MALATHION

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018613s017lbl.pdf

Malathion is an organophosphate insecticide, an inhibitor of cholinesterase. In low doses (0.5%) malathion is used for treatment of pediculosis and scabies.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 207 Target ID: CHEMBL2362988 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22286807	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pediculosis 9 Sources: https://www.drugs.com/pro/malathion.html	Curative		Approved 8429	OVIDE Approved Use Malathion lotion is indicated for patients infected with Pediculus humanus capitis (head lice and their ova) of the scalp hair. Launch Date 1982
Scabies 9 Sources: http://www.netdoctor.co.uk/medicines/skin-and-hair/a6535/derbac-m-liquid-malathion/	Curative		Approved 8429	DERBAC M Approved Use Malathion is used for topical treatment of scabies, usually as an aqueous lotion.

T_1/2

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: https://www.epa.gov/sites/production/files/2017-01/documents/ache_white_paper_for_hsrb_122016.pdf	healthy, 18-50 years n = 34 Health Status: healthy Age Group: 18-50 years Sex: M+F Population Size: 34 Sources: https://www.epa.gov/sites/production/files/2017-01/documents/ache_white_paper_for_hsrb_122016.pdf	Sources: https://www.epa.gov/sites/production/files/2017-01/documents/ache_white_paper_for_hsrb_122016.pdf
1.8 g single, intravenous Dose: 1.8 g Route: intravenous Route: single Dose: 1.8 g Sources: https://pubmed.ncbi.nlm.nih.gov/3612901	healthy, 24 years n = 1 Health Status: healthy Age Group: 24 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/3612901	DLT: Headache, Nausea... Dose limiting toxicities: Headache Nausea Urination abnormal NOS Sources: https://pubmed.ncbi.nlm.nih.gov/3612901
85 mg/m3 single, respiratory Highest studied dose Dose: 85 mg/m3 Route: respiratory Route: single Dose: 85 mg/m3 Sources: https://www.fs.fed.us/foresthealth/pesticide/pdfs/0520202c_Malathion.pdf Page: p. 24	healthy Health Status: healthy Sources: https://www.fs.fed.us/foresthealth/pesticide/pdfs/0520202c_Malathion.pdf Page: p. 24	Sources: https://www.fs.fed.us/foresthealth/pesticide/pdfs/0520202c_Malathion.pdf Page: p. 24
1000 mg/kg single, oral Lethal dose Dose: 1000 mg/kg Route: oral Route: single Dose: 1000 mg/kg Sources: https://www.fs.fed.us/foresthealth/pesticide/pdfs/0520202c_Malathion.pdf Page: p.20	healthy Health Status: healthy Sources: https://www.fs.fed.us/foresthealth/pesticide/pdfs/0520202c_Malathion.pdf Page: p.20	DLT: Death... Dose limiting toxicities: Death Sources: https://www.fs.fed.us/foresthealth/pesticide/pdfs/0520202c_Malathion.pdf 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: https://pubmed.ncbi.nlm.nih.gov/3612901	healthy, 24 years n = 1 Health Status: healthy Age Group: 24 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/3612901
Nausea	DLT	1.8 g single, intravenous Dose: 1.8 g Route: intravenous Route: single Dose: 1.8 g Sources: https://pubmed.ncbi.nlm.nih.gov/3612901	healthy, 24 years n = 1 Health Status: healthy Age Group: 24 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/3612901
Urination abnormal NOS	DLT	1.8 g single, intravenous Dose: 1.8 g Route: intravenous Route: single Dose: 1.8 g Sources: https://pubmed.ncbi.nlm.nih.gov/3612901	healthy, 24 years n = 1 Health Status: healthy Age Group: 24 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/3612901
Death	DLT	1000 mg/kg single, oral Lethal dose Dose: 1000 mg/kg Route: oral Route: single Dose: 1000 mg/kg Sources: https://www.fs.fed.us/foresthealth/pesticide/pdfs/0520202c_Malathion.pdf Page: p.20	healthy Health Status: healthy Sources: https://www.fs.fed.us/foresthealth/pesticide/pdfs/0520202c_Malathion.pdf Page: p.20

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	inhibitor 1767

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 599	CYP1A2 1054 CYP2B6 664 P-gp 1537 carboxylesterase 4	CYP1A1 108

