Pemoline

Pemoline
Clinical data
Trade namesCylert, others
Other namesPheniminooxazolidinone; Phenylisohydantoin; Phenylpseudohydantoin; Phenilone; 2-Imino-5-phenyl-4-oxazolidinone; 2-Amino-5-phenyl-1,3-oxazol-4(5H)-one
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		By mouth[1][2]
Drug classStimulant;
Dopamine reuptake inhibitor;
Dopamine releasing agent
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class B1 (Psychoactive drugs)[3]
  • CA: Schedule IV
  • DE: Prescription only (Anlage III for higher doses)
  • US: Schedule IV
Pharmacokinetic data
Protein binding≤50%[2][1]
MetabolismLiver[2]
MetabolitesVarious[2]
Elimination half-life7–12 hours[1][2]
ExcretionMainly urine[2]
Identifiers
IUPAC name
  • (RS)-2-amino-5-phenyl-1,3-oxazol-4(5H)-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.016.763
Chemical and physical data
FormulaC9H8N2O2
Molar mass176.175 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • O=C2\N=C(/OC2c1ccccc1)N
InChI
  • InChI=1S/C9H8N2O2/c10-9-11-8(12)7(13-9)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12) Y
  • Key:NRNCYVBFPDDJNE-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Pemoline, formerly sold under the brand name Cylert among others, is a stimulant medication which was used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy,[2]- it has since been discontinued in most countries due to rare but serious liver toxicity.[4][5] The medication was taken by mouth.[2]

Common side effects include insomnia, decreased appetite, abdominal pain, irritability, and headaches,[1][2] while rare cases of serious liver damage requiring liver transplantation or causing death have been reported.[6][7] As a stimulant, Pemoline acts as a selective dopamine reuptake inhibitor and releasing agent[1][8][2][9] via indirect agonism of dopamine receptors.[10] In addition, it shows little activity with respect to norepinephrine, thus minimal to no cardiovascular or sympathomimetic effects in comparison to many other stimulants.[1][8][2]

Pemoline was first synthesized in 1913, but its stimulant activity was not discovered until the 1930s, nor used for ADHD until 1975.[11][12][1] Between 1997 and 2005, many countries, including the United States, withdrew the drug due to liver toxicity.[13][7][14] However, it remains available in Japan for the treatment of narcolepsy at lower doses than those used for ADHD.[5] Pemoline is a schedule IV controlled substance in the United States due to structural and functional similarity to other stimulants, and potential for misuse.[15][16] but is noted to have less misuse potential than other stimulant drugs.[1]

  1. ^ a b c d e f g h Cite error: The named reference PatrickMarkowitz1997 was invoked but never defined (see the help page).
  2. ^ a b c d e f g h i j k Cite error: The named reference Cylert-Label was invoked but never defined (see the help page).
  3. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  4. ^ Billiard M (June 2008). "Narcolepsy: current treatment options and future approaches". Neuropsychiatr Dis Treat. 4 (3): 557–66. PMC 2526380. PMID 18830438.
  5. ^ a b Shader RI (April 2017). "Risk Evaluation and Mitigation Strategies (REMS), Pemoline, and What Is a Signal?". Clin Ther. 39 (4): 665–669. doi:10.1016/j.clinthera.2017.03.008. PMID 28366595.
  6. ^ Nakamura H, Blumer JL, Reed MD (March 2002). "Pemoline ingestion in children: a report of five cases and review of the literature". J Clin Pharmacol. 42 (3): 275–82. doi:10.1177/00912700222011292. PMID 11865963. S2CID 27024140.
  7. ^ a b Safer DJ, Zito JM, Gardner JE (June 2001). "Pemoline hepatotoxicity and postmarketing surveillance". J Am Acad Child Adolesc Psychiatry. 40 (6): 622–9. doi:10.1097/00004583-200106000-00006. PMID 11392339.
  8. ^ a b Cite error: The named reference pmid9185233 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Fuller_1978 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference pmid9708845 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference ChemischeBerichte1913 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference ActaAcademiaeAboensis1939 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference pmid18793403 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference pmid18217792 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference INCB was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference CRC2014 was invoked but never defined (see the help page).
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