U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C10H19O6PS2
Molecular Weight 330.3606
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MALATHION

SMILES

CCOC(=O)CC(C(=O)OCC)SP(=S)(OC)OC

InChI

InChIKey=JXSJBGJIGXNWCI-UHFFFAOYSA-N
InChI=1S/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(18,13-3)14-4/h8H,5-7H2,1-4H3

HIDE SMILES / InChI

Molecular Formula C10H19O6PS2
Molecular Weight 330.3606
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Malathion is an organophosphate insecticide, an inhibitor of cholinesterase. In low doses (0.5%) malathion is used for treatment of pediculosis and scabies.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
OVIDE

Approved Use

Malathion lotion is indicated for patients infected with Pediculus humanus capitis (head lice and their ova) of the scalp hair.

Launch Date

397094400000
Curative
DERBAC M

Approved Use

Malathion is used for topical treatment of scabies, usually as an aqueous lotion.
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.89 h
1.8 g single, intravenous
dose: 1.8 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MALATHION serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
15 mg/kg single, oral
Highest studied dose
healthy, 18-50 years
1.8 g single, intravenous
Dose: 1.8 g
Route: intravenous
Route: single
Dose: 1.8 g
Sources:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
DLT: Headache, Nausea...
Dose limiting toxicities:
Headache
Nausea
Urination abnormal NOS
Sources:
85 mg/m3 single, respiratory
Highest studied dose
Dose: 85 mg/m3
Route: respiratory
Route: single
Dose: 85 mg/m3
Sources:
healthy
1000 mg/kg single, oral
Lethal dose
Dose: 1000 mg/kg
Route: oral
Route: single
Dose: 1000 mg/kg
Sources:
healthy
DLT: Death...
AEs

AEs

AESignificanceDosePopulation
Headache DLT
1.8 g single, intravenous
Dose: 1.8 g
Route: intravenous
Route: single
Dose: 1.8 g
Sources:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
Nausea DLT
1.8 g single, intravenous
Dose: 1.8 g
Route: intravenous
Route: single
Dose: 1.8 g
Sources:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
Urination abnormal NOS DLT
1.8 g single, intravenous
Dose: 1.8 g
Route: intravenous
Route: single
Dose: 1.8 g
Sources:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
Death DLT
1000 mg/kg single, oral
Lethal dose
Dose: 1000 mg/kg
Route: oral
Route: single
Dose: 1000 mg/kg
Sources:
healthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
strong [IC50 2.5 uM]
yes [IC50 114.2 uM]
Drug as victim
Sourcing
PubMed

