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 Date3.97094388E11 |
||
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 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 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: Page: p. 24 |
healthy Health Status: healthy Sources: Page: p. 24 |
|
1000 mg/kg single, oral Lethal dose Dose: 1000 mg/kg Route: oral Route: single Dose: 1000 mg/kg Sources: Page: p.20 |
healthy Health Status: healthy Sources: Page: p.20 |
DLT: Death... Dose limiting toxicities: Death Sources: Page: p.20 |
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 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 Health Status: healthy Sources: Page: p.20 |
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 |
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Concentrations of pesticide residues in tissues of fish from Kolleru Lake in India. | 2001 |
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Organ procurement and successful transplantation after malathion poisoning. | 2001 |
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Malathion resistance and prevalence of the malathion carboxylesterase mechanism in populations of mosquito vectors of disease in Sri Lanka. | 2001 |
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Comparative residual toxicities of pesticides to the predator Agistemus industani (Acari: Stigmaeidae) on citrus in Florida. | 2001 |
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Interventions for treating headlice. | 2001 |
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Highly-substrate active isoenzyme acetylcholinesterase-II, in rosy eye mutant of Aedes aegypti mosquito. | 2001 Aug |
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Effects of local blood flow on the percutaneous absorption of the organophosphorus compound malathion: a microdialysis study in man. | 2001 Aug |
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Potential for areawide integrated management of Mediterranean fruit fly (Diptera: Tephritidae) with a braconid parasitoid and a novel bait spray. | 2001 Aug |
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Quebec clears way for use of aerial pesticides to combat West Nile virus. | 2001 Aug 21 |
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Cytogenetic monitoring of croatian population occupationally exposed to a complex mixture of pesticides. | 2001 Aug 28 |
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Case of the month. Suspicion--an important EMS asset. | 2001 Dec |
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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 |
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[Biologic effect of diflubenzuron on Blattella germanica (Dictyoptera: Blattellidae)]. | 2001 Jan-Apr |
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[Factors that modify the larval indices of Aedes aegypti in Colima, Mexico]. | 2001 Jul |
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An outbreak of Plasmodium falciparum malaria due to Anopheles minimus in central Assam, India. | 2001 Mar-Jun |
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Non-Hodgkin's lymphoma and specific pesticide exposures in men: cross-Canada study of pesticides and health. | 2001 Nov |
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Mechanism of inhibition of lysyl hydroxylase activity by the organophosphates malathion and malaoxon. | 2001 Nov 1 |
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Toxicological studies of organophosphate and pyrethroid insecticides for controlling the fruit fly Dacus ciliatus (Diptera: Tephritidae). | 2001 Oct |
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Protective effect of vitamin E in dimethoate and malathion induced oxidative stress in rat erythrocytes. | 2001 Sep |
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Organic pollutants in surface waters from Portugal using chemometric interpretation. | 2001 Sep |
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Sex-related response to organophosphorus and carbamate insecticides in adult Oriental fruit moth, Grapholita molesta. | 2001 Sep |
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Effects of atrazine on acetylcholinesterase activity in midges (Chironomus tentans) exposed to organophosphorus insecticides. | 2001 Sep |
|
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 |
|
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 |
|
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 |
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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 |
|
Increased T-lymphocyte dependent antibody production in female SJL/J mice following exposure to commercial grade 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 |
|
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 |
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
Sat Dec 17 00:17:27 UTC 2022
by
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on
Sat Dec 17 00:17:27 UTC 2022
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Record UNII |
U5N7SU872W
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175723
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NCI_THESAURUS |
C29727
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EPA PESTICIDE CODE |
57701
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WHO-ATC |
P03AX03
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WHO-VATC |
QP53AF12
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NDF-RT |
N0000000177
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121-75-5
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CHEMBL1200468
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665
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malathion
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Malathion
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MALATHION
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D008294
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> INHIBITOR |
Malathion inhibited CYP1A1/2 activities more than 90%.
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METABOLIC ENZYME -> INHIBITOR |
Malathion inhibited CYP1A1/2 activities more than 90%.
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METABOLIC ENZYME -> INHIBITOR |
Human hepatic CYP2C8 activities after incubation with different pesticides showed that CYP2C8 activities were inhibited extensively by malathion (100,90%).
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METABOLIC ENZYME -> INHIBITOR |
Extensive inhibitions of CYP2A6-associated activity (94–98%) were observed with malathion
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METABOLIC ENZYME -> INHIBITOR |
CYP2C9 activity was extensively inhibited (more than 90% inhibition) by organophosphorus insecticides malathion
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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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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |