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

Details

Stereochemistry RACEMIC
Molecular Formula C10H19O7PS
Molecular Weight 314.292
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MALAOXON

SMILES

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

InChI

InChIKey=WSORODGWGUUOBO-UHFFFAOYSA-N
InChI=1S/C10H19O7PS/c1-5-16-9(11)7-8(10(12)17-6-2)19-18(13,14-3)15-4/h8H,5-7H2,1-4H3

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
Metabolism of organophosphorus insecticides. XIV. Malathion breakdown by soil fungi.
1972 Sep
Interaction of dichlorvos and anticholinesterases on the in vitro inhibition of human blood cholinesterases.
1974 Feb
DDVP (dichlorvos) detoxification by binding and interactions with DDT, dieldrin, and malaoxon.
1977 Oct
Time-course of malaoxon-induced alterations in brain regional inositol-1-phosphate levels in convulsing and nonconvulsing rats.
1989 Feb
Potentiation of malaoxon-induced convulsions by lithium: early neuronal injury, phosphoinositide signaling, and calcium.
1990 Jun 15
Malaoxon-induced brain phosphoinositide turnover and changes in brain calcium levels by female gender in pregnant and non-pregnant convulsing and non-convulsing rats.
1993 Nov
Resistance-associated point mutations in insecticide-insensitive acetylcholinesterase.
1994 Jun 21
Reactivation by various oximes of human erythrocyte acetylcholinesterase inhibited by different organophosphorus compounds.
1996
Acetylcholinesterase and neuropathy target esterase inhibitions in neuroblastoma cells to distinguish organophosphorus compounds causing acute and delayed neurotoxicity.
1997 Jul
Inhibition of carboxylesterases in SH-SY5Y human and NB41A3 mouse neuroblastoma cells by organophosphorus esters.
1998 Mar 13
Life without acetylcholinesterase: the implications of cholinesterase inhibitor toxicity in AChE-knockout mice.
2005 May
Assessment of attractiveness of plants as roosting sites for the melon fly, Bactrocera cucurbitae, and oriental fruit fly, Bactrocera dorsalis.
2007
Inhibition of AChE by single and simultaneous exposure to malathion and its degradation products.
2007 Dec
Resistance to malathion in field populations of Ceratitis capitata.
2007 Dec
Mechanisms of resistance to malathion in the medfly Ceratitis capitata.
2008 Aug
Inhibition of AChE by malathion and some structurally similar compounds.
2008 Aug
Comparing the relative toxicity of malathion and malaoxon in blue catfish Ictalurus furcatus.
2008 Aug
Determination of low-level pesticide residues in soft drinks and sports drinks by liquid chromatography with tandem mass spectrometry: collaborative study.
2008 Jan-Feb
Dermal absorption of a dilute aqueous solution of malathion.
2008 Jul
Albumin binding as a potential biomarker of exposure to moderately low levels of organophosphorus pesticides.
2008 Jun
Acute toxicity and tissue distributions of malathion in Ambystoma tigrinum.
2008 Oct
Increased organophosphate scavenging in a butyrylcholinesterase mutant.
2008 Sep 25
Paraoxonase 1 (PON1) modulates the toxicity of mixed organophosphorus compounds.
2009 Apr 15
Cholinesterase based amperometric biosensors for assay of anticholinergic compounds.
2009 Jun
A study of the degradation of organophosphorus pesticides in river waters and the identification of their degradation products by chromatography coupled with mass spectrometry.
2009 May
Mechanisms of organophosphate resistance in a field population of oriental migratory locust, Locusta migratoria manilensis (Meyen).
2009 May
Recombinant expression and biochemical characterization of the catalytic domain of acetylcholinesterase-1 from the African malaria mosquito, Anopheles gambiae.
2009 Sep
Selectivity of pesticides used in integrated apple production to the lacewing, Chrysoperla externa.
2010
Physiological and histopathological investigations on the effects of alpha-lipoic acid in rats exposed to malathion.
2010
The toxicity of mixtures of specific organophosphate compounds is modulated by paraoxonase 1 status.
2010
Behavioral and morphological endpoints: as an early response to sublethal malathion intoxication in the freshwater fish, Labeo rohita.
2010 Apr
Heterogeneous ozonation of suspended malathion and chlorpyrifos particles.
2010 Apr
Comparison of two blood-brain barrier in vitro systems: cytotoxicity and transfer assessments of malathion/oxon and lead acetate.
2010 Apr
Baculovirus expression, biochemical characterization and organophosphate sensitivity of rBmAChE1, rBmAChE2, and rBmAChE3 of Rhipicephalus (Boophilus) microplus.
2010 Aug 27
Down-regulated transcriptional level of Ace1 combined with mutations in Ace1 and Ace2 of Aphis gossypii are related with omethoate resistance.
2010 Dec 5
Measurement of acetylcholinesterase inhibition using bienzymes immobilized monolith micro-reactor with integrated electrochemical detection.
2010 Feb 5
Mass spectrometric analyses of organophosphate insecticide oxon protein adducts.
2010 Jan
Degradation behavior and products of malathion and chlorpyrifos spiked in apple juice by ultrasonic treatment.
2010 Jan
Heterologous expression, purification, and biochemical characterization of a greenbug (Schizaphis graminum) acetylcholinesterase encoded by a paralogous gene (ace-1).
2010 Jan-Feb
Investigation of in vitro effects of ethephon and chlorpyrifos, either alone or in combination, on rat intestinal muscle contraction.
2010 Mar
Evaluation of a modified QuEChERS method for the extraction of pesticides from agricultural, ornamental and forestal soils.
2010 Mar
Activity levels of B-esterases in the tadpoles of 11 species of frogs in the middle Paraná River floodplain: implication for ecological risk assessment of soybean crops.
2010 Oct
[Rapid simultaneous determination of organophosphorus pesticides in human serum and urine by liquid chromatography-mass spectrometry].
2010 Sep
In vitro reactivating effects of standard and newly developed oximes on malaoxon-inhibited mouse brain acetylcholinesterase.
2010 Sep
In vitro kinetic interactions of DEET, pyridostigmine and organophosphorus pesticides with human cholinesterases.
2011 Apr 25
Polymorphism in the acetylcholinesterase gene of Musca domestica L. field populations in Turkey.
2011 Dec
Assessments of tight junction proteins occludin, claudin 5 and scaffold proteins ZO1 and ZO2 in endothelial cells of the rat blood-brain barrier: cellular responses to neurotoxicants malathion and lead acetate.
2011 Jan
Esterase metabolism of cholinesterase inhibitors using rat liver in vitro.
2011 Mar 15
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.
2011 Mar 28
Malathion/oxon and lead acetate increase gene expression and protein levels of transient receptor potential canonical channel subunits TRPC1 and TRPC4 in rat endothelial cells of the blood-brain barrier.
2012 Jun
Patents

