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
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
| 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 | ( + / - ) |
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2362988 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22286807 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
Sources: https://www.drugs.com/pro/malathion.html |
Curative | OVIDE Approved UseMalathion lotion is indicated for patients infected with Pediculus humanus capitis (head lice and their ova) of the scalp hair. Launch Date1982 |
||
| Curative | DERBAC M Approved UseMalathion is used for topical treatment of scabies, usually as an aqueous lotion. |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.89 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3612901 |
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
| Dose | Population | Adverse events |
|---|---|---|
15 mg/kg single, oral Highest studied dose Dose: 15 mg/kg Route: oral Route: single Dose: 15 mg/kg Sources: |
healthy, 18-50 years Health Status: healthy Age Group: 18-50 years Sex: M+F Sources: |
|
1.8 g single, intravenous Dose: 1.8 g Route: intravenous Route: single Dose: 1.8 g Sources: |
healthy, 24 years |
DLT: Headache, Nausea... Dose limiting toxicities: Headache Sources: Nausea Urination abnormal NOS |
85 mg/m3 single, respiratory Highest studied dose Dose: 85 mg/m3 Route: respiratory Route: single Dose: 85 mg/m3 Sources: |
healthy Health Status: healthy Sources: |
|
1000 mg/kg single, oral Lethal dose Dose: 1000 mg/kg Route: oral Route: single Dose: 1000 mg/kg Sources: |
healthy Health Status: healthy Sources: |
DLT: Death... Dose limiting toxicities: Death Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Headache | DLT | 1.8 g single, intravenous Dose: 1.8 g Route: intravenous Route: single Dose: 1.8 g Sources: |
healthy, 24 years |
| Nausea | DLT | 1.8 g single, intravenous Dose: 1.8 g Route: intravenous Route: single Dose: 1.8 g Sources: |
healthy, 24 years |
| 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 |
| Death | DLT | 1000 mg/kg single, oral Lethal dose Dose: 1000 mg/kg Route: oral Route: single Dose: 1000 mg/kg Sources: |
healthy Health Status: healthy Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/20654334/ |
no | |||
| strong [IC50 2.5 uM] | ||||
| yes [IC50 114.2 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| yes | ||||
| yes | ||||
| yes | ||||
Page: 16.0 |
yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Monitoring of pesticide applicators for potential dermal exposure to malathion and biomarkers in urine. | 2002-08-05 |
|
| Biological monitoring of exposure to organophosphate pesticides. | 2002-08-05 |
|
| Solid-phase microextraction coupled to gas chromatography-mass spectrometry for the study of soil adsorption coefficients of organophosphorus pesticides. | 2002-08 |
|
| 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. | 2002-07-11 |
|
| Factors influencing nominal effective concentrations of chemical compounds in vitro: medium protein concentration. | 2002-06 |
|
| 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. | 2002-05-31 |
|
| Clinical practice. Head lice. | 2002-05-23 |
|
| Removal of lindane and malathion from wastewater using bagasse fly ash--a sugar industry waste. | 2002-05 |
|
| Controversies concerning the treatment of lice and scabies. | 2002-05 |
|
| An outbreak of Plasmodium falciparum malaria due to Anopheles minimus in central Assam, India. | 2002-04-20 |
|
| Age-related alteration in hepatic disposition of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and pesticides. | 2002-04 |
|
| Field studies on the susceptibility of housefly to certain insecticides in nine Egyptian governorates. | 2002-04 |
|
| Human blood and environmental media screening method for pesticides and polychlorinated biphenyl compounds using liquid extraction and gas chromatography-mass spectrometry analysis. | 2002-03-25 |
|
| Size exclusion chromatographic cleanup for GC/MS determination of organophosphorus pesticide residues in household and vehicle dust. | 2002-03-07 |
|
| Determination of insecticides in honey by matrix solid-phase dispersion and gas chromatography with nitrogen-phosphorus detection and mass spectrometric confirmation. | 2002-03-07 |
|
| Chemical predictors of wheeze among farmer pesticide applicators in the Agricultural Health Study. | 2002-03-01 |
|
| Observations on the domestic ecology of Rhodnius ecuadoriensis (Triatominae). | 2002-03 |
|
| Residues of methamidofos, malathion, and methiocarb in greenhouse crops. | 2002-02-27 |
|
| Genotoxic effects of malathion: an organophosphorus insecticide, using three mammalian bioassays in vivo. | 2002-02-15 |
|
| [Biologic effect of diflubenzuron on Blattella germanica (Dictyoptera: Blattellidae)]. | 2002-02-06 |
|
| General anaesthesia for emergency surgery during acute organophosphate poisoning. | 2002-02 |
|
| Comparative in vitro pediculicidal efficacy of treatments in a resistant head lice population in the United States. | 2002-02 |
|
| Embryo-larval toxicity tests with the African catfish (Clarias gariepinus): comparative sensitivity of endpoints. | 2002-02 |
|