PubMed

TitleDatePubMed
Comparative sensitivity of embryo-larval toxicity assays with African catfish (Clarias gariepinus) and zebra fish (Danio rerio).
2001
Concentrations of pesticide residues in tissues of fish from Kolleru Lake in India.
2001
Organ procurement and successful transplantation after malathion poisoning.
2001
Comparative residual toxicities of pesticides to the predator Agistemus industani (Acari: Stigmaeidae) on citrus in Florida.
2001
Interventions for treating headlice.
2001
Highly-substrate active isoenzyme acetylcholinesterase-II, in rosy eye mutant of Aedes aegypti mosquito.
2001 Aug
Case of the month. Suspicion--an important EMS asset.
2001 Dec
Gas chromatographic-tandem mass spectrometric analytical method for the study of inhalation, potential dermal and actual exposure of agricultural workers to the pesticide malathion.
2001 Dec 21
[Biologic effect of diflubenzuron on Blattella germanica (Dictyoptera: Blattellidae)].
2001 Jan-Apr
[Detection of O,O,S-trimethyl phosphorodithioate, an impurity in phenthoate (PAP), in komatsuna].
2001 Jun
An outbreak of Plasmodium falciparum malaria due to Anopheles minimus in central Assam, India.
2001 Mar-Jun
Non-Hodgkin's lymphoma and specific pesticide exposures in men: cross-Canada study of pesticides and health.
2001 Nov
Mechanism of inhibition of lysyl hydroxylase activity by the organophosphates malathion and malaoxon.
2001 Nov 1
Toxicological studies of organophosphate and pyrethroid insecticides for controlling the fruit fly Dacus ciliatus (Diptera: Tephritidae).
2001 Oct
Thiols and polyamines in the potentiation of malathion toxicity in larval stages of the toad Bufo arenarum.
2001 Oct
Identification of butyrylcholinesterase adducts after inhibition with isomalathion using mass spectrometry: difference in mechanism between (1R)- and (1S)-stereoisomers.
2001 Oct 15
Protective effect of vitamin E in dimethoate and malathion induced oxidative stress in rat erythrocytes.
2001 Sep
Organic pollutants in surface waters from Portugal using chemometric interpretation.
2001 Sep
Deltamethrin treated bednets for control of malaria transmitted by Anopheles culicifacies (Diptera: Culicidae) in India.
2001 Sep
High-performance liquid chromatographic separation of the enantiomers of organophosphorus pesticides on polysaccharide chiral stationary phases.
2001 Sep 14
Designing safer (soft) drugs by avoiding the formation of toxic and oxidative metabolites.
2002
Esterase patterns and phylogenetic relationships of Drosophila species in the saltans subgroup (saltans group).
2002
Age-related alteration in hepatic disposition of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and pesticides.
2002 Apr
Field studies on the susceptibility of housefly to certain insecticides in nine Egyptian governorates.
2002 Apr
Solid-phase microextraction coupled to gas chromatography-mass spectrometry for the study of soil adsorption coefficients of organophosphorus pesticides.
2002 Aug
Biological monitoring of exposure to organophosphate pesticides.
2002 Aug 5
General anaesthesia for emergency surgery during acute organophosphate poisoning.
2002 Feb
Comparative in vitro pediculicidal efficacy of treatments in a resistant head lice population in the United States.
2002 Feb
Embryo-larval toxicity tests with the African catfish (Clarias gariepinus): comparative sensitivity of endpoints.
2002 Feb
Educational campaign versus malathion spraying for the control of Aedes aegypti in Colima, Mexico.
2002 Feb
Genotoxic effects of malathion: an organophosphorus insecticide, using three mammalian bioassays in vivo.
2002 Feb 15
Residues of methamidofos, malathion, and methiocarb in greenhouse crops.
2002 Feb 27
[Insecticide resistance of different populations of white-backed planthopper, Sogatella furcifera (Horváth) (Homoptera:Delphacidae)].
2002 Jan
Simple determination of 22 organophosphorous pesticides in human blood using headspace solid-phase microextraction and gas chromatography with mass spectrometric detection.
2002 Jan
Widespread insecticide resistance in head lice to the over-the-counter pediculocides in England, and the emergence of carbaryl resistance.
2002 Jan
Sister chromatid exchange and proliferative rate index in the longitudinal risk assessment of occupational exposure to pesticides.
2002 Jan
Transformation of Enterobacter gergoviae isolated from pink bollworm (Lepidoptera: Gelechiidae) gut with Bacillus thuringiensis toxin.
2002 Jan
Cytogenetic studies on the effect of feeding mice with stored wheat grains treated with malathion.
2002 Jan 15
Size exclusion chromatographic cleanup for GC/MS determination of organophosphorus pesticide residues in household and vehicle dust.
2002 Jan-Feb
Determination of insecticides in honey by matrix solid-phase dispersion and gas chromatography with nitrogen-phosphorus detection and mass spectrometric confirmation.
2002 Jan-Feb
Assessment of organophosphorous pesticide exposures in the diets of preschool children in Washington State.
2002 Jan-Feb
Factors influencing nominal effective concentrations of chemical compounds in vitro: medium protein concentration.
2002 Jun
Observations on the domestic ecology of Rhodnius ecuadoriensis (Triatominae).
2002 Mar
Chemical predictors of wheeze among farmer pesticide applicators in the Agricultural Health Study.
2002 Mar 1
Human blood and environmental media screening method for pesticides and polychlorinated biphenyl compounds using liquid extraction and gas chromatography-mass spectrometry analysis.
2002 Mar 25
Removal of lindane and malathion from wastewater using bagasse fly ash--a sugar industry waste.
2002 May
Controversies concerning the treatment of lice and scabies.
2002 May
Clinical practice. Head lice.
2002 May 23
Determination of pesticide residues in coconut water by liquid-liquid extraction and gas chromatography with electron-capture plus thermionic specific detection and solid-phase extraction and high-performance liquid chromatography with ultraviolet detection.
2002 May 31
Development of an in vitro test battery for the estimation of acute human systemic toxicity: An outline of the EDIT project. Evaluation-guided Development of New In Vitro Test Batteries.
2002 May-Jun
Patents

Sample Use Guides

In Vivo Use Guide
Malathion lotion should be applied on dry hair in amount just sufficient to thoroughly wet the hair and scalp. After 8 to 12 hours, the hair should be shampooed and rinsed.
Route of Administration: Topical
The activity of acetylcholinesterase was measured by the colorimetric method using acetylthiocholine iodide (ASChl) as the substrate and 5,5 dithiobis(2-nitrobenzoicacid) (DTNB), as the reagent. The enzyme activity was measured by following the increase in absorbance at 412 nm arising from the formation of the thionitrobenzoate anion in the enzyme catalysed reaction.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:55:07 UTC 2021
Edited
by admin
on Fri Jun 25 20:55:07 UTC 2021
Record UNII
U5N7SU872W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MALATHION
EP   HSDB   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
MALATHION [MART.]
Common Name English
ENT-17034
Code English
MALATHION [VANDF]
Common Name English
MALATHION [WHO-DD]
Common Name English
MALATHION [ORANGE BOOK]
Common Name English
MALATHION [MI]
Common Name English
MALATHION [IARC]
Common Name English
MALATHION [EP MONOGRAPH]
Common Name English
DIETHYL 2-((DIMETHOXYPHOSPHINOTHIOYL)THIO)BUTANEDIOATE
Systematic Name English
DIETHYL (+/-)-MERCAPTOSUCCINATE, S-ESTER WITH O,O-DIMETHYL PHOSPHORODITHIOATE
Common Name English
MALATHION [USP MONOGRAPH]
Common Name English
8059HC
Code English
BUTANEDIOIC ACID, ((DIMETHOXYPHOSPHINOTHIOYL)-THIO)-, DIETHYL ESTER, (+/-)-
Common Name English
DIETHYL (DIMETHOXYPHOSPHINOTHIOYLTHIO)SUCCINATE
Systematic Name English
MALATHION [HSDB]
Common Name English
ENT 17,034
Code English
NSC-6524
Code English
BUTANEDIOIC ACID, ((DIMETHOXYPHOSPHINOTHIOYL)THIO)-, DIETHYL ESTER
Common Name English
SUCCINIC ACID, MERCAPTO-, DIETHYL ESTER, S-ESTER WITH O,O-DIMETHYLPHOSPHORODITHIOATE
Common Name English
MALATHION [USP-RS]
Common Name English
OVIDE
Code English
Classification Tree Code System Code
NDF-RT N0000175723
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
NCI_THESAURUS C29727
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
EPA PESTICIDE CODE 57701
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
WHO-ATC P03AX03
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
WHO-VATC QP53AF12
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
NDF-RT N0000000177
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
Code System Code Type Description
CAS
121-75-5
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200468
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
HSDB
665
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
EVMPD
SUB14453MIG
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
EPA CompTox
121-75-5
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
LACTMED
Malathion
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-497-7
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
NCI_THESAURUS
C47593
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
MERCK INDEX
M7034
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY Merck Index
RXCUI
6606
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY RxNorm
PUBCHEM
4004
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
DRUG BANK
DB00772
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
FDA UNII
U5N7SU872W
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
USP_CATALOG
1374408
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
MALATHION
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
MESH
D008294
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
DRUG CENTRAL
1626
Created by admin on Fri Jun 25 20:55:07 UTC 2021 , Edited by admin on Fri Jun 25 20:55:07 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INHIBITOR
Malathion inhibited CYP1A1/2 activities more than 90%.
METABOLIC ENZYME -> INHIBITOR
Malathion inhibited CYP1A1/2 activities more than 90%.
METABOLIC ENZYME -> INHIBITOR
Human hepatic CYP2C8 activities after incubation with different pesticides showed that CYP2C8 activities were inhibited extensively by malathion (100,90%).
METABOLIC ENZYME -> INHIBITOR
Extensive inhibitions of CYP2A6-associated activity (94–98%) were observed with malathion
METABOLIC ENZYME -> INHIBITOR
CYP2C9 activity was extensively inhibited (more than 90% inhibition) by organophosphorus insecticides malathion
METABOLIC ENZYME -> INHIBITOR
Screening of potential CYP2B6 inhibitions illustrates that CYP2B6 activity was extensively inhibited by all tested organophosphate pesticides. Malathion and phenthoate resulted in 91% inhibition.
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY