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{{drugbox
{{Refimprove|date=July 2009}}
| IUPAC_name       = 1,1'-[oxybis(methylene)]bis{4-[(''E'')-<br>(hydroxyimino)methyl]pyridinium}
{{Drugbox
| image             = Obidoxime skeletal.svg
| Verifiedfields = changed
| CAS_number        = 114-90-9
| verifiedrevid = 462263966
| ATC_prefix        = V03
| IUPAC_name = 1,1'-[oxybis(methylene)]bis{4-[(''E'')-<br>(hydroxyimino)methyl]pyridinium}
| ATC_suffix        = AB13
| image = Obidoxime.png
| PubChem          = 5485192
 
| DrugBank          =
<!--Clinical data-->
| C = 14 | H = 16 | N = 4 | O = 3 | charge = +2
| tradename =   
| molecular_weight = 288.302 g/mol
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| bioavailability  =
| pregnancy_US = <!-- A / B            / C / D / X -->
| protein_bound    =
| pregnancy_category =   
| metabolism        =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| elimination_half-life =
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| excretion        = [[Kidney|Renal]]
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| pregnancy_US     = <!-- A / B            / C / D / X -->
| legal_status =
| pregnancy_category=   
| routes_of_administration =
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
 
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
<!--Pharmacokinetic data-->
| legal_UK         = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| bioavailability = 
| legal_US         = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| protein_bound = 
| legal_status     =  
| metabolism = 
| routes_of_administration =  
| elimination_half-life = 
| excretion = [[Kidney|Renal]]
 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 114-90-9
| ATC_prefix = V03
| ATC_suffix = AB13
| PubChem = 5485192
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4588647
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = N6KNE1QA9O
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 291233
 
<!--Chemical data-->
| C=14 | H=16 | N=4 | O=3 | charge = +2
| molecular_weight = 288.302 g/mol
| smiles = O=[NH+]\C=C1\C=C/N(/C=C1)COCN/2/C=C\C(C=C\2)=C\[NH+]=O
| InChI = 1/C14H14N4O3/c19-15-9-13-1-5-17(6-2-13)11-21-12-18-7-3-14(4-8-18)10-16-20/h1-10H,11-12H2/p+2
| InChIKey = HIGRLDNHDGYWQJ-SKRXCDHZAW
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H14N4O3/c19-15-9-13-1-5-17(6-2-13)11-21-12-18-7-3-14(4-8-18)10-16-20/h1-10H,11-12H2/p+2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HIGRLDNHDGYWQJ-UHFFFAOYSA-P
}}
}}
'''Obidoxime''' is a member of the [[oxime]] family used to treat [[nerve gas]] poisoning. Oximes are drugs known for their ability to reverse the binding of [[organophosphorus]] compounds to the enzyme [[acetylcholinesterase]] (AChE).  
__NOTOC__
 
{{SI}}
 
{{CMG}}
 
==Overview==
'''Obidoxime''' is a member of the [[oxime]] family used to treat [[nerve gas]] poisoning. Oximes are drugs known for their ability to reverse the binding of [[organophosphorus]] compounds to the enzyme [[acetylcholinesterase]] (AChE).<ref name="pmid19519385">{{cite journal |author=Jokanović M, Prostran M |title=Pyridinium oximes as cholinesterase reactivators. Structure-activity relationship and efficacy in the treatment of poisoning with organophosphorus compounds |journal=Curr. Med. Chem. |volume=16 |issue=17 |pages=2177–88 |year=2009 |pmid=19519385 |doi= 10.2174/092986709788612729|url=http://www.bentham-direct.org/pages/content.php?CMC/2009/00000016/00000017/0004C.SGM}}</ref>


AChE is an enzyme that removes [[acetylcholine]] from the [[synapse]] after it creates the required stimulation on the next [[nerve cell]]. If it gets inhibited, acetylcholine is not removed after the stimulation and multiple stimulations are made, resulting in muscle contractions and [[paralysis]].  
AChE is an enzyme that removes [[acetylcholine]] from the [[synapse]] after it creates the required stimulation on the next [[nerve cell]]. If it gets inhibited, acetylcholine is not removed after the stimulation and multiple stimulations are made, resulting in muscle contractions and [[paralysis]].  


