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		Oral[1][2]
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding≤50%[2][1]
MetabolismLiver[2]
MetabolitesVarious[2]
Elimination half-life7–12 hours[1][2]
ExcretionMainly urine[2]
Identifiers
  • (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 Edit this at Wikidata
Chemical and physical data
FormulaC9H8N2O2
Molar mass176.175 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O=C2\N=C(/OC2c1ccccc1)N
  • 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) checkY
  • Key:NRNCYVBFPDDJNE-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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

Side effects of pemoline include insomnia, decreased appetite, abdominal pain, irritability, and headaches.[1][2] Rarely, the medication can cause serious liver damage, and this can result in liver transplantation or death.[6][7] Pemoline is a psychostimulant and acts as a selective dopamine reuptake inhibitor and releasing agent.[1][8][2][9] Hence, it functions as an indirect agonist of dopamine receptors.[10] Pemoline has little effect on norepinephrine and hence has minimal or no cardiovascular or sympathomimetic effects, in contrast to many other stimulants.[1][8][2]

Pemoline was synthesized in 1913 but was not discovered to be a stimulant until the 1930s and was not used in the treatment of ADHD until 1975.[11][12][1] It was withdrawn due to liver toxicity in many countries between 1997 and 2005, including the United States.[13][7][14] However, it remains available in Japan for the treatment of narcolepsy at lower doses than used for ADHD.[5] Pemoline is a schedule IV controlled substance in the United States due to its relation to other stimulants and a potential for misuse.[15][16] It seems to have less misuse potential than other stimulants.[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).