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

Stereochemistry ACHIRAL
Molecular Formula C10H14NO6P
Molecular Weight 275.195
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PARAOXON

SMILES

CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O

InChI

InChIKey=WYMSBXTXOHUIGT-UHFFFAOYSA-N
InChI=1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

HIDE SMILES / InChI
Paraoxon is an odorless, reddish-yellow oil. Paraoxon is an aryl dialkyl phosphate where both the alkyl groups are ethyl and the aryl group is 4-nitrophenyl. It is a cholinesterase or acetylcholinesterase (AChE) inhibitor. It is an organophosphate oxon, and the active metabolite of the insecticide parathion. Paraoxon is one of the most potent acetylcholinesterase-inhibiting insecticides available, around 70% as potent as the nerve agent sarin, and so is now rarely used as an insecticide due to the risk of poisoning to humans and other animals. Exposure to Paraoxon can cause rapid, severe organophosphate poisoning with headache, sweating, nausea and vomiting, diarrhea, loss of coordination, and death. Paraoxon is on the Hazardous Substance List because it is cited by DOT and EPA. Parathion is converted in the body in part to paraoxon, a strong inhibitor of the enzyme acetyl cholinesterase. Upon inhibition of this enzyme in the tissues, acetylcholine, the substance responsible for transmission of nerve impulses in much of the nervous system, accumulates, producing an initial overstimulation and subsequent blockage of nerve stimuli. Paraoxon was once used as an opthamological drug against glaucoma.

Approval Year

PubMed

PubMed

TitleDatePubMed
1H-MRS detected lipolysis in diabetic rat hearts requires neutral lipase.
2001
Insecticides and atherosclerosis.
2001 Aug
Organophosphorus compounds alter intracellular F-actin content in SH-SY5Y human neuroblastoma cells.
2001 Dec
Development of a quantitative relationship between inhibition percentage and both incubation time and inhibitor concentration for inhibition biosensors--theoretical and practical considerations.
2001 Dec
Mobility of the active site bound paraoxon and sarin in zinc-phosphotriesterase by molecular dynamics simulation and quantum chemical calculation.
2001 Feb 7
Resolving pathways of interaction of covalent inhibitors with the active site of acetylcholinesterases: MALDI-TOF/MS analysis of various nerve agent phosphyl adducts.
2001 Jul
Purification and characterization of carbaryl hydrolase from Arthrobacter sp. RC100.
2001 Jul 10
Influence of the conformational flexibility on the kinetics and dimerisation process of two Candida rugosa lipase isoenzymes.
2001 Jul 13
High-dose intravenous paraoxon exposure does not cause organophosphate-induced delayed neuropathy (OPIDN) in mini pigs.
2001 Jul-Aug
Glucose feeding exacerbates parathion-induced neurotoxicity.
2001 Jun 22
Flow-injection spectrophotometric determination of paraoxon by its inhibitory effect on the enzyme acetylcholinesterase.
2001 May
Interactions of rat brain acetylcholinesterase with the detergent Triton X-100 and the organophosphate paraoxon.
2001 Oct
Amperometric microbial biosensor for direct determination of organophosphate pesticides using recombinant microorganism with surface expressed organophosphorus hydrolase.
2001 Sep
Dipeptide model prodrugs for the intestinal oligopeptide transporter. Affinity for and transport via hPepT1 in the human intestinal Caco-2 cell line.
2001 Sep 11
Lipolytic activity of ricin from Ricinus sanguineus and Ricinus communis on neutral lipids.
2001 Sep 15
Esterase inhibition in SH-SY5Y human neuroblastoma cells following exposure to organophosphorus compounds for 28 days.
2001 Summer
Species- and substrate-specific stimulation of human plasma paraoxonase 1 (PON1) activity by high chloride concentration.
2002
Flow-injection amperometric determination of pesticides on the basis of their inhibition of immobilized acetylcholinesterases of different origin.
2002 Apr
Serum paraoxonase activity changes in patients with Alzheimer's disease and vascular dementia.
2002 Apr
Addition of Polybrene improves stability of organophosphate hydrolase immobilized in poly(vinyl alcohol) cryogel carrier.
2002 Apr 18
Synthesis of a novel cyclic prodrug of RGD peptidomimetic to improve its cell membrane permeation.
2002 Aug
Vitamin C and E intake is associated with increased paraoxonase activity.
2002 Aug 1
Rapid assessment of organophosphorous/carbamate exposure in the bivalve mollusc Mytilus edulis using combined esterase activities as biomarkers.
2002 Dec 3
Atorvastatin preferentially reduces LDL-associated platelet-activating factor acetylhydrolase activity in dyslipidemias of type IIA and type IIB.
2002 Feb 1
Catalytic buffers enable positive-response inhibition-based sensing of nerve agents.
2002 Feb 5
In vitro effects of organophosphorus anticholinesterases on muscarinic receptor-mediated inhibition of acetylcholine release in rat striatum.
2002 Jan 15
In vitro effects of chlorpyrifos, parathion, methyl parathion and their oxons on cardiac muscarinic receptor binding in neonatal and adult rats.
2002 Jan 15
GFP-visualized immobilized enzymes: degradation of paraoxon via organophosphorus hydrolase in a packed column.
2002 Jan 20
Intravenous L-lactate application in minipigs partially protects acetylcholinesteratic but not butyrylcholinesteratic activity in plasma from inhibition by paraoxon.
2002 Jul
Continuous system modeling of equilibrium dialysis for determinations of tissue partitioning of parathion and paraoxon.
2002 Jul 21
Effects of PCB exposure on the toxic impact of organophosphorus insecticides.
2002 Jun
Nanocrystalline metal oxides as destructive adsorbents for organophosphorus compounds at ambient temperatures.
2002 Jun 3
Tricyclic cyanoguanidines: synthesis, site of action and insecticidal activity of a novel class of reversible acetylcholinesterase inhibitors.
2002 Mar
Cerivastatin modulates plasma paraoxonase/arylesterase activity and oxidant-antioxidant balance in the rat.
2002 Mar-Apr
Effect of organophosphate intoxication on human serum paraoxonase.
2002 May
Paraoxonase Gln-Arg(192) and Leu-Met(55) gene polymorphisms and enzyme activity in a population with a low rate of coronary heart disease.
2002 May
Protein encapsulation in liposomes: efficiency depends on interactions between protein and phospholipid bilayer.
2002 May 10
Reactivation of immobilized acetyl cholinesterase in an amperometric biosensor for organophosphorus pesticide.
2002 May 20
Equipotent cholinesterase reactivation in vitro by the nerve agent antidotes HI 6 dichloride and HI 6 dimethanesulfonate.
2002 Oct
Convenient and rapid detection of pesticides in extracts of sheep wool.
2002 Sep
Cannabinoid CB1 receptor as a target for chlorpyrifos oxon and other organophosphorus pesticides.
2002 Sep 5
Lack of association between Alzheimer's disease and Gln-Arg 192 Q/R polymorphism of the PON-1 gene in an Italian population.
2003
Paraoxonase and susceptibility to organophosphorus poisoning in farmers dipping sheep.
2003 Feb
Evaluating reptile exposure to cholinesterase-inhibiting agrochemicals by serum butyrylcholinesterase activity.
2003 Feb
Layer-by-layer self-assembled chitosan/poly(thiophene-3-acetic acid) and organophosphorus hydrolase multilayers.
2003 Feb 19
Biochemical detection of esterases in the adult female integument of organophosphate-resistant Boophilus microplus (Acari: Ixodidae).
2003 Jan
Intravenous pyruvic acid application in minipigs partially protects acetylcholine-esteratic but not butyrylcholine-esteratic activity in plasma from inhibition by paraoxon.
2003 Jan-Feb
Influence of paraoxon (POX) and parathion (PAT) on apoptosis: a possible mechanism for toxicity in low-dose exposure.
2003 Jan-Feb
Flow injection amperometric detection of OP nerve agents based on an organophosphorus-hydrolase biosensor detector.
2003 Mar
Ghrelin can bind to a species of high density lipoprotein associated with paraoxonase.
2003 Mar 14

