Identification

Name
Malathion
Accession Number
DB00772  (APRD01081)
Type
Small Molecule
Groups
Approved, Investigational
Description

Malathion is a parasympathomimetic organophosphate compound that is used as an insecticide for the treatment of head lice. Malathion is an irreversible cholinesterase inhibitor and has low human toxicity.

Structure
Thumb
Synonyms
  • [(dimethoxyphosphinothioyl)thio]butanedioic acid diethyl ester
  • Carbophos
  • diethyl (dimethoxyphosphinothioylthio)succinate
  • Karbofos
  • Maldison
  • Mercaptothion
  • O,O-dimethyl S-(1,2-bis(ethoxycarbonyl)ethyl)
  • O,O-dimethyl S-(1,2-dicarbethoxyethyl) dithiophosphate
  • O,O-dimethyl S-(1,2-dicarbethoxyethyl)phosphorodithioate
  • O,O-dimethyl S-1,2-di(ethoxycarbamyl)ethyl
  • O,O-dimethyldithiophosphate diethylmercaptosuccinate
External IDs
ENT 17,034 / ENT-17034 / NSC-6524
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MalathionLotion.005 g/mLTopicalTaro Pharmaceuticals U.S.A., Inc.2009-08-02Not applicableUs
OvideLotion.005 g/mLTopicalTaro Pharmaceuticals, Inc.1982-08-02Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MalathionLotion.005 g/mLTopicalSuven Life Sciences Limited2014-02-20Not applicableUs
MalathionLotion.0005 g/mLTopicalTaro Pharmaceuticals U.S.A., Inc.2014-01-31Not applicableUs
Malathion lotion, 0.5%Lotion5 mg/mLTopicalKaralex Pharma, Llc, Woodcliff Lake, Nj 076772009-05-13Not applicableUs
OvideLotion.0005 g/mLTopicalTaro Pharmaceuticals U.S.A., Inc.2014-01-31Not applicableUs
International/Other Brands
Derbac-M (SSL) / Noury (Alfaco) / Prioderm (Norpharma)
Categories
UNII
U5N7SU872W
CAS number
121-75-5
Weight
Average: 330.358
Monoisotopic: 330.036066232
Chemical Formula
C10H19O6PS2
InChI Key
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
IUPAC Name
1,4-diethyl 2-{[dimethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}butanedioate
SMILES
CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC

Pharmacology

Indication

For patients infected with Pediculus humanus capitis (head lice and their ova) of the scalp hair.

Structured Indications
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.

TargetActionsOrganism
ACholinesterase
inhibitor
Human
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.