Patents

Name Type Language
MALAOXON
Common Name English
MALATHION OXYGEN ANALOG
Common Name English
MALATHION OXON
Common Name English
MALATHION IMPURITY B [EP IMPURITY]
Common Name English
OXYCARBOPHOS
Common Name English
MALAOXAN
Common Name English
SUCCINIC ACID, MERCAPTO-, DIETHYL ESTER, DIMETHYL PHOSPHATE
Systematic Name English
O,O-DIMETHYL S-1,2-BIS(ETHOXYCARBONYL)ETHYL PHOSPHOROTHIOATE
Common Name English
BUTANEDIOIC ACID, 2-((DIMETHOXYPHOSPHINYL)THIO)-, 1,4-DIETHYL ESTER
Systematic Name English
MALAOXONE
Common Name English
MALATHION-O-ANALOG
Common Name English
MALOXON
Common Name English
DL-MALAOXON
Common Name English
DIETHYL MERCAPTOSUCCINATE S-ESTER WITH O,O-DIMETHYL PHOSPHOROTHIOATE
Common Name English
BUTANEDIOIC ACID, ((DIMETHOXYPHOSPHINYL)THIO)-, DIETHYL ESTER
Systematic Name English
DIETHYL ((DIMETHOXYPHOSPHINO)THIO)BUTANEDIOATE
Systematic Name English
LIROMAT
Brand Name English
SUCCINIC ACID, MERCAPTO-, DIETHYL ESTER, S-ESTER WITH O,O-DIMETHYL PHOSPHOROTHIOATE
Systematic Name English
PHOSPHOROTHIOIC ACID, O,O-DIMETHYL ESTER, S-ESTER WITH DIETHYL MERCAPTOSUCCINATE
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 657701
Created by admin on Sat Dec 16 08:36:59 GMT 2023 , Edited by admin on Sat Dec 16 08:36:59 GMT 2023
Code System Code Type Description
CAS
1634-78-2
Created by admin on Sat Dec 16 08:36:59 GMT 2023 , Edited by admin on Sat Dec 16 08:36:59 GMT 2023
PRIMARY
DAILYMED
2439JYF84Q
Created by admin on Sat Dec 16 08:36:59 GMT 2023 , Edited by admin on Sat Dec 16 08:36:59 GMT 2023
PRIMARY
WIKIPEDIA
Malaoxon
Created by admin on Sat Dec 16 08:36:59 GMT 2023 , Edited by admin on Sat Dec 16 08:36:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID9020790
Created by admin on Sat Dec 16 08:36:59 GMT 2023 , Edited by admin on Sat Dec 16 08:36:59 GMT 2023
PRIMARY
PUBCHEM
15415
Created by admin on Sat Dec 16 08:36:59 GMT 2023 , Edited by admin on Sat Dec 16 08:36:59 GMT 2023
PRIMARY
HSDB
4047
Created by admin on Sat Dec 16 08:36:59 GMT 2023 , Edited by admin on Sat Dec 16 08:36:59 GMT 2023
PRIMARY
FDA UNII
2439JYF84Q
Created by admin on Sat Dec 16 08:36:59 GMT 2023 , Edited by admin on Sat Dec 16 08:36:59 GMT 2023
PRIMARY
CHEBI
6649
Created by admin on Sat Dec 16 08:36:59 GMT 2023 , Edited by admin on Sat Dec 16 08:36:59 GMT 2023
PRIMARY