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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

Molecular Formula C10H14NO6P
Molecular Weight 275.195
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Carboxylesterase: specificity and spontaneous reactivation of an endogenous scavenger for organophosphorus compounds.
2001 Dec
Peripheral site ligands accelerate inhibition of acetylcholinesterase by neutral organophosphates.
2001 Dec
Species- and substrate-specific stimulation of human plasma paraoxonase 1 (PON1) activity by high chloride concentration.
2002
Sensitive detection of organophosphorus pesticides using a needle type amperometric acetylcholinesterase-based bioelectrode. Thiocholine electrochemistry and immobilised enzyme inhibition.
2002 Apr
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
Comparative inhibition kinetics for acetylcholinesterases extracted from organophosphate resistant and susceptible strains of Boophilus microplus (Acari: Ixodidae).
2002 Dec
Synthesis and stability study of a modified phenylpropionic acid linker-based esterase-sensitive prodrug.
2002 Dec 2
Rapid assessment of organophosphorous/carbamate exposure in the bivalve mollusc Mytilus edulis using combined esterase activities as biomarkers.
2002 Dec 3
Validation of different commercially available cholinesterases for pesticide toxicity test.
2002 Jan-Feb
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
Characterization of butyrylcholinesterase antagonism of cocaine-induced hyperactivity.
2002 Jun
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
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
Paraoxonase1-192 polymorphism modulates the effects of regular and acute exercise on paraoxonase1 activity.
2002 May
Human and rodent carboxylesterases: immunorelatedness, overlapping substrate specificity, differential sensitivity to serine enzyme inhibitors, and tumor-related expression.
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
Paraoxonase 1 activity: a new vascular marker of dementia?
2002 Nov
Lizard cholinesterases as biomarkers of pesticide exposure: enzymological characterization.
2002 Nov
An approach for the quantitative consideration of genetic polymorphism data in chemical risk assessment: examples with warfarin and parathion.
2002 Nov
In vitro stability and in vivo pharmacokinetic studies of a model opioid peptide, H-Tyr-D-Ala-Gly-Phe-D-Leu-OH (DADLE), and its cyclic prodrugs.
2002 Nov
Equipotent cholinesterase reactivation in vitro by the nerve agent antidotes HI 6 dichloride and HI 6 dimethanesulfonate.
2002 Oct
[Reactivation and aging of acetylcholinesterase in human brain inhibited by phoxim and phoxim oxon in vitro].
2002 Sep
Detection of organophosphorus insecticides with immobilized acetylcholinesterase - comparative study of two enzyme sensors.
2002 Sep
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
Coordination number of zinc ions in the phosphotriesterase active site by molecular dynamics and quantum mechanics.
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
Use of atropine-treated Daphnia magna survival for detection of environmental contamination by acetylcholinesterase inhibitors.
2003 Jan
Effects of chronic dermal exposure to nonlethal doses of methyl parathion on brain regional acetylcholinesterase and muscarinic cholinergic receptors in female rats.
2003 Jan 1
Thermally triggered purification and immobilization of elastin-OPH fusions.
2003 Jan 5
Paraoxonase (PON 1) as a biomarker of susceptibility for organophosphate toxicity.
2003 Jan-Feb
In vitro protection of plasma cholinesterases by metoclopramide from inhibition by paraoxon.
2003 Jan-Feb
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
Detection of pesticides using an amperometric biosensor based on ferophthalocyanine chemically modified carbon paste electrode and immobilized bienzymatic system.
2003 Mar
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:46:28 GMT 2023
Edited
by admin
on Fri Dec 15 17:46:28 GMT 2023
Record UNII
Q9CX8P80JW
Record Status Validated (UNII)
Record Version
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Name Type Language
PARAOXON
HSDB   MART.   MI   WHO-DD  
Common Name English
E-600
Code 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 Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
WHO-VATC QS01EB10
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
NCI_THESAURUS C47792
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
NCI_THESAURUS C737
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
EPA PESTICIDE CODE 653502
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
Code System Code Type Description
DRUG CENTRAL
4683
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
FDA UNII
Q9CX8P80JW
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
MESH
D010261
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
PUBCHEM
9395
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-221-0
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
NSC
404110
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
WIKIPEDIA
PARAOXON
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
NCI_THESAURUS
C99562
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
CHEBI
27827
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
SMS_ID
100000182791
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
DRUG BANK
DB13495
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
EVMPD
SUB197081
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL23838
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
MERCK INDEX
m8404
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID6024046
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
HSDB
6044
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
CAS
311-45-5
Created by admin on Fri Dec 15 17:46:28 GMT 2023 , Edited by admin on Fri Dec 15 17:46:28 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE