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Identification
Name Malathion
Accession Number DB00772 (APRD01081)
Type small molecule
Groups approved
Description

A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Carbofos
Carbophos
Compound 4049
Experimental insecticide 4049
Insecticide no. 4049
Malathione
Maldison
Mercaptosuccinic acid diethyl ester
Mercaptothion
Mercaptotion
MLT
Oleophosphothion
First Prev Next Last
Salts Not Available
Brand names
Name Company
Calmathion
Carbethoxy malathion
Carbetovur
Carbetox
Celthion
Chemathion
Cimexan
Cleensheen
Cythion
Derbac-M
Detmol MA
Emmatos
Emmatos extra
Ethiolacar
Etiol
Extermathion
Fog 3
Formal
Forthion
Fosfothion
Fosfotion
Fosfotion 550
Fyfanon
Hilthion
Hilthion 25WDP
Karbofos
Kop-thion
Kop-Thionkypfosmalacide
Kypfos
Latka 4049
Lice Rid
Malacide
Malafor
Malagran
Malakill
Malamar
Malamar 50
Malaphele
Malaphos
Malasol
Malaspray
Malathion 60
Malathion E50
Malathion LV Concentrate
Malathiozoo
Malathon
Malation
Malatol
Malatox
Malmed
Malphos
Maltox
Maltox MLT
Moscarda
OMS 1
Organoderm
Ortho Malathion
Ovide
Phosphothion
Prioderm
Sadofos
Sadofos 30
Sadophos
Siptox I
Staeubol-Puder
Suleo-M
Sumitox
TAK
Taskil
Vegfru malatox
Vetiol
Zithiol
First Prev Next Last
Brand mixtures Not Available
Categories
  • Cholinesterase Inhibitors
  • Insecticides
CAS number 121-75-5
Weight Average: 330.358
Monoisotopic: 330.036066232
Chemical Formula C10H19O6PS2
InChI Key InChIKey=JXSJBGJIGXNWCI-UHFFFAOYSA-N
InChI
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
Plain Text
IUPAC Name
1,4-diethyl 2-{[dimethoxy(sulfanylidene)-$l^{5}-phosphanyl]sulfanyl}butanedioate
SMILES
CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC
Plain Text
Mass Spec show (10.5 KB)
Taxonomy
Kingdom Organic
Classes
  • Carboxylic Acids and Derivatives
  • Phosphoric Acids and Derivatives
  • Keto-Acids
Substructures
  • Carboxylic Acids and Derivatives
  • Acetates
  • Ethers
  • Phosphoric Acids and Derivatives
  • Keto-Acids
Pharmacology
Indication For patients infected with Pediculus humanus capitis (head lice and their ova) of the scalp hair.
Pharmacodynamics Malathion is an organophosphate insecticide commonly used to control mosquitos and other flying insects. Pharmaceutically, malathion is used to eliminate head lice. The principal toxicological effect of malathion is cholinesterase inhibition, due primarily to malaoxon and to phosphorus thionate impurities.
Mechanism of action Malathion is a nonsystemic, wide-spectrum organophosphate insecticide. It inhibits acetylcholinesterase activity of most eukaryotes. Malathion is toxic to aquatic organisms, but has a relatively low toxicity for birds and mammals. The major metabolites of malathion are mono- and di-carboxylic acid derivatives, and malaoxon is a minor metabolite. However, it is malaoxon that is the strongest cholinesterase inhibitor. Cholinesterases catalyze the hydrolysis of the neurotransmitter acetylcholine into choline and acetic acid, a reaction necessary to allow a cholinergic neuron to return to its resting state after activation. Because of its essential function, chemicals that interfere with the action of cholinesterase are potent neurotoxins, causing muscle spasms and ultimately death.
Absorption Malathion in an acetone vehicle has been reported to be absorbed through normal human skin only to the extent of 8% of the applied dose. Absorption may be increased when malathion is applied to damaged skin. Malathion is rapidly and effectively absorbed by practically all routes including the gastrointestinal tract, skin, mucous membranes, and lungs. However, it is readily excreted in the urine, and does not accumulate in organs or tissues.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
The major metabolites of malathion are the diacid and monoacid metabolites, namely, malathion dicarboxylic acid (DCA) and malathion monocarboxylic acid (MCA). Malaoxon, the active cholinesterase-inhibiting metabolite of malathion, is a minor metabolite. Both malathion and malaoxon are detoxified by carboxyesterases leading to polar, water-soluble compounds that are excreted.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Malathion
    		Malaoxon Details
    Malathion
      		Malathion dicarboxylic acid Details
      Malathion
        		Malathion monocarboxylic acid Details
        Route of elimination Not Available
        Half life 8-24 hours
        Clearance Not Available
        Toxicity Malathion is slightly toxic via the oral route, with reported oral LD50 values of 1000 mg/kg to greater than 10,000 mg/kg in the rat. It is also slightly toxic via the dermal route, with reported dermal LD50 values of greater than 4000 mg/kg in rats. Moderate poisoning can result in chest tightness, difficulty breathing, bradycardia, tachycardia, tremor/ataxia, blurred vision, and confusion. Severe, life-threatening signs include coma, seizures, respiratory arrest, and paralysis. Malathion may also be irritating to the skin and eyes.
        Affected organisms
        • Head lice
        Pathways Not Available
        Pharmacoeconomics
        Manufacturers
        • Synerx pharma llc
        • Taro pharmaceuticals north america inc
        Packagers
        Dosage forms
        Form Route Strength
        Lotion Topical
        Prices
        Unit description Cost Unit
        Ovide 0.5% Lotion 59ml Bottle 180.8 USD bottle
        Ovide 0.5% lotion 2.95 USD ml
        Malathion 0.5% lotion 2.65 USD ml
        DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
        Patents
        Country Patent Number Approved Expires (estimated)
        United States 7560445 2007-02-01 2027-02-01
        Properties
        State liquid
        Experimental Properties
        Property Value Source
        melting point 2.8 °C PhysProp
        boiling point 156-157 °C at 7.00E-01 mm Hg PhysProp
        water solubility 143 mg/L (at 20 °C) BOWMAN,BT & SANS,WW (1983)
        logP 2.36 HANSCH,C ET AL. (1995)
        Predicted Properties
        Property Value Source
        water solubility 1.65e-01 g/l ALOGPS
        logP 2.67 ALOGPS
        logP 1.86 ChemAxon
        logS -3.3 ALOGPS
        pKa (strongest basic) -6.8 ChemAxon
        physiological charge 0 ChemAxon
        hydrogen acceptor count 2 ChemAxon
        hydrogen donor count 0 ChemAxon
        polar surface area 71.06 ChemAxon
        rotatable bond count 11 ChemAxon
        refractivity 78.18 ChemAxon
        polarizability 31.66 ChemAxon
        References
        Synthesis Reference Not Available
        General Reference
        1. Baker EL Jr, Warren M, Zack M, Dobbin RD, Miles JW, Miller S, Alderman L, Teeters WR: Epidemic malathion poisoning in Pakistan malaria workers. Lancet. 1978 Jan 7;1(8054):31-4. Pubmed
        2. Bonner MR, Coble J, Blair A, Beane Freeman LE, Hoppin JA, Sandler DP, Alavanja MC: Malathion exposure and the incidence of cancer in the agricultural health study. Am J Epidemiol. 2007 Nov 1;166(9):1023-34. Epub 2007 Aug 23. Pubmed
        3. Edwards JW, Lee SG, Heath LM, Pisaniello DL: Worker exposure and a risk assessment of malathion and fenthion used in the control of Mediterranean fruit fly in South Australia. Environ Res. 2007 Jan;103(1):38-45. Epub 2006 Aug 17. Pubmed
        External Links
        Resource Link
        KEGG Drug D00534 Link_out
        KEGG Compound C07497 Link_out
        PubChem Compound 4004 Link_out
        PubChem Substance 46505287 Link_out
        ChemSpider 3864 Link_out
        BindingDB 50240924 Link_out
        ChEBI 6651 Link_out
        ChEMBL 6651 Link_out
        Therapeutic Targets Database DAP000895 Link_out
        PharmGKB PA164748092 Link_out
        RxList http://www.rxlist.com/cgi/generic3/ovide.htm Link_out
        Drugs.com http://www.drugs.com/cdi/malathion.html Link_out
        Wikipedia http://en.wikipedia.org/wiki/Malathion Link_out
        ATC Codes
        • P03AX03
        AHFS Codes Not Available
        PDB Entries Not Available
        FDA label show (133 KB)
        MSDS show (57.9 KB)
        Interactions
        Drug Interactions Searched, but no interactions found.
        Food Interactions Not Available
        Targets

