exposure modeling.	2009-09	19345645
Pyrethroid insecticides: isoform-dependent hydrolysis, induction of cytochrome P450 3A4 and evidence on the involvement of the pregnane X receptor.	2009-05-15	19249324
Combined analysis of prenatal (maternal hair and blood) and neonatal (infant hair, cord blood and meconium) matrices to detect fetal exposure to environmental pesticides.	2009-01	19019354
Potential developmental neurotoxicity of pesticides used in Europe.	2008-10-22	18945337
Impact of urban agriculture on malaria vectors in Accra, Ghana.	2008-08-04	18680565
Neurotoxic implications of the agonistic action of CS-syndrome pyrethroids on the N-type Ca(v)2.2 calcium channel.	2008-06	18383452
A comparison of infant hair, cord blood and meconium analysis to detect fetal exposure to environmental pesticides.	2008-02	17949707
Treatment of rabbit cheyletiellosis with selamectin or ivermectin: a retrospective case study.	2008-01-02	18171479
Influence of pyrethroids and piperonyl butoxide on histamine release from isolated rat mast cells.	2007-11	17891335
Neonatal exposure to brominated flame retardant BDE-47 reduces long-term potentiation and postsynaptic protein levels in mouse hippocampus.	2007-06	17589592
The effects of combined exposure to the pyrethroids deltamethrin and S-bioallethrin on hippocampal inhibition and skeletal muscle hyperexcitability in rats.	2006-10-15	16875707
Enzyme-linked immunosorbent assay (ELISA) and sol-gel-based immunoaffinity purification (IAP) of the pyrethroid bioallethrin in food and environmental samples.	2006-09-06	16939301
Maternal hair--an appropriate matrix for detecting maternal exposure to pesticides during pregnancy.	2006-07	16584725
Structure-activity relationships for the action of 11 pyrethroid insecticides on rat Na v 1.8 sodium channels expressed in Xenopus oocytes.	2006-03-15	16051293
[Effect of S-bioallethrin on human lymphocyte].	2006-03	16546737
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.	2006-01	16567869
A case for revisiting the safety of pesticides: a closer look at neurodevelopment.	2006-01	16393651
Efficacy of thermal fog application of deltacide, a synergized mixture of pyrethroids, against Aedes aegypti, the vector of dengue.	2005-12	16359411
Developmental neurotoxicity of pyrethroid insecticides: critical review and future research needs.	2005-02	15687048
Influence of pyrethroids and piperonyl butoxide on the Ca(2+)-ATPase activity of rat brain synaptosomes and leukocyte membranes.	2005-02	15652757
Multiresidue method using SPME for the determination of various pesticides with different volatility in confined atmospheres.	2004-06	15085315
Assessing estrogenic activity of pyrethroid insecticides using in vitro combination assays.	2004-04	15118252
Differential effects of pyrethroids on volume-sensitive anion and organic osmolyte pathways.	2004-03	15008955
Mammalian voltage-gated calcium channels are potently blocked by the pyrethroid insecticide allethrin.	2004-03	14634047
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
Pyrethroid insecticides influence the signal transduction in T helper lymphocytes from atopic and nonatopic subjects.	2003-04	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.	2003-01-09	12518331
Effects of pyrethroid insecticides and estrogen on WNT10B proto-oncogene expression.	2002-11	12437293
QSAR studies of the pyrethroid insecticides. Part 3. A putative pharmacophore derived using methodology based on molecular dynamics and hierarchical cluster analysis.	2002-08	12413028
[Determination of optical purity of SR-bioallethrin enantiomers by chiral high performance liquid chromatography].	2001-11	12545465
Enhanced efficiency of electrostatically charged insecticide aerosols.	2001-05	11374160
Pyrethroids and piperonyl-butoxide affect human T-lymphocytes in vitro.	1999-06-30	10414782
In vitro effects of the pyrethroid S-bioallethrin on lymphocytes and basophils from atopic and nonatopic subjects.	1998-11	9860237
Bioallethrin causes permanent changes in behavioural and muscarinic acetylcholine receptor variables in adult mice exposed neonatally to DDT.	1995-07-01	7589230
DDT myoclonus: sites and mechanism of action.	1984-08	6378651

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 `Mon Mar 31 18:39:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:39:14 GMT 2025`
Record UNII	G79DM7O471
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIOALLETHRIN

Common Name

English

NSC-11782

Preferred Name

English

BIOALLETHRIN [MART.]

Common Name

English

DEPALLETHRIN

Common Name

English

Bioallethrin [WHO-DD]

Common Name

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