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| Other names | 1-methylpyridine-6-carbaldehyde oxime |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
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| ECHA InfoCard | 100.027.080 |
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| Formula | C7H9N2O+ |
| Molar mass | 137.162 g·mol−1 |
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Pralidoxime (2-pyridine aldoxime methyl chloride) or2-PAM, usually as the chloride oriodide salts, belongs to a family of compounds calledoximes that bind toorganophosphate-inactivatedacetylcholinesterase.[1] It is used to treatorganophosphate poisoning[2] in conjunction withatropine and eitherdiazepam ormidazolam. It is a white solid.
Pralidoxime, 2-pyridinaldoxime methylchloride, is prepared by treatingpyridine-2-carboxaldehyde withhydroxylamine. The resulting pyridine-2-aldoxime is alkylated withmethyl iodide giving pralidoxime as the iodide salt.[3][4][5][6]
Pralidoxime is typically used in cases of organophosphate poisoning. Organophosphates such assarin bind to the hydroxy component (the esteric site) of the active site of theacetylcholinesterase enzyme, thereby blocking its activity. Pralidoxime binds to the other half (the unblocked, anionic site) of the active site and then displaces the phosphate from the serine residue. The conjoined poison / antidote then unbinds from the site, and thus regenerates the fully functional enzyme.
Some phosphate-acetylcholinesterase conjugates continue to react after the phosphate docks to the esteric site, evolving into a more recalcitrant state. This process is known as aging. Aged phosphate-acetylcholinesterase conjugate is resistant to antidotes such as pralidoxime. Pralidoxime is often used with atropine (a muscarinic antagonist) to help reduce the parasympathetic effects of organophosphate poisoning. Pralidoxime is only effective in organophosphate toxicity. It may have limited beneficial effects if the acetylcholinesterase enzyme is carbamylated, as occurs withneostigmine,pyridostigmine, or insecticides such ascarbaryl.
Pralidoxime has an important role in reversing paralysis of the respiratory muscles but due to its poor blood–brain barrier penetration, it has little effect on centrally-mediated respiratory depression. Atropine, which is choice of drug to antagonise the muscarinic effects of organophosphates, is administered even before pralidoxime during the treatment of organophosphate poisoning. While the efficacy of atropine has been well-established, clinical experience with pralidoxime has led to widespread doubt about its efficacy in treatment of organophosphorus poisoning.[7]
Intravenous infusions can lead to respiratory or cardiac arrest if given too quickly.[8]
When atropine and pralidoxime are used together, the signs of atropinization (flushing,mydriasis,tachycardia, dryness of the mouth and nose) may occur earlier than might be expected when atropine is used alone. This is especially true if the total dose of atropine has been large and the administration of pralidoxime has been delayed.
The following precautions should be kept in mind in the treatment of anticholinesterase poisoning, although they do not bear directly on the use of pralidoxime: sincebarbiturates are potentiated by the anticholinesterases, they should be used cautiously in the treatment of convulsions;morphine,theophylline,aminophylline,succinylcholine,reserpine, andphenothiazine-typetranquilizers should be avoided in patients with organophosphate poisoning.
There are no known absolute contraindications for the use of pralidoxime. Relative contraindications include known hypersensitivity to the drug and other situations in which the risk of its use clearly outweighs possible benefit.
