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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 of DELTAMETHRIN

SMILES

CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C2=CC=CC(OC3=CC=CC=C3)=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
Molecular Formula C22H19Br2NO3
Molecular Weight 505.199
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 100.0 pM [IC50]
Modulator
846
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Preventing
Approved
8583
K-Othrine

Approved Use

K-Othrine is used for the control of malaria vector mosquitoes.
Preventing
Phase I
438
Unknown

Approved Use

Unknown
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26571224/
DELTAMETHRIN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 g single, oral
Accidental dose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
Other AEs: Dyspnea, Irritability...
Other AEs:
Dyspnea
Irritability
muscle cramps
Discomfort
Burning sensation
Loss of sensing
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
0.01 mg/kg single, oral
Highest studied dose
Dose: 0.01 mg/kg
Route: oral
Route: single
Dose: 0.01 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21035527/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21035527/
Sources:
https://pubmed.ncbi.nlm.nih.gov/21035527/
AEs

AEs

AESignificanceDosePopulation
Burning sensation
10 g single, oral
Accidental dose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
Discomfort
10 g single, oral
Accidental dose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
Dyspnea
10 g single, oral
Accidental dose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
Irritability
10 g single, oral
Accidental dose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
Loss of sensing
10 g single, oral
Accidental dose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
muscle cramps
10 g single, oral
Accidental dose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20568424/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

inducer
1087

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1741
CYP2C19
1119

CYP2B6
776

CES1
45

CYP1A1
389

CES2
33

P-gp
2052
CYP1A1
151

CYP2B6
669
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1932
 no
CYP1A1
272
 yes
CYP2B6
1160
 yes
CYP3A4
2633
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CES1
45
substrate
4014
Sources: httpspubmed.ncbi.nlm.nih.gov19326768
 major
CES2
33
substrate
4014
Sources: httpspubmed.ncbi.nlm.nih.gov19326768
 minor
CYP1A1
389
substrate
4014
Sources: httpspubmed.ncbi.nlm.nih.gov19326768
 minor
CYP2B6
776
substrate
4014
Sources: httpspubmed.ncbi.nlm.nih.gov19326768
 minor
CYP2C19
1119
substrate
4014
Sources: httpspubmed.ncbi.nlm.nih.gov19326768
 minor
CYP3A4
1946
substrate
4014
Sources: httpspubmed.ncbi.nlm.nih.gov19326768
 minor
P-gp
2052
 no
PubMed

PubMed

TitleDatePubMed
Estrogenicity of organophosphorus and pyrethroid pesticides.
2002-10-11
Age-dependent response to insecticides and enzymatic variation in susceptible and resistant codling moth larvae.
2002-10
Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin.
2002-09-25
Insecticide resistance in field populations of Frankliniella occidentalis (Pergande) in Murcia (south-east Spain).
2002-09
Field and laboratory selection of Frankliniella occidentalis (Pergande) for resistance to insecticides.
2002-09
Malaria control by residual insecticide spraying in Chingola and Chililabombwe, Copperbelt Province, Zambia.
2002-09
Pyrethroid exposure of the general population-is this due to diet.
2002-08-05
Biological monitoring of combined exposure to organophosphates and pyrethroids.
2002-08-05
Broad-spectrum insecticide resistance in obliquebanded leafroller Choristoneura rosaceana (Lepidoptera: Tortricidae) from Michigan.
2002-08
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).
2002-08
Fate of (14)C-labeled soybean and corn pesticides in tropical soils of Brazil under laboratory conditions.
2002-07-31
Determination of pyrethroid residues in tobacco and cigarette smoke by capillary gas chromatography.
2002-07-26
Alternative splicing of an insect sodium channel gene generates pharmacologically distinct sodium channels.
2002-07-01
Assessment of sorbent/water ratio effect on adsorption using dimensional analysis and batch experiments.
2002-07
Sub-lethal effects of deltamethrin on walking behaviour and response to host kairomone of the egg parasitoid Trissolcus basalis.
2002-07
Advantages of larval control for African malaria vectors: low mobility and behavioural responsiveness of immature mosquito stages allow high effective coverage.
2002-06-21
Screening for in vivo (anti)estrogenic and (anti)androgenic activities of technical and formulated deltamethrin.
2002-06
Use of liquid deltamethrin in modified, host-targeted bait tubes for control of fleas on sciurid rodents in northern California.
2002-06
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.
2002-06
Free bednets to pregnant women through antenatal clinics in Kenya: a cheap, simple and equitable approach to delivery.
2002-05
Effect of the synergist, piperonyl butoxide, on the development of deltamethrin resistance in yellow fever mosquito, Aedes aegypti L. (Diptera: Culicidae).
2002-05
Pesticide toxicity assessment using an electrochemical biosensor with Pseudomonas putida and a bioluminescence inhibition assay with Vibrio fischeri.
2002-04
Ultimobranchial gland of freshwater catfish, Heteropneustes fossilis in response to deltamethrin treatment.
2002-04
Field studies on the susceptibility of housefly to certain insecticides in nine Egyptian governorates.
2002-04
Chemical control of Penthaleus major (Acari: Prostigmata) in hayfields in Iceland.
2002-04
Effects of deltamethrin on lipid peroxidation in mice.
2002-04
Novel sodium channel gene mutations in Blattella germanica reduce the sensitivity of expressed channels to deltamethrin.
2002-04
Synergistic interaction between two cockroach sodium channel mutations and a tobacco budworm sodium channel mutation in reducing channel sensitivity to a pyrethroid insecticide.
2002-04
Levels of dichlorodiphenyltrichloroethane and deltamethrin in humans and environmental samples in malarious areas of Mexico.
2002-03
Sustainability of tsetse control by subsequent treatment of 10% of a previously treated Ugandan cattle population with 1% w/v deltamethrin.
2002-03
Comparative insecticidal power of three pyrethroids on netting.
2002-03
Effects of currently used pesticides in assays for estrogenicity, androgenicity, and aromatase activity in vitro.
2002-02-15
Cotton whitefly (Bemisia tabaci) resistance to organophosphate and pyrethroid insecticides in Pakistan.
2002-02
Fumigant activity of (E)-anethole identified in Illicium verum fruit against Blattella germanica.
2002-02
Effects of prenatal exposure to deltamethrin on forced swimming behavior, motor activity, and striatal dopamine levels in male and female rats.
2002-01-17
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
Physical and chemical properties of pyrethroids.
2002
Deltamethrin differentially affects neuronal subtypes in hippocampal primary culture.
2002
Topical insecticide treatments to protect dogs from sand fly vectors of leishmaniasis.
2001-12-19
Effects of nutritional and physiological status on behavioral avoidance of Anopheles minimus (Diptera: Culicidae) to DDT, deltamethrin and lambdacyhalothrin.
2001-12
Effect of pyrethroids on carbohydrate metabolic pathways in common carp, Cyprinus carpio.
2001-12
Evidence for an impact on the incidence of canine leishmaniasis by the mass use of deltamethrin-impregnated dog collars in southern Italy.
2001-12
Malaria control--two years' use of insecticide-treated bednets compared with insecticide house spraying in KwaZulu-Natal.
2001-11
Pyrethroid resistance and cross-resistance in the German cockroach, Blattella germanica (L).
2001-11
Baseline toxicity of several pesticides to Hyaliodes vitripennis (Say) (Hemiptera: Miridae).
2001-11
Deltamethrin resistance in the codling moth (Lepidoptera: Tortricidae): inheritance and number of genes involved.
2001-10
Highly-substrate active isoenzyme acetylcholinesterase-II, in rosy eye mutant of Aedes aegypti mosquito.
2001-08
Investigation of malaria outbreak in Bahraich district, Uttar Pradesh.
2001-05
Serological investigation of granulocytic Ehrlichia infection in sheep in Norway.
2001
Oral toxicity of deltamethrin and fenvalerate in Swiss mice.
2001
Patents

