DELTAMETHRIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H19Br2NO3
Molecular Weight	505.199
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C2=CC(OC3=CC=CC=C3)=CC=C2

InChI

InChIKey=OWZREIFADZCYQD-NSHGMRRFSA-N

InChI=1S/C22H19Br2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18+,20-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://sitem.herts.ac.uk/aeru/iupac/Reports/205.htm | http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500013597.pdf | http://www.inchem.org/documents/jmpr/jmpmono/v00pr04.htm | https://www.ncbi.nlm.nih.gov/pubmed/25981874

Deltamethrin (DLM) is a pyrethroid insecticide and veterinary treatment that is approved for use in the EU, Australia and the USA. It has a low aqueous solubility, is semi-volatile and has a low potential to leach to groundwater. It is not persistent in soil and is non-mobile. Deltamethrin is highly toxic to humans and other mammals and is a neurotoxin. It is relatively non-toxic to birds and earthworms although it presents a high risk to most aquatic organisms and honeybees. Recent in vitro and in vivo studies have shown that the deltamethrin have the potential to induce apoptogenic signaling pathways which plays an important role in the mechanism of anticancer action. Thus, deltamethrin thereof could have the potential to develop as an anticancer agent.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serine/threonine protein phosphatase PP2B-alpha catalytic subunit 1 Target ID: CHEMBL5278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10781439	Inhibitor 8297		100.0 pM [IC50]
voltage-gated sodium channel activity 12 Target ID: GO:0005248 Sources: https://www.vectorcontrol.bayer.com/Portfolio_and_Innovation/Indoor-Residual-Spraying/K-Othrine \| https://www.ncbi.nlm.nih.gov/pubmed/21710279	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27188467 https://www.ncbi.nlm.nih.gov/pubmed/25981874 https://www.ncbi.nlm.nih.gov/pubmed/23282171	Primary	Basic research	Unknown Approved Use Unknown
Malaria 95 Sources: https://clinicaltrials.gov/ct2/show/NCT02458066 https://www.ncbi.nlm.nih.gov/pubmed/17278660 http://www.allfordrugs.com/2014/10/27/deltamethrin-an-agrochemical-can-help-control-malaria/	Preventing	Approved 8429	K-Othrine Approved Use K-Othrine is used for the control of malaria vector mosquitoes.
Visceral leishmaniasis 6 Sources: https://clinicaltrials.gov/ct2/show/NCT03269006	Preventing	Phase I 428	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Serological investigation of granulocytic Ehrlichia infection in sheep in Norway.	2001	11887393
Oral toxicity of deltamethrin and fenvalerate in Swiss mice.	2001	11748884
Eradication of lice in cattle.	2001	11455904
Highly-substrate active isoenzyme acetylcholinesterase-II, in rosy eye mutant of Aedes aegypti mosquito.	2001 Aug	12018585
Effects of nutritional and physiological status on behavioral avoidance of Anopheles minimus (Diptera: Culicidae) to DDT, deltamethrin and lambdacyhalothrin.	2001 Dec	11813658
Effect of pyrethroids on carbohydrate metabolic pathways in common carp, Cyprinus carpio.	2001 Dec	11802603
Evidence for an impact on the incidence of canine leishmaniasis by the mass use of deltamethrin-impregnated dog collars in southern Italy.	2001 Dec	11776454
Interaction of tetramethrin and deltamethrin at the single sodium channel in rat hippocampal neurons.	2001 Jun	11456334
Deltamethrin tolerance & associated cross resistance in Aedes aegypti from Mysore.	2001 Mar	11525152
Toxico-kinetics, recovery efficiency and microsomal changes following administration of deltamethrin to black Bengal goats.	2001 Mar	11455663
Acaricide toxicity and resistance in larvae of different strains of Tetranychus urticae and Panonychus ulmi (Acari: Tetranychidae).	2001 Mar	11455655
Investigation of malaria outbreak in Bahraich district, Uttar Pradesh.	2001 May	11968953
Malaria control--two years' use of insecticide-treated bednets compared with insecticide house spraying in KwaZulu-Natal.	2001 Nov	11847921
Effects of prenatal exposure to deltamethrin on forced swimming behavior, motor activity, and striatal dopamine levels in male and female rats.	2001 Nov-Dec	11792535
Control of the buffalo fly Haematobia irritans exigua in India, using the pyrethroids deltamethrin and fenvalerate.	2001 Sep	11583455
Somatostatin inhibits exocytosis in rat pancreatic alpha-cells by G(i2)-dependent activation of calcineurin and depriming of secretory granules.	2001 Sep 1	11533141
Topical insecticide treatments to protect dogs from sand fly vectors of leishmaniasis.	2001 Sep-Oct	11747701
Influence of the polyphenolic tannic acid on the toxicity of the insecticide deltametihrin to fish. A comparative study examining both biochemical and cytopathological parameters.	2002	12371615
Physical and chemical properties of pyrethroids.	2002	12132343
Deltamethrin differentially affects neuronal subtypes in hippocampal primary culture.	2002	12044486
Pesticide toxicity assessment using an electrochemical biosensor with Pseudomonas putida and a bioluminescence inhibition assay with Vibrio fischeri.	2002 Apr	12194026
Field studies on the susceptibility of housefly to certain insecticides in nine Egyptian governorates.	2002 Apr	12049274
Chemical control of Penthaleus major (Acari: Prostigmata) in hayfields in Iceland.	2002 Apr	12020005
Effects of deltamethrin on lipid peroxidation in mice.	2002 Apr	11931506
Novel sodium channel gene mutations in Blattella germanica reduce the sensitivity of expressed channels to deltamethrin.	2002 Apr	11886779
Synergistic interaction between two cockroach sodium channel mutations and a tobacco budworm sodium channel mutation in reducing channel sensitivity to a pyrethroid insecticide.	2002 Apr	11886774
Broad-spectrum insecticide resistance in obliquebanded leafroller Choristoneura rosaceana (Lepidoptera: Tortricidae) from Michigan.	2002 Aug	12192909
Field-simulator studies of insecticide resistance to dimethylcarbamates and pyrethroids conferred by metabolic- and target site-based mechanisms in peach-potato aphids, Myzus persicae (Hemiptera: Aphididae).	2002 Aug	12192906
Pyrethroid exposure of the general population-is this due to diet.	2002 Aug 5	12191872
Biological monitoring of combined exposure to organophosphates and pyrethroids.	2002 Aug 5	12191869
Cotton whitefly (Bemisia tabaci) resistance to organophosphate and pyrethroid insecticides in Pakistan.	2002 Feb	11852647
Fumigant activity of (E)-anethole identified in Illicium verum fruit against Blattella germanica.	2002 Feb	11852640
Effects of currently used pesticides in assays for estrogenicity, androgenicity, and aromatase activity in vitro.	2002 Feb 15	11884232
Assessment of sorbent/water ratio effect on adsorption using dimensional analysis and batch experiments.	2002 Jul	12152744
Sub-lethal effects of deltamethrin on walking behaviour and response to host kairomone of the egg parasitoid Trissolcus basalis.	2002 Jul	12146166
Determination of pyrethroid residues in tobacco and cigarette smoke by capillary gas chromatography.	2002 Jul 26	12198849
Fate of (14)C-labeled soybean and corn pesticides in tropical soils of Brazil under laboratory conditions.	2002 Jul 31	12137486
Screening for in vivo (anti)estrogenic and (anti)androgenic activities of technical and formulated deltamethrin.	2002 Jun	12202052
Comparison of three pyrethroid treatments of top-sheets for malaria control in emergencies: entomological and user acceptance studies in an Afghan refugee camp in Pakistan.	2002 Jun	12109715
Advantages of larval control for African malaria vectors: low mobility and behavioural responsiveness of immature mosquito stages allow high effective coverage.	2002 Jun 21	12153709
Sustainability of tsetse control by subsequent treatment of 10% of a previously treated Ugandan cattle population with 1% w/v deltamethrin.	2002 Mar	11969108
Comparative insecticidal power of three pyrethroids on netting.	2002 Mar	11963974
Free bednets to pregnant women through antenatal clinics in Kenya: a cheap, simple and equitable approach to delivery.	2002 May	12000650
Effect of the synergist, piperonyl butoxide, on the development of deltamethrin resistance in yellow fever mosquito, Aedes aegypti L. (Diptera: Culicidae).	2002 May	11948970
Age-dependent response to insecticides and enzymatic variation in susceptible and resistant codling moth larvae.	2002 Oct	12232873
Estrogenicity of organophosphorus and pyrethroid pesticides.	2002 Oct 11	12396874
Insecticide resistance in field populations of Frankliniella occidentalis (Pergande) in Murcia (south-east Spain).	2002 Sep	12233190
Field and laboratory selection of Frankliniella occidentalis (Pergande) for resistance to insecticides.	2002 Sep	12233182
Malaria control by residual insecticide spraying in Chingola and Chililabombwe, Copperbelt Province, Zambia.	2002 Sep	12225502
Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin.	2002 Sep 25	12236674

