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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| Use of human data for the derivation of a reference dose for chlorpyrifos. | 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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| Integrated control of oriental fruit moth (Lepidoptera: Tortricidae) in peach orchards using insecticide and mating disruption. | 2001 Apr |
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| Effects of field applied residues and length of exposure to tebufenozide on the obliquebanded leafroller (Lepidoptera: Tortricidae). | 2001 Apr |
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| Biomonitoring of persons exposed to insecticides used in residences. | 2001 Apr |
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| Artificial carbon dioxide source to attract lesser cornstalk borer (Lepidoptera: Pyralidae) larvae. | 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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| 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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| Intermediate syndrome secondary to ingestion of chlorpiriphos. | 2001 Feb |
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| Effects of repeated oral postnatal exposure to chlorpyrifos on open-field behavior in juvenile rats. | 2001 Feb |
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| Does the developmental neurotoxicity of chlorpyrifos involve glial targets? Macromolecule synthesis, adenylyl cyclase signaling, nuclear transcription factors, and formation of reactive oxygen in C6 glioma cells. | 2001 Feb 9 |
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| Developmental stage-specific life-cycle bioassay for assessment of sediment-associated toxicant effects on benthic copepod production. | 2001 Jan |
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| On predicting multi-route and multimedia residential exposure to chlorpyrifos and diazinon. | 2001 Jan-Feb |
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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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| Embryo toxicity and teratogenicity of formaldehyde. | 2001 Jul-Aug |
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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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| Biochemical mechanisms of resistance in strains of Oryzaephilus surinamensis (Coleoptera: Silvanidae) resistant to malathion and chlorpyrifos-methyl. | 2001 Jun |
|
| Quantification of nicotine, chlorpyrifos and their metabolites in rat plasma and urine using high-performance liquid chromatography. | 2001 Jun 15 |
|
| Acaricide toxicity and resistance in larvae of different strains of Tetranychus urticae and Panonychus ulmi (Acari: Tetranychidae). | 2001 Mar |
|
| Toxicity of chlorypyrifos to Rana pipiens embryos. | 2001 Mar |
|
| Changes in EEG power spectra and behavioral states in rats exposed to the acetylcholinesterase inhibitor chlorpyrifos and muscarinic agonist oxotremorine. | 2001 Mar 2 |
|
| Reanalysis with optimized power of red blood cell acetylcholinesterase activity from a 1-year dietary treatment of dogs to chlorpyrifos. | 2001 Mar 7 |
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| Function testing for chemical brain damage: a review. | 2001 Mar-Apr |
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| Pesticide storage and release in unsaturated soil in Illinois, USA. | 2001 May |
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| Further considerations of the skeletal system as a biomarker of episodic chlorpyrifos exposure. | 2001 May |
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| Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides. | 2001 May 15 |
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| Gene therapy to prevent organophosphate intoxication. | 2001 May 15 |
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| Modeled estimates of chlorpyrifos exposure and dose for the Minnesota and Arizona NHEXAS populations. | 2001 May-Jun |
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| Simultaneous determination of chlorpyrifos, permethrin, and their metabolites in rat plasma and urine by high-performance liquid chromatography. | 2001 May-Jun |
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| Transferable residues from dog fur and plasma cholinesterase inhibition in dogs treated with a flea control dip containing chlorpyrifos. | 2001 Nov |
|
| 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 |
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| 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 |
|
| Neonatal chlorpyrifos administration elicits deficits in immune function in adulthood: a neural effect? | 2001 Oct 24 |
|
| 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 |
|
| Effects of atrazine on acetylcholinesterase activity in midges (Chironomus tentans) exposed to organophosphorus insecticides. | 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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| Record UNII |
JCS58I644W
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| Record Status |
Validated (UNII)
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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 |