        1. Cholinesterase

        Pharmacological action: yes
        Actions: inhibitor

        An acylcholine + H(2)O = choline + a carboxylate

        Organism class: human
        UniProt ID: P06276 Link_out
        Gene: BCHE Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        SNPs: SNPJam Report Link_out

        References:
        1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
        2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
        3. Ramos ZR, Fortunato JJ, Agostinho FR, Martins MR, Correa M, Schetinger MR, Dal-Pizzol F, Quevedo J: Influence of malathion on acetylcholinesterase activity in rats submitted to a forced swimming test. Neurotox Res. 2006 Jun;9(4):285-90. Pubmed
        4. Ahmed M, Rocha JB, Mazzanti CM, Morsch AL, Cargnelutti D, Correa M, Loro V, Morsch VM, Schetinger MR: Malathion, carbofuran and paraquat inhibit Bungarus sindanus (krait) venom acetylcholinesterase and human serum butyrylcholinesterase in vitro. Ecotoxicology. 2007 May;16(4):363-9. Epub 2007 Mar 16. Pubmed
        5. da Silva AP, Meotti FC, Santos AR, Farina M: Lactational exposure to malathion inhibits brain acetylcholinesterase in mice. Neurotoxicology. 2006 Dec;27(6):1101-5. Epub 2006 Apr 28. Pubmed
        6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed
        Enzymes

        1. Cytochrome P450 1A2

        Actions: substrate

        Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

        UniProt ID: P05177 Link_out
        Gene: CYP1A2
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        SNPs: SNPJam Report Link_out

        References:
        1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

        2. Cytochrome P450 2B6

        Actions: substrate

        Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

        UniProt ID: P20813 Link_out
        Gene: CYP2B6 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        SNPs: SNPJam Report Link_out

        References:
        1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
        Comments
        Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19