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 |
|
| 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 |
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
by
admin
on
Edited
Fri Jun 25 21:50:45 UTC 2021
by
admin
on
Fri Jun 25 21:50:45 UTC 2021
|
| Record UNII |
JCS58I644W
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
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 | ||
|---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
METABOLITE -> PARENT |
IN VITRO
|
||
|
METABOLITE -> PARENT |
IN VITRO
|
||
|
|
PARENT -> METABOLITE | |||
|
METABOLITE -> PARENT |
IN VITRO
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