Drug as perpetrator

Target	Modality	Activity
CYP1A1 218	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/20654334/	no
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/20183062/	strong [IC50 2.5 uM]
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21561794/	yes [IC50 114.2 uM]

Drug as victim

Target	Modality	Activity
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27774651/	no
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20183062/	yes
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20183062/	yes
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20183062/	yes
carboxylesterase 4	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/18613s009s010_ovide.pdf Page: 16.0	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-2211	http://www.3bsc.com/index/pro_info.php?id=70763
AA Blocks	AA009NX0	https://www.aablocks.com/goods/Goods/detail?id=AA009NX0
AHH Chemical co.,ltd	MT-53410	http://www.ahhchemical.com/product/MT-53410.html
AK Scientific, Inc. (AKSCI)	J10314	http://www.aksci.com/item_detail.php?cat=J10314
AK Scientific, Inc. (AKSCI)	R319	http://www.aksci.com/item_detail.php?cat=R319
AbMole Bioscience	M5760	http://www.abmole.com/products/malathion.html
Achemica	ACMC-20n0ay	http://www.achemica.com/prodinfo/?id=227917
Achemtek	1ST20168	http://achemtek.com/121-75-5-5
Achemtek	0104-021283	http://www.achemtek.com/121-75-5
Angene	AGN-PC-07A21X	http://www.angenechemical.com/productshow/AGN-PC-07A21X.html
Aurora Fine Chemicals LLC	A17.894.697	http://online.aurorafinechemicals.com/info?ID=A17.894.697
Aurum Pharmatech LLC	K-1631	http://www.Aurumpharmatech.com/Product/ProductDetails/K_1631
Avantor Inc	100201-486	https://us.vwr.com/store/catalog/product.jsp?catalog_number=100201-486
Avantor Inc	100573-634	https://us.vwr.com/store/catalog/product.jsp?catalog_number=100573-634
Avantor Inc	101095-370	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101095-370
Avantor Inc	76196-246	https://us.vwr.com/store/product/23882803/malathion-1-2-bis-ethoxycarbonyl-ethyl-o-o-dimethyl-phosphorodithioate-96-yellow-liquid
BioSynth	J-004630	https://www.biosynth.com/en/products/all-products/products/J-004630.html
Boerchem	BC203973	http://www.boerchem.com/?product_34271.html
Chem Scene	CS-4416	http://www.chemscene.com/121-75-5.html
ChemMol	44001648	http://www.chemmol.com/chemmol/44001648.html
ChemMol	49415632	http://www.chemmol.com/chemmol/49415632.html
Chemspace	CSSB00000038524	https://chem-space.com/CSSB00000038524
Clearsynth	CS-O-03439	http://www.clearsynth.com/en/CSO03439.html
Clearsynth	CS-EB-01254	https://www.clearsynth.com/en/CSEB01254.html
Clearsynth	CS-ER-01252	https://www.clearsynth.com/en/CSER01252.html
Debye Scientific	DB-041629	http://www.debyesci.com/cas_121-75-5.html
Finetech	FT-0701077	http://www.finetechnology-ind.com/prod/detail/pub/347841-48-9.html
Glentham Life Sciences	GK1583	http://www.glentham.com/products/product/GK1583/
LGC Standards	DRE-A14710000TO-1000	https://www.lgcstandards.com/US/en/p/DRE-A14710000TO-1000
LGC Standards	DRE-C14710000	https://www.lgcstandards.com/US/en/p/DRE-C14710000
LGC Standards	DRE-CR14710000	https://www.lgcstandards.com/US/en/p/DRE-CR14710000
LGC Standards	DRE-L14710000CY	https://www.lgcstandards.com/US/en/p/DRE-L14710000CY
LGC Standards	DRE-XA14710000CY	https://www.lgcstandards.com/US/en/p/DRE-XA14710000CY
MedChem Express	HY-B0943	https://www.medchemexpress.com/Malathion.html
MolPort	MolPort-003-665-439	https://www.molport.com/shop/molecule-link/MolPort-003-665-439
MuseChem	I000828	https://www.musechem.com/product/I000828.html
OChem	2921	http://www.ocheminc.com/index.php?act=psearch&pid=121M755
Sigma-Aldrich	31558_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/31558?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	36143_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/36143?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	91481_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/91481?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	M0120000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/m0120000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1374408_USP	https://www.sigmaaldrich.com/catalog/product/usp/1374408?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S534425	http://www.smolecule.com/products/s534425
THE BioTek	bt-274850	https://www.thebiotek.com/product/inhibitors/bt-274850
Yuhao Chemical	RT19782	http://www.chemyuhao.com/121-75-5.html
abcr GmbH	AB506770	http://www.abcr.de/shop/en/AB506770
iChemical	EBD2199090	http://www.ichemical.com/products/121-75-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Comparative sensitivity of embryo-larval toxicity assays with African catfish (Clarias gariepinus) and zebra fish (Danio rerio).	2001	11769256
Concentrations of pesticide residues in tissues of fish from Kolleru Lake in India.	2001	11769254
Organ procurement and successful transplantation after malathion poisoning.	2001	11762673
Malathion resistance and prevalence of the malathion carboxylesterase mechanism in populations of mosquito vectors of disease in Sri Lanka.	2001	11731814
Comparative residual toxicities of pesticides to the predator Agistemus industani (Acari: Stigmaeidae) on citrus in Florida.	2001	11697784
Interventions for treating headlice.	2001	11686980
Highly-substrate active isoenzyme acetylcholinesterase-II, in rosy eye mutant of Aedes aegypti mosquito.	2001 Aug	12018585