Patents

Sample Use Guides

In Vivo Use Guide

Female BALB/c mice received deltamethrin in two daily oral doses; 6 mg/kg for 84 days and 15 mg/kg for 14 days.

Route of Administration: Oral

In Vitro Use Guide

DLM (10–50 uM) induced apoptosis in both murine thymocytes and splenocytes via activating mitochondrial caspase dependent signaling pathways. DLM (>100 uM) increased the Ca2+ level and caused apoptosis in normal rat neural cells. DLM at low concentration (5–10 uM) induced calcium dependent apoptogenic signaling pathways in OC2 human oral cancer cells.

Name

Type

Language

DELTAMETHRIN

Official Name

English

DELTAMETHRIN [ISO]

Common Name

English

DECAMETHRIN

Common Name

English

Deltamethrin [WHO-DD]

Common Name

English

DELTAMETHRIN [HSDB]

Common Name

English

DELTAMETHRIN [IARC]

Common Name

English

DELTAMETHRIN [MI]

Common Name

English

(S)-.ALPHA.-CYANO-3-PHENOXYBENZYL (1R,3S)-3-(2,2-DIBROMOVINYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE

Systematic Name

English

DELTAMETHRIN [MART.]

Common Name

English

DELTAMETHRIN [INCI]

Common Name

English

(S)-.ALPHA.-CYANO-3-PHENOXYBENZYL (1R,3R)-3-(2,2-DIBROMOVINYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE

Systematic Name

English

(S)-CYANO(3-PHENOXYPHENYL)METHYL (1R,3R)-3-(2,2-DIBROMOETHENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QP53AC11