CHLORPYRIFOS

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H11Cl3NO3PS
Molecular Weight	350.586
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOP(=S)(OCC)OC1=C(Cl)C=C(Cl)C(Cl)=N1

InChI

InChIKey=SBPBAQFWLVIOKP-UHFFFAOYSA-N

InChI=1S/C9H11Cl3NO3PS/c1-3-14-17(18,15-4-2)16-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C9H11Cl3NO3PS
Molecular Weight	350.586
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.hmdb.ca/metabolites/HMDB0041856 | http://npic.orst.edu/factsheets/archive/chlorptech.html#references | https://www.ncbi.nlm.nih.gov/pubmed/26002045

Chlorpyrifos (CPF) is a crystalline organophosphate insecticide. It was introduced in 1965 by Dow Chemical Company and is known by many trade names (see table), including Dursban and Lorsban. It acts on the nervous system of insects by inhibiting acetylcholinesterase. Chlorpyrifos is an organophosphate, with potential for both acute toxicity at larger amounts and neurological effects in fetuses and children even at very small amounts. For acute effects, the EPA classifies chlorpyrifos as Class II: moderately toxic. CPF is a strongly genotoxic agent that induces DNA damage and cell apoptosis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Acetylcholinesterase 209 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26165232 \| https://www.ncbi.nlm.nih.gov/pubmed/21983245 \| https://www.ncbi.nlm.nih.gov/pubmed/17644233	Inhibitor 8504	0.12 µM [IC50]
Neutral cholesterol ester hydrolase 1 1 Target ID: CHEMBL5428 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16449251	Inhibitor 8504	8.0 nM [IC50]
Monoglyceride lipase 8 Target ID: CHEMBL5774 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16449251	Inhibitor 8504	34.0 nM [IC50]
Cholesterol esterase 1 Target ID: CHEMBL2988 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16449251	Inhibitor 8504	5.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Diurnal variation in thermoregulatory response to chlorpyrifos and carbaryl in the rat.	2001-12-14	11718951
Identification of variants of CYP3A4 and characterization of their abilities to metabolize testosterone and chlorpyrifos.	2001-12	11714865
Transferable residues from dog fur and plasma cholinesterase inhibition in dogs treated with a flea control dip containing chlorpyrifos.	2001-11	11712994
A comparison of biomarker responses in the earthworm Aporrectodea caliginosa to the organophosphorus insecticides diazinon and chlorpyrifos.	2001-11	11699775
Effect of pulse frequency and interval on the toxicity of chlorpyrifos to Daphnia magna.	2001-11	11680745
Chlorpyrifos-induced hsp70 expression and effect on reproductive performance in transgenic Drosophila melanogaster (hsp70-lacZ) Bg9.	2001-11	11598781
Modification, by the insecticide chlorpyrifos, of the behavioral response to kairomones of a parasitoid wasp, Leptopilina boulardi.	2001-11	11598780
Neonatal chlorpyrifos administration elicits deficits in immune function in adulthood: a neural effect?	2001-10-24	11675126
Multiresidue determination of pesticides in drinking and related waters by gas chromatography/mass spectrometry after solid-phase extraction: interlaboratory study.	2001-10-17	11601461
Transfer of ingested insecticides among cockroaches: effects of active ingredient, bait formulation, and assay procedures.	2001-10	11681688
Insecticide susceptibility in Coptotermes formosanus and Reticulitermes virginicus (Isoptera: Rhinotermitidae).	2001-10	11681687
Management of early-instar Japanese beetle (Coleoptera: Searabaeidae) in field-grown nursery crops.	2001-10	11681678
Monitoring of organochlorine and organophosphorus pesticides in the water of the Reconquista River (Buenos Aires, Argentina).	2001-10	11547868
Pesticide poisoning in a free-ranging lappet-faced vulture (Torgos tracheliotus).	2001-09-29	11601520
Embryo toxicity and teratogenicity of formaldehyde.	2001-09-27	11572272
Persistent behavioral consequences of neonatal chlorpyrifos exposure in rats.	2001-09-23	11557096
Alterations in serotonin transporter expression in brain regions of rats exposed neonatally to chlorpyrifos.	2001-09-23	11557094
The toxicity of chlorpyrifos towards differentiating mouse N2a neuroblastoma cells.	2001-09-22	11566565
Developmental neurotoxicity of chlorpyrifos modeled in vitro: comparative effects of metabolites and other cholinesterase inhibitors on DNA synthesis in PC12 and C6 cells.	2001-09	11673119
Detection of insecticide resistance in Aedes aegypti (Diptera: Culicidae) from Cuba and Venezuela.	2001-09	11580033
Chlorothalonil and chlorpyrifos degradation products in golf course leachate.	2001-09	11561404
Effect of short-term exposure to chlorpyrifos on developmental parameters and biochemical biomarkers in Chironomus riparius Meigen.	2001-09	11534949
Effects of atrazine on acetylcholinesterase activity in midges (Chironomus tentans) exposed to organophosphorus insecticides.	2001-09	11534899
Hydrolysis of chlorpyrifos in natural waters of the Chesapeake Bay.	2001-09	11513107
Metabolism of chlorpyrifos by human cytochrome P450 isoforms and human, mouse, and rat liver microsomes.	2001-09	11502728
Analysis of 3,5,6-trichloro-2-pyridinol in urine samples from the general population using gas chromatography-mass spectrometry after steam distillation and solid-phase extraction.	2001-08-05	11499628
Evaluation of acute sensory--motor effects and test sensitivity using termiticide workers exposed to chlorpyrifos.	2001-08-04	11485841
Artificial carbon dioxide source to attract lesser cornstalk borer (Lepidoptera: Pyralidae) larvae.	2001-08	11561844
Environmental distribution of acetochlor, atrazine, chlorpyrifos, and propisochlor under field conditions.	2001-08	11513679
Influence of sebum and stratum corneum hydration on pesticide/herbicide collection efficiencies of the human hand.	2001-08	11504356
Environmental residues and biomonitoring estimates of human insecticide exposure from treated residential turf.	2001-08	11462149
Effects of dissolved organic matter from animal waste effluent on chlorpyrifos sorption by soils.	2001-07-31	11476503
Cognitive function and cholinergic neurochemistry in weanling rats exposed to chlorpyrifos.	2001-07-15	11446824
Effects of chlorpyrifos in the plus-maze model of anxiety.	2001-07	11548114
An invertebrate model of the developmental neurotoxicity of insecticides: effects of chlorpyrifos and dieldrin in sea urchin embryos and larvae.	2001-07	11485862
Peripheral versus central muscarinic effects on blood pressure, cardiac contractility, heart rate, and body temperature in the rat monitored by radiotelemetry.	2001-07	11484908
Pesticide residues in oranges from Valencia (Spain).	2001-07	11469317
Quantification of nicotine, chlorpyrifos and their metabolites in rat plasma and urine using high-performance liquid chromatography.	2001-06-15	11417874
Measurement of children's exposure to pesticides: analysis of urinary metabolite levels in a probability-based sample.	2001-06	11445512
Biochemical mechanisms of resistance in strains of Oryzaephilus surinamensis (Coleoptera: Silvanidae) resistant to malathion and chlorpyrifos-methyl.	2001-06	11425027
Attractiveness of insecticide baits for cockroach control (Dictyoptera: Blattellidae): laboratory and field studies.	2001-06	11425024
Pesticide storage and release in unsaturated soil in Illinois, USA.	2001-05	11411849
Dietary exposure to chlorpyrifos and levels of 3,5,6-trichloro-2-pyridinol in urine.	2001-03-13	11571607
Acaricide toxicity and resistance in larvae of different strains of Tetranychus urticae and Panonychus ulmi (Acari: Tetranychidae).	2001-03	11455655
Chlorpyrifos induced alterations in levels of thiobarbituric acid reactive substances and glutathione in rat brain.	2001-02	11480216
Determination of pesticide residues in fruits and vegetables in Islamabad market.	2001-01	11480355
Comparative residual toxicities of pesticides to the predator Agistemus industani (Acari: Stigmaeidae) on citrus in Florida.	2001	11697784
Zinc supplementation prevents liver injury in chlorpyrifos-treated rats.	2001	11697766
Esterase inhibition in SH-SY5Y human neuroblastoma cells following exposure to organophosphorus compounds for 28 days.	2001	11690566
Modeled estimates of chlorpyrifos exposure and dose for the Minnesota and Arizona NHEXAS populations.	2000-08-14	11477522

