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 8297	42.5 µM [IC50]
Canalicular multispecific organic anion transporter 1 21 Target ID: CHEMBL5748 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8297	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 8297	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 1430	37.8 µM [EC50]
Multidrug and toxin extrusion protein 1 3 Target ID: CHEMBL1743126 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8297	50.2 µM [IC50]
Solute carrier family 22 member 1 18 Target ID: CHEMBL5685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28099443	Inhibitor 8297	2.6 µM [IC50]

PubMed

Title	Date	PubMed
DDT myoclonus: sites and mechanism of action.	1984 Aug	6378651
Bioallethrin causes permanent changes in behavioural and muscarinic acetylcholine receptor variables in adult mice exposed neonatally to DDT.	1995 Jul 1	7589230
In vitro effects of the pyrethroid S-bioallethrin on lymphocytes and basophils from atopic and nonatopic subjects.	1998 Nov	9860237
Differential expression of muscarinic subtype mRNAs after exposure to neurotoxic pesticides.	1998 Nov-Dec	10192214
Pyrethroids and piperonyl-butoxide affect human T-lymphocytes in vitro.	1999 Jun 30	10414782
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
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
Influence of pyrethroids and piperonyl butoxide on the Ca(2+)-ATPase activity of rat brain synaptosomes and leukocyte membranes.	2005 Feb	15652757
Maternal hair--an appropriate matrix for detecting maternal exposure to pesticides during pregnancy.	2006 Jul	16584725
Neonatal exposure to brominated flame retardant BDE-47 reduces long-term potentiation and postsynaptic protein levels in mouse hippocampus.	2007 Jun	17589592
Impact of urban agriculture on malaria vectors in Accra, Ghana.	2008 Aug 4	18680565
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
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
Current and historically used pesticides in residential soil from 11 homes in Atlanta, Georgia, USA.	2010 May	20016886
Differential state-dependent modification of inactivation-deficient Nav1.6 sodium channels by the pyrethroid insecticides S-bioallethrin, tefluthrin and deltamethrin.	2012 Jun	22465659
Allethrin toxicity on human corneal epithelial cells involves mitochondrial pathway mediated apoptosis.	2013 Dec	24055895
Allethrin induces oxidative stress, apoptosis and calcium release in rat testicular carcinoma cells (LC540).	2014 Dec	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 Nov	23595975

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:48:28 GMT 2023` Edited by `admin` on `Fri Dec 15 18:48:28 GMT 2023`
Record UNII	0X03II877M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

ALLETHRIN I

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