Patents

JPH06294165A
1

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Human volunteer studies have been conducted by orally administering the pesticides deltamethrin (0.01 mg/kg/day) or pirimicarb (0.02 mg/kg/day) at the acceptable daily intake (ADI) together with chlorpyrifos-methyl (0.01 mg/kg/day), in order to investigate any potential interactions that may occur during dietary exposure. https://www.ncbi.nlm.nih.gov/pubmed/21035527
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:23:43 GMT 2025
Edited
by admin
on Mon Mar 31 18:23:43 GMT 2025
Record UNII
2JTS8R821G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DECAMETHRIN
Preferred Name English
DELTAMETHRIN
HSDB   INCI   ISO   MART.   MI   WHO-DD  
INCI  
Official Name English
DELTAMETHRIN [ISO]
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
(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
Created by admin on Mon Mar 31 18:23:43 GMT 2025 , Edited by admin on Mon Mar 31 18:23:43 GMT 2025
EPA PESTICIDE CODE 97805
Created by admin on Mon Mar 31 18:23:43 GMT 2025 , Edited by admin on Mon Mar 31 18:23:43 GMT 2025
WHO-ATC P03BA03
Created by admin on Mon Mar 31 18:23:43 GMT 2025 , Edited by admin on Mon Mar 31 18:23:43 GMT 2025
NCI_THESAURUS C737
Created by admin on Mon Mar 31 18:23:43 GMT 2025 , Edited by admin on Mon Mar 31 18:23:43 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID8020381
Created by admin on Mon Mar 31 18:23:43 GMT 2025 , Edited by admin on Mon Mar 31 18:23:43 GMT 2025
PRIMARY
FDA UNII
2JTS8R821G
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PRIMARY
DRUG BANK
DB13600
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PRIMARY
MESH
C017180
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PRIMARY
CAS
52918-63-5
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PRIMARY
SMS_ID
100000079519
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PRIMARY
EVMPD
SUB13539MIG
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PRIMARY
HSDB
6604
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PRIMARY
NCI_THESAURUS
C83658
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PRIMARY
ECHA (EC/EINECS)
258-256-6
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PRIMARY
DRUG CENTRAL
4378
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PRIMARY
PUBCHEM
40585
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PRIMARY
MERCK INDEX
m4158
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PRIMARY Merck Index
ChEMBL
CHEMBL1593566
Created by admin on Mon Mar 31 18:23:43 GMT 2025 , Edited by admin on Mon Mar 31 18:23:43 GMT 2025
PRIMARY
WIKIPEDIA
DELTAMETHRIN
Created by admin on Mon Mar 31 18:23:43 GMT 2025 , Edited by admin on Mon Mar 31 18:23:43 GMT 2025
PRIMARY
RXCUI
22374
Created by admin on Mon Mar 31 18:23:43 GMT 2025 , Edited by admin on Mon Mar 31 18:23:43 GMT 2025
PRIMARY RxNorm
CHEBI
4388
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PRIMARY
ALANWOOD
deltamethrin
Created by admin on Mon Mar 31 18:23:43 GMT 2025 , Edited by admin on Mon Mar 31 18:23:43 GMT 2025
PRIMARY
Related Record Type Details
Structure of DELTAMETHRIN
ACTIVE MOIETY
NIH
NCATS
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