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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
Structure of CHLORPYRIFOS

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

HIDE SMILES / InChI

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.

CNS Activity

Curator's Comment:: Central nervous system signs include diminished appetite, anxiety, restlessness, hyperactivity, depression, clonic-tonic seizures, depressed respiration, and coma.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Comparative residual toxicities of pesticides to the predator Agistemus industani (Acari: Stigmaeidae) on citrus in Florida.
2001
Use of human data for the derivation of a reference dose for chlorpyrifos.
2001 Apr
An insensitive acetylcholinesterase confers resistance to methomyl in the beet armyworm Spodoptera exigua (Lepidoptera: Noctuidae).
2001 Apr
Analysis of the additivity of in vitro inhibition of cholinesterase by mixtures of chlorpyrifos-oxon and azinphos-methyl-oxon.
2001 Apr 15
Artificial carbon dioxide source to attract lesser cornstalk borer (Lepidoptera: Pyralidae) larvae.
2001 Aug
Environmental distribution of acetochlor, atrazine, chlorpyrifos, and propisochlor under field conditions.
2001 Aug
Influence of sebum and stratum corneum hydration on pesticide/herbicide collection efficiencies of the human hand.
2001 Aug
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
The toxicity of chlorpyrifos towards differentiating mouse N2a neuroblastoma cells.
2001 Aug-Oct
Identification of variants of CYP3A4 and characterization of their abilities to metabolize testosterone and chlorpyrifos.
2001 Dec
Diurnal variation in thermoregulatory response to chlorpyrifos and carbaryl in the rat.
2001 Dec 14
Effects of chlorpyrifos in the plus-maze model of anxiety.
2001 Jul
An invertebrate model of the developmental neurotoxicity of insecticides: effects of chlorpyrifos and dieldrin in sea urchin embryos and larvae.
2001 Jul
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
Evaluation of acute sensory--motor effects and test sensitivity using termiticide workers exposed to chlorpyrifos.
2001 Jul-Aug
Determinants of chlorpyrifos exposures and urinary 3,5,6-trichloro-2-pyridinol levels among termiticide applicators.
2001 Jun
Potential dermal and inhalation exposure to chlorpyrifos in Australian pesticide workers.
2001 Jun
Use of a pharmacokinetic model to assess chlorpyrifos exposure and dose in children, based on urinary biomarker measurements.
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
Inhibition of cholinesterase enzymes following a single dermal dose of chlorpyrifos and methyl parathion, alone and in combination, in pregnant rats.
2001 Jun 8
Environmental toxicant effects on neuroendocrine function.
2001 Mar
Function testing for chemical brain damage: a review.
2001 Mar-Apr
Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides.
2001 May 15
Inhibition of calcium-stimulated ATPase in the hen brain P2 synaptosomal fraction by organophosphorus esters: relevance to delayed neuropathy.
2001 May 25
Modeled estimates of chlorpyrifos exposure and dose for the Minnesota and Arizona NHEXAS populations.
2001 May-Jun
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
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
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
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
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
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
Patents

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
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 Fri Jun 25 21:50:45 UTC 2021
Edited
by admin
on Fri Jun 25 21:50:45 UTC 2021
Record UNII
JCS58I644W
Record Status Validated (UNII)
Record Version
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Name Type Language
CHLORPYRIFOS
HSDB   ISO   MART.   MI  
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
ENT-27311
Code English
DURSBAN
Brand Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 59101
Created by admin on Fri Jun 25 21:50:45 UTC 2021 , Edited by admin on Fri Jun 25 21:50:45 UTC 2021
Code System Code Type Description
MESH
D004390
Created by admin on Fri Jun 25 21:50:45 UTC 2021 , Edited by admin on Fri Jun 25 21:50:45 UTC 2021
PRIMARY
HSDB
389
Created by admin on Fri Jun 25 21:50:45 UTC 2021 , Edited by admin on Fri Jun 25 21:50:45 UTC 2021
PRIMARY
CAS
2921-88-2
Created by admin on Fri Jun 25 21:50:45 UTC 2021 , Edited by admin on Fri Jun 25 21:50:45 UTC 2021
PRIMARY
MERCK INDEX
M3465
Created by admin on Fri Jun 25 21:50:45 UTC 2021 , Edited by admin on Fri Jun 25 21:50:45 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
220-864-4
Created by admin on Fri Jun 25 21:50:45 UTC 2021 , Edited by admin on Fri Jun 25 21:50:45 UTC 2021
PRIMARY
FDA UNII
JCS58I644W
Created by admin on Fri Jun 25 21:50:45 UTC 2021 , Edited by admin on Fri Jun 25 21:50:45 UTC 2021
PRIMARY
PUBCHEM
2730
Created by admin on Fri Jun 25 21:50:45 UTC 2021 , Edited by admin on Fri Jun 25 21:50:45 UTC 2021
PRIMARY
EVMPD
SUB33137
Created by admin on Fri Jun 25 21:50:45 UTC 2021 , Edited by admin on Fri Jun 25 21:50:45 UTC 2021
PRIMARY
WIKIPEDIA
CHLORPYRIFOS
Created by admin on Fri Jun 25 21:50:45 UTC 2021 , Edited by admin on Fri Jun 25 21:50:45 UTC 2021
PRIMARY
EPA CompTox
2921-88-2
Created by admin on Fri Jun 25 21:50:45 UTC 2021 , Edited by admin on Fri Jun 25 21:50:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL463210
Created by admin on Fri Jun 25 21:50:45 UTC 2021 , Edited by admin on Fri Jun 25 21:50:45 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INHIBITOR
Chlorpyrifos inhibited CYP1A1/2 activities more than 90%.
METABOLIC ENZYME -> SUBSTRATE
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.
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
Chlorpyrifos inhibited CYP1A1/2 activities more than 90%.
METABOLIC ENZYME -> SUBSTRATE
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