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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when 16-Bromoepiandrosterone is combined with Malathion.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when 19-norandrostenedione is combined with Malathion.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when 5-androstenedione is combined with Malathion.Experimental, Illicit
AbirateroneThe serum concentration of Malathion can be increased when it is combined with Abiraterone.Approved
AcebutololMalathion may increase the bradycardic activities of Acebutolol.Approved
AcetylcholineThe risk or severity of adverse effects can be increased when Malathion is combined with Acetylcholine.Approved
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Malathion.Approved
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Malathion.Approved
AlcuroniumThe therapeutic efficacy of Alcuronium can be decreased when used in combination with Malathion.Experimental
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Malathion.Experimental
AlprenololMalathion may increase the bradycardic activities of Alprenolol.Approved, Withdrawn
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Malathion.Approved
AndrostenedioneThe risk or severity of adverse effects can be increased when Androstenedione is combined with Malathion.Experimental, Illicit
AnecortaveThe risk or severity of adverse effects can be increased when Anecortave is combined with Malathion.Investigational
anecortave acetateThe risk or severity of adverse effects can be increased when anecortave acetate is combined with Malathion.Investigational
Anisotropine MethylbromideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Malathion.Approved
ArecolineThe risk or severity of adverse effects can be increased when Malathion is combined with Arecoline.Experimental
ArotinololMalathion may increase the bradycardic activities of Arotinolol.Approved
AtamestaneThe risk or severity of adverse effects can be increased when Atamestane is combined with Malathion.Investigational
AtenololMalathion may increase the bradycardic activities of Atenolol.Approved
AtracuriumThe therapeutic efficacy of Atracurium can be decreased when used in combination with Malathion.Experimental
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be decreased when used in combination with Malathion.Approved
AtropineThe therapeutic efficacy of Atropine can be decreased when used in combination with Malathion.Approved, Vet Approved
AzithromycinThe metabolism of Malathion can be decreased when combined with Azithromycin.Approved
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Malathion.Approved, Investigational
BefunololMalathion may increase the bradycardic activities of Befunolol.Experimental
BenactyzineThe therapeutic efficacy of Benactyzine can be decreased when used in combination with Malathion.Withdrawn
BenzatropineThe therapeutic efficacy of Benzatropine can be decreased when used in combination with Malathion.Approved
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Malathion.Approved, Vet Approved
BetaxololMalathion may increase the bradycardic activities of Betaxolol.Approved
BethanecholThe risk or severity of adverse effects can be increased when Malathion is combined with Bethanechol.Approved
BevantololMalathion may increase the bradycardic activities of Bevantolol.Approved
BiperidenThe therapeutic efficacy of Biperiden can be decreased when used in combination with Malathion.Approved
BisoprololMalathion may increase the bradycardic activities of Bisoprolol.Approved
BopindololMalathion may increase the bradycardic activities of Bopindolol.Approved
BornaprineThe therapeutic efficacy of Bornaprine can be decreased when used in combination with Malathion.Experimental
BortezomibThe metabolism of Malathion can be decreased when combined with Bortezomib.Approved, Investigational
BucindololMalathion may increase the bradycardic activities of Bucindolol.Investigational
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Malathion.Approved
BufuralolMalathion may increase the bradycardic activities of Bufuralol.Experimental, Investigational
BupranololMalathion may increase the bradycardic activities of Bupranolol.Approved
CaffeineThe metabolism of Malathion can be decreased when combined with Caffeine.Approved
CarbacholThe risk or severity of adverse effects can be increased when Malathion is combined with Carbachol.Approved
CarbamazepineThe metabolism of Malathion can be increased when combined with Carbamazepine.Approved, Investigational
CarteololMalathion may increase the bradycardic activities of Carteolol.Approved
CarvedilolMalathion may increase the bradycardic activities of Carvedilol.Approved, Investigational
CeliprololMalathion may increase the bradycardic activities of Celiprolol.Approved, Investigational
CevimelineThe risk or severity of adverse effects can be increased when Malathion is combined with Cevimeline.Approved
ChlorphenoxamineThe therapeutic efficacy of Chlorphenoxamine can be decreased when used in combination with Malathion.Withdrawn
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Malathion.Approved, Investigational
CitalopramThe metabolism of Malathion can be decreased when combined with Citalopram.Approved
ClobetasolThe risk or severity of adverse effects can be increased when Clobetasol is combined with Malathion.Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Malathion.Approved
