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
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
| 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 |
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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Comparative residual toxicities of pesticides to the predator Agistemus industani (Acari: Stigmaeidae) on citrus in Florida. | 2001 |
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| Development of a SPME-GC-ECD methodology for selected pesticides in must and wine samples. | 2001 Apr |
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| In vivo changes in antioxidant systems and protective role of melatonin and a combination of vitamin C and vitamin E on oxidative damage in erythrocytes induced by chlorpyrifos-ethyl in rats. | 2001 Apr |
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| Distribution and abundance of insecticide resistant greenbugs (Homoptera: Aphididae) and validation of a bioassay to assess resistance. | 2001 Apr |
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| Decapitation impacting effect of topically applied chlorpyrifos on acetylcholinesterase and general esterases in susceptible and resistant German cockroaches (Dictyoptera: Blattellidae). | 2001 Apr |
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| Penetration of the eastern subterranean termite into soil treated at various thicknesses and concentrations of Dursban TC and Premise 75. | 2001 Apr |
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| Integrated control of oriental fruit moth (Lepidoptera: Tortricidae) in peach orchards using insecticide and mating disruption. | 2001 Apr |
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| Biomonitoring of persons exposed to insecticides used in residences. | 2001 Apr |
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| Analysis of the additivity of in vitro inhibition of cholinesterase by mixtures of chlorpyrifos-oxon and azinphos-methyl-oxon. | 2001 Apr 15 |
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| Influence of sebum and stratum corneum hydration on pesticide/herbicide collection efficiencies of the human hand. | 2001 Aug |
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| Identification of variants of CYP3A4 and characterization of their abilities to metabolize testosterone and chlorpyrifos. | 2001 Dec |
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| Diurnal variation in thermoregulatory response to chlorpyrifos and carbaryl in the rat. | 2001 Dec 14 |
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| Age-related effects of chlorpyrifos on acetylcholine release in rat brain. | 2001 Feb |
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| Effectiveness of a constructed wetland for retention of nonpoint-source pesticide pollution in the Lourens River catchment, South Africa. | 2001 Jan 15 |
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| Degradation of atrazine and several organophosphorus pesticides in oranges. | 2001 Jan-Feb |
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| Effects of chlorpyrifos in the plus-maze model of anxiety. | 2001 Jul |
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| An invertebrate model of the developmental neurotoxicity of insecticides: effects of chlorpyrifos and dieldrin in sea urchin embryos and larvae. | 2001 Jul |
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| Peripheral versus central muscarinic effects on blood pressure, cardiac contractility, heart rate, and body temperature in the rat monitored by radiotelemetry. | 2001 Jul |
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| Pesticide residues in oranges from Valencia (Spain). | 2001 Jul |
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| Lindane, chlorpyriphos, and quinalphos residues in mustard seed and oil. | 2001 Jul |
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| Cognitive function and cholinergic neurochemistry in weanling rats exposed to chlorpyrifos. | 2001 Jul 15 |
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| Embryo toxicity and teratogenicity of formaldehyde. | 2001 Jul-Aug |
|
| Dietary exposure to chlorpyrifos and levels of 3,5,6-trichloro-2-pyridinol in urine. | 2001 Jul-Aug |
|
| Stability of chlorpyrifos for termiticidal control in six Australian soils. | 2001 Jun |
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| Potential dermal and inhalation exposure to chlorpyrifos in Australian pesticide workers. | 2001 Jun |
|
| Rainfall-induced sediment and pesticide input from orchards into the Lourens River, Western Cape, South Africa: importance of a single event. | 2001 Jun |
|
| Persistent cholinergic presynaptic deficits after neonatal chlorpyrifos exposure. | 2001 Jun 1 |
|
| Acaricide toxicity and resistance in larvae of different strains of Tetranychus urticae and Panonychus ulmi (Acari: Tetranychidae). | 2001 Mar |