| Educational campaign versus malathion spraying for the control of Aedes aegypti in Colima, Mexico. | 2002-02 |
|
| Increased T-lymphocyte dependent antibody production in female SJL/J mice following exposure to commercial grade malathion. | 2002-01-15 |
|
| Cytogenetic studies on the effect of feeding mice with stored wheat grains treated with malathion. | 2002-01-15 |
|
| [Insecticide resistance of different populations of white-backed planthopper, Sogatella furcifera (Horváth) (Homoptera:Delphacidae)]. | 2002-01 |
|
| Simple determination of 22 organophosphorous pesticides in human blood using headspace solid-phase microextraction and gas chromatography with mass spectrometric detection. | 2002-01 |
|
| Widespread insecticide resistance in head lice to the over-the-counter pediculocides in England, and the emergence of carbaryl resistance. | 2002-01 |
|
| Sister chromatid exchange and proliferative rate index in the longitudinal risk assessment of occupational exposure to pesticides. | 2002-01 |
|
| Transformation of Enterobacter gergoviae isolated from pink bollworm (Lepidoptera: Gelechiidae) gut with Bacillus thuringiensis toxin. | 2002-01 |
|
| 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 |
|
| Gas chromatographic-tandem mass spectrometric analytical method for the study of inhalation, potential dermal and actual exposure of agricultural workers to the pesticide malathion. | 2001-12-21 |
|
| Case of the month. Suspicion--an important EMS asset. | 2001-12 |
|
| Chemomorphic analysis of malathion in skin layers of the rat: implications for the use of dermatopharmacokinetic tape stripping in exposure assessment to pesticides. | 2001-12 |
|
| Mechanism of inhibition of lysyl hydroxylase activity by the organophosphates malathion and malaoxon. | 2001-11-01 |
|
| Non-Hodgkin's lymphoma and specific pesticide exposures in men: cross-Canada study of pesticides and health. | 2001-11 |
|
| Identification of butyrylcholinesterase adducts after inhibition with isomalathion using mass spectrometry: difference in mechanism between (1R)- and (1S)-stereoisomers. | 2001-10-15 |
|
| Toxicological studies of organophosphate and pyrethroid insecticides for controlling the fruit fly Dacus ciliatus (Diptera: Tephritidae). | 2001-10 |
|
| Protective effect of vitamin E in dimethoate and malathion induced oxidative stress in rat erythrocytes. | 2001-09 |
|
| Organic pollutants in surface waters from Portugal using chemometric interpretation. | 2001-09 |
|
| Highly-substrate active isoenzyme acetylcholinesterase-II, in rosy eye mutant of Aedes aegypti mosquito. | 2001-08 |
|
| Assessment of organophosphorous pesticide exposures in the diets of preschool children in Washington State. | 2001-04-20 |
|
| 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 |
|
| 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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/malathion.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18476213
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
Edited
Mon Mar 31 19:11:46 GMT 2025
by
admin
on
Mon Mar 31 19:11:46 GMT 2025
|
| Record UNII |
U5N7SU872W
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NDF-RT |
N0000175723
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
||
|
NCI_THESAURUS |
C29727
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
||
|
EPA PESTICIDE CODE |
57701
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
||
|
WHO-ATC |
P03AX03
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
||
|
WHO-VATC |
QP53AF12
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
||
|
NDF-RT |
N0000000177
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
6524
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
121-75-5
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
CHEMBL1200468
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
665
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
malathion
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
SUB14453MIG
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
DTXSID4020791
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
Malathion
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
204-497-7
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
6651
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
C47593
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
m7034
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | Merck Index | ||
|
6606
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | RxNorm | ||
|
U5N7SU872W
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
100000076812
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
4004
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
DB00772
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
U5N7SU872W
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
1374408
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
MALATHION
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
D008294
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
PRIMARY | |||
|
1626
Created by
admin on Mon Mar 31 19:11:46 GMT 2025 , Edited by admin on Mon Mar 31 19:11:46 GMT 2025
|
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 |