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

Details

Stereochemistry RACEMIC
Molecular Formula C10H19O6PS2
Molecular Weight 330.358
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MALATHION

SMILES

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

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 330.358
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

3.97094388E11
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
n = 34
Health Status: healthy
Age Group: 18-50 years
Sex: M+F
Population Size: 34
Sources:
1.8 g single, intravenous
Dose: 1.8 g
Route: intravenous
Route: single
Dose: 1.8 g
Sources:
healthy, 24 years
n = 1
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 1
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: Page: p. 24
healthy
1000 mg/kg single, oral
Lethal dose
Dose: 1000 mg/kg
Route: oral
Route: single
Dose: 1000 mg/kg
Sources: Page: p.20
healthy
DLT: Death...
Dose limiting toxicities:
Death
Sources: Page: p.20
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
n = 1
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 1
Sources:
Nausea DLT
1.8 g single, intravenous
Dose: 1.8 g
Route: intravenous
Route: single
Dose: 1.8 g
Sources:
healthy, 24 years
n = 1
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 1
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
n = 1
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 1
Sources:
Death DLT
1000 mg/kg single, oral
Lethal dose
Dose: 1000 mg/kg
Route: oral
Route: single
Dose: 1000 mg/kg
Sources: Page: p.20
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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Comparative sensitivity of embryo-larval toxicity assays with African catfish (Clarias gariepinus) and zebra fish (Danio rerio).
2001
Malathion resistance and prevalence of the malathion carboxylesterase mechanism in populations of mosquito vectors of disease in Sri Lanka.
2001
Comparative residual toxicities of pesticides to the predator Agistemus industani (Acari: Stigmaeidae) on citrus in Florida.
2001
Interventions for treating headlice.
2001
Eradication of lice in cattle.
2001
[Cloning and fusion expression of detoxifying gene in Escherichia coli].
2001
Effects of local blood flow on the percutaneous absorption of the organophosphorus compound malathion: a microdialysis study in man.
2001 Aug
Potential for areawide integrated management of Mediterranean fruit fly (Diptera: Tephritidae) with a braconid parasitoid and a novel bait spray.
2001 Aug
Gas chromatographic method for assessing the dermal exposure of greenhouse applicators to dimethoate and malathion.
2001 Aug
Changes in concentration of pesticide residues in potatoes during washing and home preparation.
2001 Aug
Quebec clears way for use of aerial pesticides to combat West Nile virus.
2001 Aug 21
Cytogenetic monitoring of croatian population occupationally exposed to a complex mixture of pesticides.
2001 Aug 28
Case of the month. Suspicion--an important EMS asset.
2001 Dec
Chemomorphic analysis of malathion in skin layers of the rat: implications for the use of dermatopharmacokinetic tape stripping in exposure assessment to pesticides.
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
[Factors that modify the larval indices of Aedes aegypti in Colima, Mexico].
2001 Jul
Pesticide induced alterations in acetylcholine esterase and gamma glutamyl transpeptidase activities and glutathione level in lymphocytes of human poisoning cases.
2001 Jul
Probing the active sites of butyrylcholinesterase and cholesterol esterase with isomalathion: conserved stereoselective inactivation of serine hydrolases structurally related to acetylcholinesterase.
2001 Jul
[Detection of O,O,S-trimethyl phosphorodithioate, an impurity in phenthoate (PAP), in komatsuna].
2001 Jun
Measurement of children's exposure to pesticides: analysis of urinary metabolite levels in a probability-based sample.
2001 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
Detection of insecticide resistance in Aedes aegypti (Diptera: Culicidae) from Cuba and Venezuela.
2001 Sep
Deltamethrin treated bednets for control of malaria transmitted by Anopheles culicifacies (Diptera: Culicidae) in India.
2001 Sep
Sex-related response to organophosphorus and carbamate insecticides in adult Oriental fruit moth, Grapholita molesta.
2001 Sep
Effects of atrazine on acetylcholinesterase activity in midges (Chironomus tentans) exposed to organophosphorus insecticides.
2001 Sep
The impact of indoor residual spraying with malathion on malaria in refugee camps in eastern Sudan.
2001 Sep 1
High-performance liquid chromatographic separation of the enantiomers of organophosphorus pesticides on polysaccharide chiral stationary phases.
2001 Sep 14
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
Solid-phase microextraction coupled to gas chromatography-mass spectrometry for the study of soil adsorption coefficients of organophosphorus pesticides.
2002 Aug
Monitoring of pesticide applicators for potential dermal exposure to malathion and biomarkers in urine.
2002 Aug 5
Biological monitoring of exposure to organophosphate pesticides.
2002 Aug 5
Comparative in vitro pediculicidal efficacy of treatments in a resistant head lice population in the United States.
2002 Feb
Educational campaign versus malathion spraying for the control of Aedes aegypti in Colima, Mexico.
2002 Feb
Residues of methamidofos, malathion, and methiocarb in greenhouse crops.
2002 Feb 27
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
Transformation of Enterobacter gergoviae isolated from pink bollworm (Lepidoptera: Gelechiidae) gut with Bacillus thuringiensis toxin.
2002 Jan
Increased T-lymphocyte dependent antibody production in female SJL/J mice following exposure to commercial grade malathion.
2002 Jan 15
Cytogenetic studies on the effect of feeding mice with stored wheat grains treated with malathion.
2002 Jan 15
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
Removal of lindane and malathion from wastewater using bagasse fly ash--a sugar industry waste.
2002 May
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 Thu Jul 06 01:36:49 UTC 2023
Edited
by admin
on Thu Jul 06 01:36:49 UTC 2023
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 [ORANGE BOOK]
Common Name English
MALATHION [MI]
Common Name English
MALATHION [IARC]
Common Name English
Malathion [WHO-DD]
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 Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
NCI_THESAURUS C29727
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
EPA PESTICIDE CODE 57701
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
WHO-ATC P03AX03
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
WHO-VATC QP53AF12
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
NDF-RT N0000000177
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
Code System Code Type Description
NSC
6524
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
CAS
121-75-5
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200468
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
HSDB
665
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
ALANWOOD
malathion
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
EVMPD
SUB14453MIG
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
EPA CompTox
DTXSID4020791
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
LACTMED
Malathion
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-497-7
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
CHEBI
6651
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
NCI_THESAURUS
C47593
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
MERCK INDEX
M7034
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY Merck Index
RXCUI
6606
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY RxNorm
DAILYMED
U5N7SU872W
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
SMS_ID
100000076812
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
PUBCHEM
4004
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
DRUG BANK
DB00772
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
FDA UNII
U5N7SU872W
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
RS_ITEM_NUM
1374408
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
WIKIPEDIA
MALATHION
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
MESH
D008294
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
PRIMARY
DRUG CENTRAL
1626
Created by admin on Thu Jul 06 01:36:49 UTC 2023 , Edited by admin on Thu Jul 06 01:36:49 UTC 2023
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.
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IMPURITY -> PARENT
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY