U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of CHLORPYRIFOS

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

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
Decapitation impacting effect of topically applied chlorpyrifos on acetylcholinesterase and general esterases in susceptible and resistant German cockroaches (Dictyoptera: Blattellidae).
2001 Apr
Purification and characterization of trans-permethrin metabolizing microsomal esterases from workers of the eastern subterranean termite, Reticulitermes flavipes (Kollar).
2001 Apr 27
Influence of sebum and stratum corneum hydration on pesticide/herbicide collection efficiencies of the human hand.
2001 Aug
Diurnal variation in thermoregulatory response to chlorpyrifos and carbaryl in the rat.
2001 Dec 14
Effects of repeated oral postnatal exposure to chlorpyrifos on open-field behavior in juvenile rats.
2001 Feb
Toxicokinetic interactions and survival of Hyalella azteca exposed to binary mixtures of chlorpyrifos, dieldrin, and methyl mercury.
2001 Feb
Effectiveness of a constructed wetland for retention of nonpoint-source pesticide pollution in the Lourens River catchment, South Africa.
2001 Jan 15
Degradation of atrazine and several organophosphorus pesticides in oranges.
2001 Jan-Feb
Comparing cognitive and screening tests for neurotoxicity. Effects of acute chlorpyrifos on visual signal detection and a neurobehavioral test battery in rats.
2001 Jan-Feb
On predicting multi-route and multimedia residential exposure to chlorpyrifos and diazinon.
2001 Jan-Feb
Pesticide residues in oranges from Valencia (Spain).
2001 Jul
Stability of chlorpyrifos for termiticidal control in six Australian soils.
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
Changes in EEG power spectra and behavioral states in rats exposed to the acetylcholinesterase inhibitor chlorpyrifos and muscarinic agonist oxotremorine.
2001 Mar 2
Function testing for chemical brain damage: a review.
2001 Mar-Apr
Gene therapy to prevent organophosphate intoxication.
2001 May 15
Modeled estimates of chlorpyrifos exposure and dose for the Minnesota and Arizona NHEXAS populations.
2001 May-Jun
Transferable residues from dog fur and plasma cholinesterase inhibition in dogs treated with a flea control dip containing chlorpyrifos.
2001 Nov
Effect of pulse frequency and interval on the toxicity of chlorpyrifos to Daphnia magna.
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
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
Multiresidue determination of pesticides in drinking and related waters by gas chromatography/mass spectrometry after solid-phase extraction: interlaboratory study.
2001 Sep-Oct
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 Dec 15 15:21:05 GMT 2023
Edited
by admin
on Fri Dec 15 15:21:05 GMT 2023
Record UNII
JCS58I644W
Record Status Validated (UNII)
Record Version
  • Download
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 Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
Code System Code Type Description
MESH
D004390
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
ALANWOOD
chlorpyrifos
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
HSDB
389
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
CAS
2921-88-2
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
MERCK INDEX
m3465
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
220-864-4
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
FDA UNII
JCS58I644W
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
NSC
755891
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
PUBCHEM
2730
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
EVMPD
SUB33137
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
CHEBI
34631
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
WIKIPEDIA
CHLORPYRIFOS
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
SMS_ID
100000125916
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
NCI_THESAURUS
C163641
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID4020458
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
PRIMARY
ChEMBL
CHEMBL463210
Created by admin on Fri Dec 15 15:21:05 GMT 2023 , Edited by admin on Fri Dec 15 15:21:05 GMT 2023
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
Related Record Type Details
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
PARENT -> METABOLITE
METABOLITE -> PARENT
IN VITRO
Related Record Type Details
ACTIVE MOIETY