Case of the month. Suspicion--an important EMS asset.	2001 Dec	11771370
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	11754528
Gas chromatographic-tandem mass spectrometric analytical method for the study of inhalation, potential dermal and actual exposure of agricultural workers to the pesticide malathion.	2001 Dec 21	11806548
[Biologic effect of diflubenzuron on Blattella germanica (Dictyoptera: Blattellidae)].	2001 Jan-Apr	11826538
An outbreak of Plasmodium falciparum malaria due to Anopheles minimus in central Assam, India.	2001 Mar-Jun	11963818
Non-Hodgkin's lymphoma and specific pesticide exposures in men: cross-Canada study of pesticides and health.	2001 Nov	11700263
Mechanism of inhibition of lysyl hydroxylase activity by the organophosphates malathion and malaoxon.	2001 Nov 1	11714250
Toxicological studies of organophosphate and pyrethroid insecticides for controlling the fruit fly Dacus ciliatus (Diptera: Tephritidae).	2001 Oct	11681666
Identification of butyrylcholinesterase adducts after inhibition with isomalathion using mass spectrometry: difference in mechanism between (1R)- and (1S)-stereoisomers.	2001 Oct 15	11601883
Protective effect of vitamin E in dimethoate and malathion induced oxidative stress in rat erythrocytes.	2001 Sep	11834209
Organic pollutants in surface waters from Portugal using chemometric interpretation.	2001 Sep	11816767
Designing safer (soft) drugs by avoiding the formation of toxic and oxidative metabolites.	2002	12013781
Esterase patterns and phylogenetic relationships of Drosophila species in the saltans subgroup (saltans group).	2002	11990758
Age-related alteration in hepatic disposition of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and pesticides.	2002 Apr	12076315
Field studies on the susceptibility of housefly to certain insecticides in nine Egyptian governorates.	2002 Apr	12049274
Solid-phase microextraction coupled to gas chromatography-mass spectrometry for the study of soil adsorption coefficients of organophosphorus pesticides.	2002 Aug	12195987
Monitoring of pesticide applicators for potential dermal exposure to malathion and biomarkers in urine.	2002 Aug 5	12191870
Biological monitoring of exposure to organophosphate pesticides.	2002 Aug 5	12191866
General anaesthesia for emergency surgery during acute organophosphate poisoning.	2002 Feb	11999602
Comparative in vitro pediculicidal efficacy of treatments in a resistant head lice population in the United States.	2002 Feb	11843643
Embryo-larval toxicity tests with the African catfish (Clarias gariepinus): comparative sensitivity of endpoints.	2002 Feb	11815818
Educational campaign versus malathion spraying for the control of Aedes aegypti in Colima, Mexico.	2002 Feb	11812816
Genotoxic effects of malathion: an organophosphorus insecticide, using three mammalian bioassays in vivo.	2002 Feb 15	11815260
Residues of methamidofos, malathion, and methiocarb in greenhouse crops.	2002 Feb 27	11853499
[Insecticide resistance of different populations of white-backed planthopper, Sogatella furcifera (Horváth) (Homoptera:Delphacidae)].	2002 Jan	11962304
Simple determination of 22 organophosphorous pesticides in human blood using headspace solid-phase microextraction and gas chromatography with mass spectrometric detection.	2002 Jan	11866384
Widespread insecticide resistance in head lice to the over-the-counter pediculocides in England, and the emergence of carbaryl resistance.	2002 Jan	11841371
Sister chromatid exchange and proliferative rate index in the longitudinal risk assessment of occupational exposure to pesticides.	2002 Jan	11827288
Transformation of Enterobacter gergoviae isolated from pink bollworm (Lepidoptera: Gelechiidae) gut with Bacillus thuringiensis toxin.	2002 Jan	11727033
Increased T-lymphocyte dependent antibody production in female SJL/J mice following exposure to commercial grade malathion.	2002 Jan 15	11750089
Cytogenetic studies on the effect of feeding mice with stored wheat grains treated with malathion.	2002 Jan 15	11719084
Size exclusion chromatographic cleanup for GC/MS determination of organophosphorus pesticide residues in household and vehicle dust.	2002 Jan-Feb	11878617
Determination of insecticides in honey by matrix solid-phase dispersion and gas chromatography with nitrogen-phosphorus detection and mass spectrometric confirmation.	2002 Jan-Feb	11878591
Assessment of organophosphorous pesticide exposures in the diets of preschool children in Washington State.	2002 Jan-Feb	11859430
Factors influencing nominal effective concentrations of chemical compounds in vitro: medium protein concentration.	2002 Jun	12020603
Observations on the domestic ecology of Rhodnius ecuadoriensis (Triatominae).	2002 Mar	12016443
Chemical predictors of wheeze among farmer pesticide applicators in the Agricultural Health Study.	2002 Mar 1	11874814
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	11936688
Removal of lindane and malathion from wastewater using bagasse fly ash--a sugar industry waste.	2002 May	12153014
Controversies concerning the treatment of lice and scabies.	2002 May	12004328
Clinical practice. Head lice.	2002 May 23	12023998
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	12113343
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	12106010