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| Monitoring of pesticide residues in Egyptian fruits and vegetables during 1996. | 2001 Mar-Apr |
|
| Metabolites of organophosphorous insecticides in urine specimens from inhabitants of a residential area. | 2001 May |
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| Acetylcholinesterase inhibition in the threeridge mussel (Amblema plicata) by chlorpyrifos: implications for biomonitoring. | 2001 May |
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| A modified extraction and clean-up procedure for the detection and determination of parathion-methyl and chlorpyrifos residues in tea. | 2001 May |
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| Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides. | 2001 May 15 |
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| Inhibition of calcium-stimulated ATPase in the hen brain P2 synaptosomal fraction by organophosphorus esters: relevance to delayed neuropathy. | 2001 May 25 |
|
| Simultaneous determination of chlorpyrifos, permethrin, and their metabolites in rat plasma and urine by high-performance liquid chromatography. | 2001 May-Jun |
|
| Transferable residues from dog fur and plasma cholinesterase inhibition in dogs treated with a flea control dip containing chlorpyrifos. | 2001 Nov |
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| A comparison of biomarker responses in the earthworm Aporrectodea caliginosa to the organophosphorus insecticides diazinon and chlorpyrifos. | 2001 Nov |
|
| Effect of pulse frequency and interval on the toxicity of chlorpyrifos to Daphnia magna. | 2001 Nov |
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| Chlorpyrifos-induced hsp70 expression and effect on reproductive performance in transgenic Drosophila melanogaster (hsp70-lacZ) Bg9. | 2001 Nov |
|
| Modification, by the insecticide chlorpyrifos, of the behavioral response to kairomones of a parasitoid wasp, Leptopilina boulardi. | 2001 Nov |
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| Transfer of ingested insecticides among cockroaches: effects of active ingredient, bait formulation, and assay procedures. | 2001 Oct |
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| Insecticide susceptibility in Coptotermes formosanus and Reticulitermes virginicus (Isoptera: Rhinotermitidae). | 2001 Oct |
|
| Management of early-instar Japanese beetle (Coleoptera: Searabaeidae) in field-grown nursery crops. | 2001 Oct |
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| Neonatal chlorpyrifos administration elicits deficits in immune function in adulthood: a neural effect? | 2001 Oct 24 |
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| Developmental neurotoxicity of chlorpyrifos modeled in vitro: comparative effects of metabolites and other cholinesterase inhibitors on DNA synthesis in PC12 and C6 cells. | 2001 Sep |
|
| Detection of insecticide resistance in Aedes aegypti (Diptera: Culicidae) from Cuba and Venezuela. | 2001 Sep |
|
| Pesticide poisoning in a free-ranging lappet-faced vulture (Torgos tracheliotus). | 2001 Sep 29 |
|
| Multiresidue determination of pesticides in drinking and related waters by gas chromatography/mass spectrometry after solid-phase extraction: interlaboratory study. | 2001 Sep-Oct |
|
| Zinc supplementation prevents liver injury in chlorpyrifos-treated rats. | 2001 Summer |
|
| Esterase inhibition in SH-SY5Y human neuroblastoma cells following exposure to organophosphorus compounds for 28 days. | 2001 Summer |
Sample Use Guides
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
| Substance Class |
Chemical
Created
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JCS58I644W
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59101
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chlorpyrifos
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CHLORPYRIFOS
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| Related Record | Type | Details | ||
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METABOLIC ENZYME -> INHIBITOR |
Chlorpyrifos inhibited CYP1A1/2 activities more than 90%.
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> INHIBITOR |
Screening of potential CYP2B6 inhibitions illustrates that CYP2B6 activity was extensively inhibited by all tested organophosphate pesticides. Inhibition percentages were 100% with chlorpyrifos.
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> INHIBITOR |
Chlorpyrifos inhibited CYP1A1/2 activities more than 90%.
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METABOLIC ENZYME -> SUBSTRATE |
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IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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IN VITRO
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