ALLETHRIN

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)=CC1C(C(=O)OC2CC(=O)C(CC=C)=C2C)C1(C)C

InChI

InChIKey=ZCVAOQKBXKSDMS-UHFFFAOYSA-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

HIDE SMILES / InChI

Molecular Formula	C19H26O3
Molecular Weight	302.4079
Charge	0
Count

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
ATP-binding cassette sub-family G member 2 16 Target ID: CHEMBL5393 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8504	42.5 µM [IC50]
Canalicular multispecific organic anion transporter 1 21 Target ID: CHEMBL5748 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8504	48.2 µM [IC50]
Solute carrier organic anion transporter family member 1B1 32 Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8504	16.5 µM [IC50]
Solute carrier organic anion transporter family member 2B1 2 Target ID: CHEMBL1743124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Activator 1447	37.8 µM [EC50]
Multidrug and toxin extrusion protein 1 3 Target ID: CHEMBL1743126 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8504	50.2 µM [IC50]
Solute carrier family 22 member 1 18 Target ID: CHEMBL5685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8504	2.6 µM [IC50]

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:21:34 GMT 2025` Edited by `admin` on `Mon Mar 31 19:21:34 GMT 2025`
Record UNII	0X03II877M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALLETHRIN I

Preferred Name

English

ALLETHRIN

Common Name

English

ALLETHROLONE ESTER OF CHRYSANTHEMUMMONOCARBOXYLIC ACID

Common Name

English

CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYLPROPENYL)-, ESTER WITH 2-ALLYL-4-HYDROXY-3-METHYL-2-CYCLOPENTEN-1-ONE

Common Name

English

ALLETHRIN [HSDB]

Common Name

English

PYNAMIN

Brand Name

English

2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)CYCLOPROPANECARBOXYLIC ACID 2-METHYL-4-OXO-3-(2-PROPENYL)-2-CYCLOPENTEN-1-YL ESTER

Systematic Name

English

ALLETHRIN I [MI]

Common Name

English

Code System Code Type Description

SMS_ID

100000077999