Patents

Sample Use Guides

In Vivo Use Guide

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

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.

Name

Type

Language

MALATHION

Common Name

English

MALATHION [MART.]

Common Name

English

ENT-17034

Code

English

MALATHION [VANDF]

Common Name

English

MALATHION [ORANGE BOOK]

Common Name

English

MALATHION [MI]

Common Name

English

MALATHION [IARC]

Common Name

English

Malathion [WHO-DD]

Common Name

English

MALATHION [EP MONOGRAPH]

Common Name

English

DIETHYL 2-((DIMETHOXYPHOSPHINOTHIOYL)THIO)BUTANEDIOATE

Systematic Name

English

DIETHYL (±)-MERCAPTOSUCCINATE, S-ESTER WITH O,O-DIMETHYL PHOSPHORODITHIOATE

Common Name

English

MALATHION [USP MONOGRAPH]

Common Name

English

8059HC

Code

English

BUTANEDIOIC ACID, ((DIMETHOXYPHOSPHINOTHIOYL)-THIO)-, DIETHYL ESTER, (±)-

Common Name

English

DIETHYL (DIMETHOXYPHOSPHINOTHIOYLTHIO)SUCCINATE

Systematic Name

English

MALATHION [HSDB]

Common Name

English

ENT 17,034

Code

English

NSC-6524

Code

English

BUTANEDIOIC ACID, ((DIMETHOXYPHOSPHINOTHIOYL)THIO)-, DIETHYL ESTER

Common Name

English

SUCCINIC ACID, MERCAPTO-, DIETHYL ESTER, S-ESTER WITH O,O-DIMETHYLPHOSPHORODITHIOATE

Common Name

English

MALATHION [USP-RS]

Common Name

English

OVIDE

Code

English

Classification Tree Code System Code

NDF-RT

N0000175723