Patents

Sample Use Guides

In Vivo Use Guide

Male volunteers consumed doses up to 0.1 mg/kg/day for up to seven weeks. Significant plasma cholinesterase inhibition was observed, which ranged from 36-82% at the highest dose after nine days of treatment.

Route of Administration: Oral

In Vitro Use Guide

Acute exposure of PC12 cells to chlorpyrifos and its metabolite chlorpyrifos-oxon (10uM) induced a modest increase in basal [Ca(2+)]i. Chlorpyrifos already induced a ∼30% inhibition at 0.1uM and a 100% inhibition at 10uM (IC50=0.43uM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:54:53 GMT 2025` Edited by `admin` on `Mon Mar 31 17:54:53 GMT 2025`
Record UNII	JCS58I644W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENT-27311

Preferred Name

English

CHLORPYRIFOS

Common Name

English

CHLORPYRIFOS [MI]

Common Name

English

CHLORPYRIFOS [MART.]

Common Name

English

CHLORPYRIFOS [HSDB]

Common Name

English

CHLOROPYRIFOS

Common Name

English

NSC-755891

Code

English

O,O-DIETHYL O-(3,5,6-TRICHLORO-2-PYRIDINYL) PHOSPHOROTHIOATE

Systematic Name

English

CHLORPYRIFOS [ISO]

Common Name

English

O,O-DIETHYL O-3,5,6-TRICHLORO-2-PYRIDYL PHOSPHOROTHIOATE

Common Name

English

DURSBAN

Brand Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

59101