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

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
Organ procurement and successful transplantation after malathion poisoning.
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
Interventions for treating head lice.
2001
Clinical features of patients with acute organophosphate poisoning requiring intensive care.
2001 Apr
Fitness consequences of malathion-specific resistance in red flour beetle (Coleoptera: Tenebrionidae) and selection for resistance in the absence of malathion.
2001 Apr
Distribution and abundance of insecticide resistant greenbugs (Homoptera: Aphididae) and validation of a bioassay to assess resistance.
2001 Apr
Effects of local blood flow on the percutaneous absorption of the organophosphorus compound malathion: a microdialysis study in man.
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
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
Effects of malathion on survival, growth, development, and equilibrium posture of bullfrog tadpoles (Rana catesbeiana).
2001 Jan
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
Behaviour of some organophosphorus and organochlorine pesticides in potatoes during soaking in different solutions.
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
Biochemical mechanisms of resistance in strains of Oryzaephilus surinamensis (Coleoptera: Silvanidae) resistant to malathion and chlorpyrifos-methyl.
2001 Jun
Balancing the risks: vector control and pesticide use in response to emerging illness.
2001 Jun
The role of glutathione S-transferases in the detoxification of some organophosphorus insecticides in larvae and pupae of the yellow mealworm, Tenebrio molitor (Coleoptera: Tenebrionidae).
2001 Jun
Effects of Anabaena spiroides (Cyanobacteria) aqueous extracts on the acetylcholinesterase activity of aquatic species.
2001 Jun
Susceptibility of sand flies to selected insecticides in North Africa and the Middle East.
2001 Mar
Efficacy of ground-applied ultra-low-volume malathion on honey bee survival and productivity in open and forest areas.
2001 Mar
Topical application as a method for comparing the effectiveness of insecticides against cat flea (Siphonaptera: Pulicidae).
2001 Mar
Bionomics of Anopheles sacharovi in Ardebil province, northwestern Iran during a larval control program.
2001 Mar 30
New method for determination of ten pesticides in human blood.
2001 Mar-Apr
A rat mammary tumor model induced by the organophosphorous pesticides parathion and malathion, possibly through acetylcholinesterase inhibition.
2001 May
Inhibition of lysyl hydroxylase by malathion and malaoxon.
2001 May 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
The impact of indoor residual spraying with malathion on malaria in refugee camps in eastern Sudan.
2001 Sep 1
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
Biological monitoring of exposure to organophosphate pesticides.
2002 Aug 5
General anaesthesia for emergency surgery during acute organophosphate poisoning.
2002 Feb
Embryo-larval toxicity tests with the African catfish (Clarias gariepinus): comparative sensitivity of endpoints.
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
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
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
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.
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY