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Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.
recategorized from Nitrobenzenes to Nitrobenzene derivatives
 
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{{short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 402518942
| Watchedfields = changed
| IUPAC_name = diethyl 4-nitrophenyl phosphate
| verifiedrevid = 417767322
| image = Paraoxon.svg
| IUPAC_name = Diethyl 4-nitrophenyl phosphate
| CASNo_Ref = {{cascite|correct|CAS}}
| image = Paraoxon structure.svg
| width = 200px
| image2 = Paraoxon-3D-balls.png
| width2 = 170px
<!--Clinical data-->
| tradename =
| pregnancy_category =
| legal_status = Uncontrolled
| routes_of_administration =
<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 311-45-5
| ATC_prefix = S01
| ATC_suffix = EB10
| PubChem = 9395
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9026
| ChemSpiderID = 9026
| UNII_Ref = {{fdacite|changed|FDA}}
| InChI = 1/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
| UNII = Q9CX8P80JW
| InChIKey = WYMSBXTXOHUIGT-UHFFFAOYAD
| ChEBI_Ref = {{ebicite|changed|EBI}}
| smiles = [O-][N+](=O)c1ccc(OP(=O)(OCC)OCC)cc1
| ChEBI = 27827
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 23838
| ChEMBL = 23838
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D10529
<!--Chemical data-->
| C=10 | H=14 | N=1 | O=6 | P=1
| smiles = [O-][N+](=O)c1ccc(OP(=O)(OCC)OCC)cc1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WYMSBXTXOHUIGT-UHFFFAOYSA-N
| StdInChIKey = WYMSBXTXOHUIGT-UHFFFAOYSA-N
| CAS_number = 311-45-5
| ATC_prefix = S01
| ATC_suffix = EB10
| PubChem = 9395
| DrugBank =
| C=10|H=14|N=1|O=6|P=1
| molecular_weight = 275.195 g/mol
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| pregnancy_category=
| legal_status = Uncontrolled
| routes_of_administration =
}}
}}


'''Paraoxon''' is a [[parasympathomimetic]] which acts as an [[acetylcholinesterase inhibitor]]. It is an [[organophosphate]] [[Oxon (chemical)|oxon]], and the active [[metabolite]] of the insecticide [[parathion]]. It is also used as an [[opthalmological]] drug against [[glaucoma]]. 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. It is easily absorbed through skin, and was used as an assassination weapon by the apartheid-era South African chemical weapons program [[Project Coast]].<ref>[http://www.nti.org/e_research/profiles/SAfrica/Chemical/2440_3598.html NTI Country Overviews:South Africa:Chemical Capabilities:Paraoxon]</ref>
'''Paraoxon''' is a [[parasympathomimetic]] which acts as an [[cholinesterase inhibitor]]. It is an [[organophosphate]] [[Oxon (chemical)|oxon]], and the active [[metabolite]] of the insecticide [[parathion]]. It is also used as an [[ophthalmological]] drug against [[glaucoma]]. Paraoxon is one of the most potent acetylcholinesterase-inhibiting [[insecticide]]s 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. Paraoxon has been used by scientists to study acute and chronic effects of organophosphate intoxication.<ref>{{cite journal | vauthors = Deshpande LS, Carter DS, Phillips KF, Blair RE, DeLorenzo RJ | title = Development of status epilepticus, sustained calcium elevations and neuronal injury in a rat survival model of lethal paraoxon intoxication | journal = Neurotoxicology | volume = 44 | pages = 17–26 | date = September 2014 | pmid = 24785379 | pmc = 4176600 | doi = 10.1016/j.neuro.2014.04.006 }}</ref><ref>{{cite journal | vauthors = Deshpande LS, Phillips K, Huang B, DeLorenzo RJ | title = Chronic behavioral and cognitive deficits in a rat survival model of paraoxon toxicity | journal = Neurotoxicology | volume = 44 | pages = 352–7 | date = September 2014 | pmid = 25172410 | pmc = 4175062 | doi = 10.1016/j.neuro.2014.08.008 }}</ref> It is easily absorbed through skin, and was allegedly used as an [[assassination]] weapon by the apartheid-era [[South Africa]]n [[chemical weapon]]s program [[Project Coast]].<ref>[http://www.nti.org/e_research/profiles/SAfrica/Chemical/2440_3598.html NTI Country Overviews:South Africa:Chemical Capabilities:Paraoxon] {{webarchive|url=https://web.archive.org/web/20080708231705/http://www.nti.org/e_research/profiles/SAfrica/Chemical/2440_3598.html |date=2008-07-08 }}</ref>

== See also ==
*[[Armine (chemical)]]


== References ==
== References ==
{{Reflist|2}}
{{Reflist|2}}


{{Antiglaucoma_preparations_and_miotics}}
{{Opthalmologicals}}
{{Insecticides}}
{{Insecticides}}
{{Acetylcholine metabolism and transport modulators}}
{{Cholinergics}}


[[Category:Anticholinesterases]]
[[Category:Acetylcholinesterase inhibitors]]
[[Category:Organophosphates]]
[[Category:Organophosphates]]
[[Category:Nitrobenzenes]]
[[Category:Nitrobenzene derivatives]]
[[Category:Phenol esters]]
[[Category:Ethyl esters]]
[[Category:Ophthalmology drugs]]


{{Pharmacology-stub}}
{{Pharmacology-stub}}

[[cs:Paraoxon]]
[[de:Paraoxon]]
[[fr:Paraoxone]]
[[zh:對氧磷]]