Physostigmine
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Physostigmine
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| Systematic (IUPAC) name | |
| (3aR,8aS)- 1,3a,8-trimethyl- 1H,2H,3H,3aH,8H,8aH- pyrrolo [2,3-b] indol-5-yl N-methylcarbamate | |
| Identifiers | |
| CAS number | 57-47-6 |
| ATC code | S01EB05 V03 |
| PubChem | 5983 |
| DrugBank | APRD00406 |
| ChemSpider | 5763 |
| Chemical data | |
| Formula | C15H21N3O2 |
| Mol. mass | 275.346 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | Major metabolite: Eseroline |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
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| Legal status | |
| Routes | ? |
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Physostigmine (also known as eserine from éséré, West African name for the Calabar bean) is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor alkaloid of the Calabar bean.
The chemical was synthesized for the first time in 1935 by the chemists Percy Lavon Julian and Josef Pikl. It is available in the U.S. under the trade names Antilirium, Eserine Salicylate, Isopto Eserine, and Eserine Sulfate.
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[edit] Mechanism
By interfering with the metabolism of acetylcholine, physostigmine indirectly stimulates both nicotinic and muscarinic receptors.
[edit] Clinical uses
Physostigmine is used to treat myasthenia gravis, glaucoma, Alzheimer's disease and delayed gastric emptying. It has been shown to improve the short term memory (Krus et al. 1968). Recently, it has begun to be used in the treatment of orthostatic hypotension.
Because it is a tertiary amine (and thus does not hydrogen bond, making it more hydrophobic), it can cross the blood-brain barrier, and physostigmine salicylate is used to treat the central nervous system effects of atropine, scopolamine and other anticholinergic drug overdoses.
Physostigmine is the antidote of choice for datura stramonium poisoning. It is also an antidote for atropa belladonna poisoning, the same as for atropine.[1] It has been also used as an antidote for poisoning with GHB as well,[2] but is poorly effective and often causes additional toxicity, so is not a recommended treatment.[3]
[edit] Side effects
An overdose can cause cholinergic syndrome.
Other side effects may include nausea, vomiting, diarrhea, anorexia, dizziness, headache, stomach pain, sweating and dyspepsia.[4]
[edit] References
- ^ Potter, Samuel O.L. (1893). A Handbook of Materia Medica Pharmacy and Therapeutics. London: P. Blakiston's. pp. 53. http://books.google.com/books?id=q2ku1dbnaLYC&pg=PA53&dq=the+antidote+for+belladonna+is+physostigmine+or+pilocarpine+the+same+as+for+atropine&ei=F5PAR6a0KofCtAPa_ty2CA.
- ^ Traub, SJ; Nelson; Hoffman (2002). "Physostigmine as a treatment for gamma-hydroxybutyrate toxicity: a review". Journal of toxicology. Clinical toxicology 40 (6): 781–7. doi:. PMID 12475191.
- ^ Zvosec, D.; Smith, S.; Litonjua, R.; Westfal, R. (2007). "Physostigmine for gamma-hydroxybutyrate coma: inefficacy, adverse events, and review". Clinical toxicology (Philadelphia, Pa.) 45 (3): 261–265. doi:. PMID 17453877.
- ^ Alzheimer Research Forum
- 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
- Krus, D.J. et al. (1968). Learning and memory of chronic alcoholics influenced by cholinotropic drugs. Activ nerv. Super., 10, 420-421.
- This article incorporates text from the Encyclopædia Britannica, Eleventh Edition, a publication now in the public domain.
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