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Oral doses of 1.47 mg parathion/man/day produced no signs of toxicity in volunteers. Ingestion of 5.46 mg/kg/day produced moderatedepression of blood cholinesterase. A dosage of 0.07 mg/kg/day was regarded as the no-effect level in adults. (Parathion is metabolised in the human body to paraoxon). http://datasheets.scbt.com/sc-208151.pdf
Male Wistar rats received an intraperitoneal (i.p.) injection of one of three doses of paraoxon (0.3, 0.7, or 1mg/kg) or corn oil as vehicle (1ml/kg). he cortical glial glutamate transporters (GLAST and GLT-1) were up-regulated in animals treated with 0.7mg/kg of paraoxon, but down-regulated in 1mg/kg group. Neuronal glutamate transporter (EAAC1) was unchanged in 0.7mg/kg treated rats, while reduced in 1mg/kg group. No significant difference was found in the mRNA and protein expression of EAAC1 in animals intoxicated with 0.3mg/kg of paraoxon. Paraoxon (1mg/kg) resulted in an up-regulation of Bax and down-regulation of Bcl2 mRNA levels in the rat cerebral cortex.
Route of Administration: Intraperitoneal
Name Type Language
PARAOXON
HSDB   MART.   MI   WHO-DD  
Common Name English
E-600
Preferred Name English
E600
Code English
PARAOXON [MART.]
Common Name English
Paraoxon [WHO-DD]
Common Name English
PARAOXON [MI]
Common Name English
DIETHYL P-NITROPHENYL PHOSPHATE
Common Name English
PHOSPHACOL
Common Name English
PARAOXON [HSDB]
Common Name English
MIOTISAL
Common Name English
PARATHION OXYGEN ANALOG
Common Name English
NSC-404110
Code English
Classification Tree Code System Code
WHO-ATC S01EB10
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
WHO-VATC QS01EB10
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
NCI_THESAURUS C47792
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
NCI_THESAURUS C737
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
EPA PESTICIDE CODE 653502
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
Code System Code Type Description
DRUG CENTRAL
4683
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
FDA UNII
Q9CX8P80JW
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
MESH
D010261
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
PUBCHEM
9395
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-221-0
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
NSC
404110
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
WIKIPEDIA
PARAOXON
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
NCI_THESAURUS
C99562
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
CHEBI
27827
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
SMS_ID
100000182791
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
DRUG BANK
DB13495
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
EVMPD
SUB197081
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
ChEMBL
CHEMBL23838
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
MERCK INDEX
m8404
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID6024046
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
HSDB
6044
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY
CAS
311-45-5
Created by admin on Mon Mar 31 18:52:13 GMT 2025 , Edited by admin on Mon Mar 31 18:52:13 GMT 2025
PRIMARY