ClobetasoneThe risk or severity of adverse effects can be increased when Clobetasone is combined with Malathion.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Malathion.Approved
ClopidogrelThe metabolism of Malathion can be decreased when combined with Clopidogrel.Approved, Nutraceutical
CloranololMalathion may increase the bradycardic activities of Cloranolol.Experimental
ClotrimazoleThe metabolism of Malathion can be decreased when combined with Clotrimazole.Approved, Vet Approved
Cortexolone 17α-propionateThe risk or severity of adverse effects can be increased when Cortexolone 17α-propionate is combined with Malathion.Investigational
CorticosteroneThe risk or severity of adverse effects can be increased when Corticosterone is combined with Malathion.Experimental
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Malathion.Approved
CrizotinibThe metabolism of Malathion can be decreased when combined with Crizotinib.Approved
CyclopentolateThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Malathion.Approved
Cyproterone acetateThe serum concentration of Malathion can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Malathion can be decreased when it is combined with Dabrafenib.Approved
DarifenacinThe therapeutic efficacy of Darifenacin can be decreased when used in combination with Malathion.Approved, Investigational
DeferasiroxThe serum concentration of Malathion can be increased when it is combined with Deferasirox.Approved, Investigational
DesipramineThe metabolism of Malathion can be decreased when combined with Desipramine.Approved
DesloratadineThe therapeutic efficacy of Desloratadine can be decreased when used in combination with Malathion.Approved, Investigational
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Malathion.Approved
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Malathion.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with Malathion.Experimental, Vet Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Malathion.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Malathion.Vet Approved
DexetimideThe therapeutic efficacy of Dexetimide can be decreased when used in combination with Malathion.Withdrawn
DicyclomineThe therapeutic efficacy of Dicyclomine can be decreased when used in combination with Malathion.Approved
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Malathion.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Malathion.Approved
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Malathion.Approved
DipyridamoleThe therapeutic efficacy of Malathion can be decreased when used in combination with Dipyridamole.Approved
DosulepinThe metabolism of Malathion can be decreased when combined with Dosulepin.Approved
DoxorubicinThe metabolism of Malathion can be decreased when combined with Doxorubicin.Approved, Investigational
EmeproniumThe therapeutic efficacy of Emepronium can be decreased when used in combination with Malathion.Experimental
EpanololMalathion may increase the bradycardic activities of Epanolol.Experimental
EpibatidineThe risk or severity of adverse effects can be increased when Malathion is combined with Epibatidine.Experimental
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Malathion.Experimental
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Malathion.Approved
EsmololMalathion may increase the bradycardic activities of Esmolol.Approved
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Malathion.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Estrone sulfate is combined with Malathion.Approved
EtanautineThe therapeutic efficacy of Etanautine can be decreased when used in combination with Malathion.Experimental
EthopropazineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Malathion.Approved
EtybenzatropineThe therapeutic efficacy of Etybenzatropine can be decreased when used in combination with Malathion.Experimental
FesoterodineThe therapeutic efficacy of Fesoterodine can be decreased when used in combination with Malathion.Approved
fluasteroneThe risk or severity of adverse effects can be increased when fluasterone is combined with Malathion.Investigational
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Malathion.Approved
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Malathion.Approved, Vet Approved
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Malathion.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Malathion.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Malathion.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Malathion.Approved
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Malathion.Approved, Withdrawn
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Malathion.Approved
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Malathion.Approved
FluvoxamineThe metabolism of Malathion can be decreased when combined with Fluvoxamine.Approved, Investigational
FormestaneThe risk or severity of adverse effects can be increased when Formestane is combined with Malathion.Approved, Investigational, Withdrawn
FosphenytoinThe metabolism of Malathion can be increased when combined with Fosphenytoin.Approved
GallamineThe therapeutic efficacy of Gallamine can be decreased when used in combination with Malathion.Experimental
Gallamine TriethiodideThe therapeutic efficacy of Gallamine Triethiodide can be decreased when used in combination with Malathion.Approved
GlycopyrroniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Malathion.Approved, Investigational, Vet Approved
GTS-21The risk or severity of adverse effects can be increased when Malathion is combined with GTS-21.Investigational
HE3286The risk or severity of adverse effects can be increased when HE3286 is combined with Malathion.Investigational
HexamethoniumThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Malathion.Experimental
HomatropineThe therapeutic efficacy of Homatropine can be decreased when used in combination with Malathion.Approved
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Malathion.Approved, Vet Approved
HyoscyamineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Malathion.Approved
IndenololMalathion may increase the bradycardic activities of Indenolol.Withdrawn
Ipratropium bromideThe therapeutic efficacy of Ipratropium bromide can be decreased when used in combination with Malathion.Approved
IstaroximeThe risk or severity of adverse effects can be increased when Istaroxime is combined with Malathion.Investigational
LabetalolMalathion may increase the bradycardic activities of Labetalol.Approved
LandiololMalathion may increase the bradycardic activities of Landiolol.Investigational
LevobunololMalathion may increase the bradycardic activities of Levobunolol.Approved
LidocaineThe metabolism of Malathion can be decreased when combined with Lidocaine.Approved, Vet Approved
LobeglitazoneThe metabolism of Malathion can be decreased when combined with Lobeglitazone.Approved
LobelineThe risk or severity of adverse effects can be increased when Malathion is combined with Lobeline.Investigational
LumacaftorThe serum concentration of Malathion can be decreased when it is combined with Lumacaftor.Approved
MazaticolThe therapeutic efficacy of Mazaticol can be decreased when used in combination with Malathion.Experimental
ME-609The risk or severity of adverse effects can be increased when ME-609 is combined with Malathion.Investigational
MecamylamineThe therapeutic efficacy of Mecamylamine can be decreased when used in combination with Malathion.Approved
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Malathion.Approved
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Malathion.Vet Approved
MepindololMalathion may increase the bradycardic activities of Mepindolol.Experimental
MethacholineThe risk or severity of adverse effects can be increased when Malathion is combined with Methacholine.Approved
MethanthelineThe therapeutic efficacy of Methantheline can be decreased when used in combination with Malathion.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Malathion.Approved, Vet Approved
MetipranololMalathion may increase the bradycardic activities of Metipranolol.Approved
MetixeneThe therapeutic efficacy of Metixene can be decreased when used in combination with Malathion.Approved
MetoprololMalathion may increase the bradycardic activities of Metoprolol.Approved, Investigational
MexiletineThe metabolism of Malathion can be decreased when combined with Mexiletine.Approved
MidostaurinThe metabolism of Malathion can be decreased when combined with Midostaurin.Approved
MivacuriumMalathion may decrease the neuromuscular blocking activities of Mivacurium.Approved
NadololMalathion may increase the bradycardic activities of Nadolol.Approved
NCX 1022The risk or severity of adverse effects can be increased when NCX 1022 is combined with Malathion.Investigational
NevirapineThe metabolism of Malathion can be increased when combined with Nevirapine.Approved
NicotineThe risk or severity of adverse effects can be increased when Malathion is combined with Nicotine.Approved
Oleoyl-estroneThe risk or severity of adverse effects can be increased when Oleoyl-estrone is combined with Malathion.Investigational
OrphenadrineThe therapeutic efficacy of Orphenadrine can be decreased when used in combination with Malathion.Approved
OsimertinibThe serum concentration of Malathion can be decreased when it is combined with Osimertinib.Approved
OtiloniumThe therapeutic efficacy of Otilonium can be decreased when used in combination with Malathion.Experimental
OxitropiumThe therapeutic efficacy of Oxitropium can be decreased when used in combination with Malathion.Investigational
OxprenololMalathion may increase the bradycardic activities of Oxprenolol.Approved
OxybutyninThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with Malathion.Approved, Investigational
OxyphenoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Malathion.Approved
PancuroniumThe therapeutic efficacy of Pancuronium can be decreased when used in combination with Malathion.Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Malathion.Approved
ParoxetineThe metabolism of Malathion can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Malathion can be increased when it is combined with Peginterferon alfa-2b.Approved
PenbutololMalathion may increase the bradycardic activities of Penbutolol.Approved, Investigational
PentoliniumThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Malathion.Approved
PhenglutarimideThe therapeutic efficacy of Phenglutarimide can be decreased when used in combination with Malathion.Experimental
PhenobarbitalThe metabolism of Malathion can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Malathion can be increased when combined with Phenytoin.Approved, Vet Approved
