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
Drug classStimulant;
Dopamine reuptake inhibitor;
Dopamine releasing agent
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding≤50%
MetabolismLiver
MetabolitesVarious
Elimination half-life7–12 hours
ExcretionMainly urine
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
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) 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,- it has since been discontinued in most countries due to rare but serious liver toxicity. The medication was taken by mouth.

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

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