Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H11Cl3NO3PS |
| Molecular Weight | 350.5875 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOP(=S)(OCC)Oc1c(cc(c(Cl)n1)Cl)Cl
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 | 350.5875 |
| 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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| Artificial carbon dioxide source to attract lesser cornstalk borer (Lepidoptera: Pyralidae) larvae. | 2001 Aug |
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| Environmental distribution of acetochlor, atrazine, chlorpyrifos, and propisochlor under field conditions. | 2001 Aug |
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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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| Environmental residues and biomonitoring estimates of human insecticide exposure from treated residential turf. | 2001 Aug |
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| 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 Aug 5 |
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| The toxicity of chlorpyrifos towards differentiating mouse N2a neuroblastoma cells. | 2001 Aug-Oct |
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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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| Chlorpyrifos induced alterations in levels of thiobarbituric acid reactive substances and glutathione in rat brain. | 2001 Feb |
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| Determination of pesticide residues in fruits and vegetables in Islamabad market. | 2001 Jan |
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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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| Pesticide residues in oranges from Valencia (Spain). | 2001 Jul |
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| Cognitive function and cholinergic neurochemistry in weanling rats exposed to chlorpyrifos. | 2001 Jul 15 |
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| Dietary exposure to chlorpyrifos and levels of 3,5,6-trichloro-2-pyridinol in urine. | 2001 Jul-Aug |
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| Effects of dissolved organic matter from animal waste effluent on chlorpyrifos sorption by soils. | 2001 Jul-Aug |
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| Measurement of children's exposure to pesticides: analysis of urinary metabolite levels in a probability-based sample. | 2001 Jun |
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| Biochemical mechanisms of resistance in strains of Oryzaephilus surinamensis (Coleoptera: Silvanidae) resistant to malathion and chlorpyrifos-methyl. | 2001 Jun |
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| Attractiveness of insecticide baits for cockroach control (Dictyoptera: Blattellidae): laboratory and field studies. | 2001 Jun |
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| Stability of chlorpyrifos for termiticidal control in six Australian soils. | 2001 Jun |
|
| Quantification of nicotine, chlorpyrifos and their metabolites in rat plasma and urine using high-performance liquid chromatography. | 2001 Jun 15 |
|
| Inhibition of cholinesterase enzymes following a single dermal dose of chlorpyrifos and methyl parathion, alone and in combination, in pregnant rats. | 2001 Jun 8 |
|
| Acaricide toxicity and resistance in larvae of different strains of Tetranychus urticae and Panonychus ulmi (Acari: Tetranychidae). | 2001 Mar |
|
| Environmental toxicant effects on neuroendocrine function. | 2001 Mar |
|
| Pesticide storage and release in unsaturated soil in Illinois, USA. | 2001 May |
|
| Metabolites of organophosphorous insecticides in urine specimens from inhabitants of a residential area. | 2001 May |
|
| Acetylcholinesterase inhibition in the threeridge mussel (Amblema plicata) by chlorpyrifos: implications for biomonitoring. | 2001 May |
|
| 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 |
|
| 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 |
|
| Transfer of ingested insecticides among cockroaches: effects of active ingredient, bait formulation, and assay procedures. | 2001 Oct |
|
| 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 |
|
| Monitoring of organochlorine and organophosphorus pesticides in the water of the Reconquista River (Buenos Aires, Argentina). | 2001 Oct |
|
| Neonatal chlorpyrifos administration elicits deficits in immune function in adulthood: a neural effect? | 2001 Oct 24 |
|
| Detection of insecticide resistance in Aedes aegypti (Diptera: Culicidae) from Cuba and Venezuela. | 2001 Sep |
|
| Chlorothalonil and chlorpyrifos degradation products in golf course leachate. | 2001 Sep |
|
| Effect of short-term exposure to chlorpyrifos on developmental parameters and biochemical biomarkers in Chironomus riparius Meigen. | 2001 Sep |
|
| Effects of atrazine on acetylcholinesterase activity in midges (Chironomus tentans) exposed to organophosphorus insecticides. | 2001 Sep |
|
| Hydrolysis of chlorpyrifos in natural waters of the Chesapeake Bay. | 2001 Sep |
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| Metabolism of chlorpyrifos by human cytochrome P450 isoforms and human, mouse, and rat liver microsomes. | 2001 Sep |
|
| Persistent behavioral consequences of neonatal chlorpyrifos exposure in rats. | 2001 Sep 23 |
|
| Alterations in serotonin transporter expression in brain regions of rats exposed neonatally to chlorpyrifos. | 2001 Sep 23 |
|
| Pesticide poisoning in a free-ranging lappet-faced vulture (Torgos tracheliotus). | 2001 Sep 29 |
|
| Zinc supplementation prevents liver injury in chlorpyrifos-treated rats. | 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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| Record UNII |
JCS58I644W
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59101
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SUB33137
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CHLORPYRIFOS
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CHEMBL463210
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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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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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ACTIVE MOIETY |