PilocarpineThe risk or severity of adverse effects can be increased when Malathion is combined with Pilocarpine.Approved
PindololMalathion may increase the bradycardic activities of Pindolol.Approved
PipecuroniumThe therapeutic efficacy of Pipecuronium can be decreased when used in combination with Malathion.Approved
PirenzepineThe therapeutic efficacy of Pirenzepine can be decreased when used in combination with Malathion.Approved
PractololMalathion may increase the bradycardic activities of Practolol.Approved
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Malathion.Approved, Nutraceutical
Prasterone sulfateThe risk or severity of adverse effects can be increased when Prasterone sulfate is combined with Malathion.Investigational
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Malathion.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Malathion.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Malathion.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Malathion.Experimental
PrimidoneThe metabolism of Malathion can be increased when combined with Primidone.Approved, Vet Approved
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Malathion.Approved
PropanthelineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Malathion.Approved
PropiverineThe therapeutic efficacy of Propiverine can be decreased when used in combination with Malathion.Investigational
PropranololMalathion may increase the bradycardic activities of Propranolol.Approved, Investigational
QuazepamThe serum concentration of Malathion can be increased when it is combined with Quazepam.Approved, Illicit
QuinidineThe therapeutic efficacy of Quinidine can be decreased when used in combination with Malathion.Approved
RapacuroniumMalathion may decrease the neuromuscular blocking activities of Rapacuronium.Withdrawn
RifampicinThe metabolism of Malathion can be increased when combined with Rifampicin.Approved
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Malathion.Approved
RopiniroleThe metabolism of Malathion can be decreased when combined with Ropinirole.Approved, Investigational
ScopolamineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with Malathion.Approved
Scopolamine butylbromideThe therapeutic efficacy of Scopolamine butylbromide can be decreased when used in combination with Malathion.Approved, Vet Approved
SertralineThe metabolism of Malathion can be decreased when combined with Sertraline.Approved
SimeprevirThe metabolism of Malathion can be decreased when combined with Simeprevir.Approved
SolifenacinThe therapeutic efficacy of Solifenacin can be decreased when used in combination with Malathion.Approved
SorafenibThe metabolism of Malathion can be decreased when combined with Sorafenib.Approved, Investigational
SotalolMalathion may increase the bradycardic activities of Sotalol.Approved
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Malathion.Approved
TalinololMalathion may increase the bradycardic activities of Talinolol.Investigational
Tenofovir disoproxilThe metabolism of Malathion can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TeriflunomideThe serum concentration of Malathion can be decreased when it is combined with Teriflunomide.Approved
TertatololMalathion may increase the bradycardic activities of Tertatolol.Experimental
TheophyllineThe metabolism of Malathion can be decreased when combined with Theophylline.Approved
ThiotepaThe metabolism of Malathion can be decreased when combined with Thiotepa.Approved
TiclopidineThe metabolism of Malathion can be decreased when combined with Ticlopidine.Approved
TimololMalathion may increase the bradycardic activities of Timolol.Approved
TiotropiumThe therapeutic efficacy of Tiotropium can be decreased when used in combination with Malathion.Approved
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Malathion.Approved
TolterodineThe therapeutic efficacy of Tolterodine can be decreased when used in combination with Malathion.Approved, Investigational
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Malathion.Approved, Vet Approved
TrihexyphenidylThe therapeutic efficacy of Trihexyphenidyl can be decreased when used in combination with Malathion.Approved
TrimethaphanThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Malathion.Approved
TropatepineThe therapeutic efficacy of Tropatepine can be decreased when used in combination with Malathion.Experimental
TropicamideThe therapeutic efficacy of Tropicamide can be decreased when used in combination with Malathion.Approved
TrospiumThe therapeutic efficacy of Trospium can be decreased when used in combination with Malathion.Approved
TubocurarineThe therapeutic efficacy of Tubocurarine can be decreased when used in combination with Malathion.Approved
VareniclineThe risk or severity of adverse effects can be increased when Malathion is combined with Varenicline.Approved, Investigational
VecuroniumThe therapeutic efficacy of Vecuronium can be decreased when used in combination with Malathion.Approved
VemurafenibThe serum concentration of Malathion can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Malathion can be decreased when combined with Venlafaxine.Approved
ZucapsaicinThe metabolism of Malathion can be decreased when combined with Zucapsaicin.Approved
Food Interactions
Not Available

