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
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
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
Title | Date | PubMed |
---|---|---|
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28603072
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
Edited
Fri Dec 15 17:46:28 GMT 2023
by
admin
on
Fri Dec 15 17:46:28 GMT 2023
|
Record UNII |
Q9CX8P80JW
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 |