Neostigmine
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| Neostigmine
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| Systematic (IUPAC) name | |
| 3-(dimethylcarbamoyloxy)-N,N,N-trimethylbenzenaminium | |
| Identifiers | |
| CAS number | |
| ATC code | N07 S01EB06 |
| PubChem | |
| Chemical data | |
| Formula | C12H19N2O2 |
| Mol. mass | 223.294 g/mol |
| Pharmacokinetic data | |
| Bioavailability | Unclear, probably less than 5% |
| Metabolism | Slow hydrolysis by acetylcholinesterase and also by plasma esterases |
| Half life | 50-90 minutes |
| Excretion | Unchanged drug (up to 70%) and alcoholic metabolite (30%) are excreted in the urine |
| Therapeutic considerations | |
| Pregnancy cat. |
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| Legal status | |
| Routes | ? |
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Neostigmine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor. By interfering with the breakdown of acetylcholine, neostigmine indirectly stimulates both nicotinic and muscarinic receptors. It does cross the blood-brain barrier albeit poorly. Neostigmine binds to the anionic site of cholinesterase. The drug blocks the active site of acetylcholinesterase so the enzyme can no longer break down the acetylcholine molecules before they reach the postsynaptic membrane receptors. This allows for the threshold to be reached so a new impulse can be triggered in the next neuron. In myasthenia gravis there are too few acetylcholine receptors so with the acetylcholinesterase blocked, acetylcholine can bind to the few receptors and trigger a muscular contraction.
Clinical Uses
It is used to improve muscle tone in people with myasthenia gravis and routinely, in anesthesia at the end of an operation, to reverse the effects of non-depolarizing muscle relaxants such as vecuronium.
It can also be used for urinary retention resulting from general anaesthetia and to treat curariform drug toxicity.
Another indication for use is the Ogilvie syndrome which is a pseudoobstruction of the colon in critically ill patients.
Neostigmine will cause slowing of the heart rate (bradycardia), for this reason it is usually given along with a parasympatholytic drug such as atropine or glycopyrrolate.
Neostigmine is available under several trade names such as Prostigmin®.
Neostigmine was first synthesized by Aeschlimann and Reinert in 1931.
Sources
- Brenner, G. M. (2000). Pharmacology. Philadelphia, PA: W.B. Saunders Company. ISBN 0-7216-7757-6
- Canadian Pharmacists Association (2000). Compendium of Pharmaceuticals and Specialties (25th ed.). Toronto, ON: Webcom. ISBN 0-919115-76-4
Parasympathomimetics (N07A) | |
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| Anticholinesterases | Stigmine (Neostigmine, Pyridostigmine, Distigmine) - Ambenonium |
| Choline esters | Carbachol - Bethanechol |
| Other parasympathomimetics | Pilocarpine - Choline alfoscerate |
Anticholinesterases (N06DA, N07AA) | |
|---|---|
| Carbamates | Ambenonium - Demecarium - Stigmine (Neostigmine, Physostigmine, Pyridostigmine, Rivastigmine) |
| Other | Galantamine - Metrifonate - Donepezil - Tacrine - Edrophonium |
Ophthalmologicals: antiglaucoma preparations and miotics (S01E) | |
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| Sympathomimetics | Apraclonidine • Brimonidine • Clonidine • Dipivefrine • Epinephrine |
| Parasympathomimetics | Aceclidine • Acetylcholine • Carbachol • Demecarium • Echothiophate • Stigmine (Fluostigmine, Neostigmine, Physostigmine) • Paraoxon • Pilocarpine |
| Carbonic anhydrase inhibitors | Acetazolamide • Brinzolamide • Diclofenamide • Dorzolamide • Methazolamide |
| Beta blocking agents | Befunolol • Betaxolol • Carteolol • Levobunolol • Metipranolol • Timolol |
| Prostaglandin analogues | Bimatoprost • Latanoprost • Travoprost • Unoprostone |
| Other agents | Dapiprazole • Guanethidine |
fr:Néostigmine ja:ネオスチグミンit:neostigmina
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