References

Synthesis Reference

Noel Rouy, Georges Gros, "Process for the preparation of malathion." U.S. Patent US4367180, issued August, 1969.

US4367180
General References
  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:74508]
  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:17720683]
  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:16914134]
External Links
Human Metabolome Database
HMDB14910
KEGG Drug
D00534
KEGG Compound
C07497
PubChem Compound
4004
PubChem Substance
46505287
ChemSpider
3864
BindingDB
85372
ChEBI
6651
ChEMBL
CHEMBL1200468
Therapeutic Targets Database
DAP000895
PharmGKB
PA164748092
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Malathion
ATC Codes
P03AX03 — Malathion
FDA label
Download (133 KB)
MSDS
Download (57.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentLice Infestations1
2CompletedTreatmentLice of the head1
2, 3CompletedTreatmentLice Infestations1
3CompletedTreatmentLice Infestations3

Pharmacoeconomics

Manufacturers
  • Synerx pharma llc
  • Taro pharmaceuticals north america inc
Packagers
Dosage forms
FormRouteStrength
LotionTopical5 mg/mL
LotionTopical.0005 g/mL
LotionTopical.005 g/mL
Prices
Unit descriptionCostUnit
Ovide 0.5% Lotion 59ml Bottle180.8USD bottle
Ovide 0.5% lotion2.95USD ml
Malathion 0.5% lotion2.65USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7560445No2007-02-012027-02-01Us
US7977324No2006-08-142026-08-14Us

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)2.8 °CPhysProp
boiling point (°C)156-157 °C at 7.00E-01 mm HgPhysProp
water solubility143 mg/L (at 20 °C)BOWMAN,BT & SANS,WW (1983)
logP2.36HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.165 mg/mLALOGPS
logP2.67ALOGPS
logP1.86ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area71.06 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity78.18 m3·mol-1ChemAxon
Polarizability31.66 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9031
Blood Brain Barrier+0.9236
Caco-2 permeable-0.5579
P-glycoprotein substrateNon-substrate0.7901
P-glycoprotein inhibitor INon-inhibitor0.6817
P-glycoprotein inhibitor IINon-inhibitor0.9522
Renal organic cation transporterNon-inhibitor0.9414
CYP450 2C9 substrateNon-substrate0.8308
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6132
CYP450 1A2 substrateNon-inhibitor0.8415
CYP450 2C9 inhibitorNon-inhibitor0.7963
CYP450 2D6 inhibitorNon-inhibitor0.9114
CYP450 2C19 inhibitorNon-inhibitor0.748
CYP450 3A4 inhibitorNon-inhibitor0.5673
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8504
Ames testNon AMES toxic0.9132
CarcinogenicityCarcinogens 0.6261
BiodegradationNot ready biodegradable0.8429
Rat acute toxicity3.0259 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9228
hERG inhibition (predictor II)Non-inhibitor0.8641
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.5 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-004i-8900000000-c6bc16fae6e217410d40
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acid esters
Direct Parent
Fatty acid esters
Alternative Parents
Dithiophosphate S-esters / Dithiophosphate O-esters / Dicarboxylic acids and derivatives / Carboxylic acid esters / Sulfenyl compounds / Organothiophosphorus compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Fatty acid ester / Dicarboxylic acid or derivatives / Dithiophosphate o-ester / Dithiophosphate s-ester / Organic dithiophosphate / Carboxylic acid ester / Carboxylic acid derivative / Organothiophosphorus compound / Sulfenyl compound / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
ethyl ester, diester, organic thiophosphate, carboxyalkyl phosphate (CHEBI:6651) / Organophosphorus insecticides (C07497) / a small molecule (CPD-13116)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
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:17139284]
  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:17016423]
  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:16782587]
  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:17364237]
  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:16716398]
  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:10592235]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
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 un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:45