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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.12 µM [IC50]
8.0 nM [IC50]
34.0 nM [IC50]
5.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
JCS58I644W
Record Status Validated (UNII)
Record Version