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 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 |
|---|---|---|---|---|
| no | ||||
| strong [IC50 2.5 uM] | ||||
| yes [IC50 114.2 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| Highly-substrate active isoenzyme acetylcholinesterase-II, in rosy eye mutant of Aedes aegypti mosquito. | 2001 Aug |
|
| 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 |
|
| 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 |
|
| [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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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
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
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on
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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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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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6524
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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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SUB14453MIG
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DTXSID4020791
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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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ACTIVE MOIETY |