[[Organophosphate]]s (such as nerve gases) are well known inhibitors of AChE. They bind to a specific place on the enzyme and prevent it from functioning normally by changing the [[Hydroxyl|OH group]] on the [[serine]] residue and by [[proton]]ating (quaternary [[nitrogen]], R<sub>4</sub>N<sup>+</sup>) the nearby nitrogen atom located in the [[histidine]] residue.
[[Organophosphate]]s (such as nerve gases) are well-known inhibitors of AChE. They bind to a specific place on the enzyme and prevent it from functioning normally by changing the [[Hydroxyl|OH group]] on the [[serine]] residue and by [[proton]]ating (quaternary [[nitrogen]], R<sub>4</sub>N<sup>+</sup>) the nearby nitrogen atom located in the [[histidine]] residue.


==Function==
==Function==
Oximes such as obidoxime, [[pralidoxime]] and [[asoxime]] (HI-6) are used to restore enzyme functionality. They have greater affinity for the organic phosphate residue than the enzyme and they remove the phosphate group, restore the OH to serine and turn nitrogen from histidine back into its R<sub>3</sub>N form (tertiary nitrogen). This results in full enzyme recovery and the phosphate-oxime compound is eliminated from the organism via [[urine]].
Oximes such as obidoxime, [[pralidoxime]] and [[asoxime]] (HI-6) are used to restore enzyme functionality. They have greater affinity for the organic phosphate residue than the enzyme and they remove the phosphate group, restore the OH to serine and turn nitrogen from histidine back into its R<sub>3</sub>N form (tertiary nitrogen). This results in full enzyme recovery and the phosphate-oxime compound is eliminated from the organism via [[urine]].


==Side effects==
==Side effects==
Oximes like these do have side effects and they include [[liver]] damage, [[kidney]] damage, [[nausea]], [[vomiting]], but they are very efficient [[antidote]]s to nerve gas poisoning. Usually treatment of poisoning includes the use of [[atropine]], which can slow down the action of the poison, giving more time to apply the oxime.


Oximes like these do have side effects and they include [[liver]] damage, [[kidney]] damage, [[nausea]], [[vomit]]ing, but they are very efficient [[antidote]]s to nerve gas poisoning. Usually treatment of poisoning includes the use of [[atropine]], which can slow down the action of the poison, giving more time to apply the oxime.
==References==
{{Reflist|2}}


==Nerve gas development==
In the past ten years various [[army|armies]] of the world have been developing nerve gases that are resistant to oximes. The best known gases of this generation are the [[Russia]]n [[Novichok]] gases. They already possess the oxime group, twice [[halogen]]ated and are resistant to known oximes.


{{Antidotes}}
{{Antidotes}}


[[Category:Antidotes]]
[[Category:Antidotes]]
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[[Category:Oximes]]
 
[[Category:Quaternary ammonium compounds]]
 
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Revision as of 18:44, 9 April 2015

Obidoxime
Clinical data
ATC code
Pharmacokinetic data
ExcretionRenal
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC14H16N4O3+2
Molar mass288.302 g/mol
3D model (JSmol)
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Obidoxime is a member of the oxime family used to treat nerve gas poisoning. Oximes are drugs known for their ability to reverse the binding of organophosphorus compounds to the enzyme acetylcholinesterase (AChE).[1]

AChE is an enzyme that removes acetylcholine from the synapse after it creates the required stimulation on the next nerve cell. If it gets inhibited, acetylcholine is not removed after the stimulation and multiple stimulations are made, resulting in muscle contractions and paralysis.

Organophosphates (such as nerve gases) are well-known inhibitors of AChE. They bind to a specific place on the enzyme and prevent it from functioning normally by changing the OH group on the serine residue and by protonating (quaternary nitrogen, R4N+) the nearby nitrogen atom located in the histidine residue.

Function

Oximes such as obidoxime, pralidoxime and asoxime (HI-6) are used to restore enzyme functionality. They have greater affinity for the organic phosphate residue than the enzyme and they remove the phosphate group, restore the OH to serine and turn nitrogen from histidine back into its R3N form (tertiary nitrogen). This results in full enzyme recovery and the phosphate-oxime compound is eliminated from the organism via urine.

Side effects

Oximes like these do have side effects and they include liver damage, kidney damage, nausea, vomiting, but they are very efficient antidotes to nerve gas poisoning. Usually treatment of poisoning includes the use of atropine, which can slow down the action of the poison, giving more time to apply the oxime.

References

  1. ↑ Jokanović M, Prostran M (2009). "Pyridinium oximes as cholinesterase reactivators. Structure-activity relationship and efficacy in the treatment of poisoning with organophosphorus compounds". Curr. Med. Chem. 16 (17): 2177–88. doi:10.2174/092986709788612729. PMID 19519385.


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