Pemoline


Pemoline
Pemoline
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 N
ATC code N06BA05
PubChem CID 4723
DrugBank APRD01169
ChemSpider 4561 YesY
UNII 7GAQ2332NK YesY
KEGG D00744 YesY
ChEMBL CHEMBL1177 YesY
Chemical data
Formula C9H8N2O2 
Mol. mass 176.172 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Pemoline was first synthesized in 1913[1] but it's activity was not discovered until the 1930s[2]. Under the names (Betanamin, Cylert, Tradon) it was used as a medication used 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. However, it can be legally prescribed in the US via the complex and rarely used "compassionate use / orphan drug" process by which a physician may complete extensive paper work on behalf of a single patient to obtain an "investigational new drug application" that allows importation and prescription of the compound on a case by case basis for up to one year and subject to renewal.

Contents

Mechanism of action

Similar to methylphenidate, the mechanism of action of pemoline is to inhibit the reuptake of dopamine and to increase the levels of dopamine and norepinephrine in the central nervous system.[citation needed] Pemoline has some advantages over other stimulants in that it does not reduce the appetite or cause dry mouth. Dependence has only rarely been reported.[4]

Interactions

Methylphenidate may enhance the liver toxicity of pemoline.[5]

Hepatotoxicity and discontinuation

In some patients pemoline is suspected of causing hepatotoxicity,[5] so the FDA recommended that regular liver tests should be performed on those treated with it.[6] Since receiving FDA approval in 1975,[7] it has been linked with 21 cases of liver failure, of which 13 resulted in liver replacement or death. Although the medication was used by an estimated 10,000 Americans (mostly for narcolepsy or attention deficit disorder), in 2005 the Food and Drug Administration (FDA) withdrew approval for pemoline due to pressure from public advocacy groups, notably Public Citizen. Dr. Peter Lurie, deputy director of Public Citizen, had demanded that FDA summarily ban Cylert and its generic versions claiming that at least 193 children had suffered serious hepatic consequences. Under this pressure but despite the lack of evidence of serious adverse events among adults, the agency sent a letter to Abbott Laboratories (Cylert brand owner) stating that marketing of pemoline could continue "if and only if a good faith effort is made on your part to collect the data necessary" to measure the drug's risks. In March 2005, Abbott discontinued production of Cylert, citing economic reasons.

An analogue of aminorex, 4-methylaminorex has appeared as a black market drug with abuse potential similar to methamphetamine.

Overdose

Overdose of pemoline may present with choreoathetosis symptoms.[8]

See also

References

  1. ^ Chemische Berichte,1913,vol.46, p. 2083
  2. ^ Acta Academiae Aboensis, Series B: Mathematica et Physica, 1939, vol. 11, #14 p. 3,7
  3. ^ Annual Estimates Of Requirements Of Narcotic Drugs, Manufacture Of Synthetic Drugs, Opium Production And Cultivation Of The
  4. ^ Bonnet U, Davids E (September 2006). "A rare case of dependence on pemoline". Prog. Neuropsychopharmacol. Biol. Psychiatry 30 (7): 1340–1. doi:10.1016/j.pnpbp.2006.02.017. PMID 16600453. http://linkinghub.elsevier.com/retrieve/pii/S0278-5846(06)00078-9. 
  5. ^ a b 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. http://linkinghub.elsevier.com/retrieve/pii/S002234769800208X. 
  6. ^ 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. http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=0890-8567&volume=41&issue=7&spage=785. 
  7. ^ 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. 
  8. ^ 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. 

External links


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Look at other dictionaries:

  • pemoline — noun Etymology: origin unknown Date: 1961 a synthetic drug C9H8N2O2 that is a mild stimulant of the central nervous system …   New Collegiate Dictionary

  • pemoline — /pem euh leen , lin/, n. Pharm. a synthetic, weak, central nervous system stimulant, C9H8N2O2, with sympathomimetic activity, used as an adjunct in the management of hyperkinetic behavior disorders. [1960 65; perh. p(h)e(nyl) + (i)m(ino) +… …   Universalium

  • pemoline — noun A medication used to treat ADHD and narcolepsy, having similar action to methylphenidate …   Wiktionary

  • pemoline — A psychostimulant used in the treatment of attention deficit disorder (hyperactivity) in children. * * * pem·o·line pem ə .lēn n a synthetic drug C9H8N2O2 that is a mild stimulant of the central nervous system and has been used to treat attention …   Medical dictionary

  • pemoline — pem·o·line …   English syllables

  • pemoline —  n.f. Psychostimulant …   Le dictionnaire des mots absents des autres dictionnaires

  • pemoline — ˈpeməˌlēn, lə̇n noun ( s) Etymology: perhaps from phenyl + imino + oxazolidinone, a derivative of oxazolidine, from oxazolidine + one : a synthetic drug C9H8N2O2 that is a mild stimulant of the central nervous system …   Useful english dictionary

  • magnesium pemoline — magnesium pemoline, a combination of the stimulant pemoline and magnesium hydroxide, used as a drug to stimulate the nervous system …   Useful english dictionary

  • Пемолин (Pemoline) — слабый стимулятор нервной системы; применяется для лечения гиперкинетического синдрома у детей. Назначается внутрь. Возможные побочные эффекты: головная боль, раздражительность, головокружение, повышенное потоотделение, потеря аппетита,… …   Медицинские термины

  • ПЕМОЛИН — (pemoline) слабый стимулятор нервной системы; применяется для лечения гиперкинетического синдрома у детей. Назначается внутрь. Возможные побочные эффекты: головная боль, раздражительность, головокружение, повышенное потоотделение, потеря аппетита …   Толковый словарь по медицине