Pemoline
From Wikipedia, the free encyclopedia
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| Systematic (IUPAC) name | |
| (RS)-2-amino-5-phenyl-1,3-oxazol-4(5H)-one | |
| Clinical data | |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| Pregnancy cat. | B U.S. |
| Legal status | Schedule IV (United States) Schedule IV (Canada) Lista II (Argentina) |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | 50% bound to plasma proteins |
| Metabolism | Hepatic |
| Half-life | 12 hours |
| Excretion | ? |
| Identifiers | |
| CAS number | 2152-34-3  |
| ATC code | N06BA05 |
| PubChem | CID 4723 |
| DrugBank | DB01230 |
| ChemSpider | 4561  |
| UNII | 7GAQ2332NK |
| KEGG | D00744 |
| ChEMBL | CHEMBL1177 |
| Chemical data | |
| Formula | C9H8N2O2 |
| Mol. mass | 176.172 g/mol |
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Pemoline is a stimulant drug of the oxazoline class. It was first synthesized in 1913[1] but its activity was not discovered until the 1930s.[2] Under the names Betanamin, Cylert, Tradon, and Ceractiv it was used as a medication to treat attention-deficit hyperactivity disorder (ADHD) and narcolepsy. Under the Convention on Psychotropic Substances, it is a Schedule IV drug.[3] It is no longer generally available in the United States. Pemoline magnesium, a chelate between pemoline and magnesium, displays certain pharmacological advantages over pemoline. The compound is the monohydrate of an equimolar mixture between pemoline and magnesium hydroxide. The absorption of pemoline magnesium is more rapid and the duration of action is extended, and the effect is more reliable.
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[edit] Mechanism of action
Unlike other psychostimulants which are dopaminergic, pemoline is thought to be dopamimetic in nature. Pemoline passes the blood–brain barrier and acts as a surrogate for dopamine, not affecting endogenous intracellular dopamine. For this reason, and the fact that it has little or no affinity for adrenaline receptors, pemoline has minimal sympathomimetic side effects such as: dry mouth, reduction in appetite, high blood pressure, increased heart rate, constriction of smooth muscle, cardiac stress, dilated pupils and insomnia. There is some data to suggest that pemoline is a nootropic acting as a catalyst conductor in the synapses of the brain's memory centers, raising the efficiency of memory and assisting RNA formation in the brain. While drugs like dexamphetamine and methylphenidate are classified as Schedule II, pemoline is listed as Schedule IV (non-narcotic). In studies conducted on primates, pemoline fails to demonstrate a potential for self-administration.
[edit] Interactions
Other stimulants and MAOI’s are contraindicated with pemoline.
[edit] Liver toxicity
In some patients pemoline is suspected of causing hepatotoxicity,[4] so the FDA recommended that regular liver tests should be performed on those treated with it.[5] Since receiving FDA approval in 1975,[6] it has been linked with 21 cases of liver failure, of which 13 resulted in liver replacement or death.
In March 2005 Abbott Laboratories and generic manufacturers withdrew pemoline from the market due to concerns about the liver toxicity risk.[7]
[edit] Overdose
Overdose of pemoline may present with choreoathetosis symptoms.[8]
[edit] See also
[edit] Notes
- ^ Chemische Berichte,1913,vol.46, p. 2083
- ^ Acta Academiae Aboensis, Series B: Mathematica et Physica, 1939, vol. 11, #14 p. 3,7
- ^ Annual Estimates Of Requirements Of Narcotic Drugs, Manufacture Of Synthetic Drugs, Opium Production And Cultivation Of The
- ^ Marotta PJ, Roberts EA (May 1998). "Pemoline hepatotoxicity in children". J. Pediatr. 132 (5): 894–7. doi:10.1016/S0022-3476(98)70329-4. PMID 9602211.
- ^ Willy ME, Manda B, Shatin D, Drinkard CR, Graham DJ (July 2002). "A study of compliance with FDA recommendations for pemoline (Cylert)". J Am Acad Child Adolesc Psychiatry 41 (7): 785–90. doi:10.1097/00004583-200207000-00009. PMID 12108802.
- ^ Etwel FA, Rieder MJ, Bend JR, Koren G (2008). "A surveillance method for the early identification of idiosyncratic adverse drug reactions". Drug Saf 31 (2): 169–80. doi:10.2165/00002018-200831020-00006. PMID 18217792.
- ^ "Pemoline - Withdrawn due to liver toxicity risk". WHO Pharmaceuticals Newsletter (05). 2005.
- ^ Stork CM, Cantor R (1997). "Pemoline induced acute choreoathetosis: case report and review of the literature". J. Toxicol. Clin. Toxicol. 35 (1): 105–8. doi:10.3109/15563659709001175. PMID 9022662.
[edit] Additional references
- Budavari, S (Ed.) (1996). The Merck Index. An encyclopedia of chemicals, drugs, and biologicals (12 ed.). Whitehouse Station: Merck Research Laboratories ISBN 0-911910-12-3
- Michanie, Claudio: Diferencias del Trastorno por Déficit de Atención en el niño y el adulto: consideraciones diagnósticas y terapéuticas. En Julio Moizeszowicz (Ed.): Psicofarmacología Psicodinámica IV - Actualizaciones 2004 ISBN 987-43-8089-6
- Moizeszowicz, Julio: Psicofarmacología psicodinámica IV, Editorial Paidós, Buenos Aires (2000) ISBN 950-12-3180-1
- Wilens T et al.: The Stimulants. Psychiatric Clinics of North America, 1992; 15: 191-222.
[edit] External links
- Pemoline monograph at HealthyPlace.com
- AScribe Newswire press release about the withdrawal.
- Pemoline (patient information)
- Cylert Discontinued Press Release
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