Structure via PubChem · Public domain (PubChem)
pemoline
Sign in to saveAlso known as Cylert, phenylisohydantoin, pheniminooxazolidinone, phenylpseudohydantoin, 2-imino-5-phenyl-4-oxazolidinone, 2-imino-4-keto-5-phenyltetrahydrooxazole, 2-Amino-5-phenyl-4(5H)-oxazolone, 5-phenylisohydantion
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.
Key facts
- Drug.Verifiedfields
- changed
- Drug.class
- Stimulant; Dopamine reuptake inhibitor; Dopamine releasing agent
- Drug.verifiedrevid
- 461086403
- Drug.IUPAC_name
- (RS)-2-amino-5-phenyl-1,3-oxazol-4(5H)-one
- Drug.image
- Pemoline structure 2.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 175px
- Drug.image2
- File:Pemoline ball-and-stick model.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 175px
- Drug.chirality
- Racemic mixture
- Drug.tradename
- Cylert, others
- Drug.pregnancy_US
- B
- Drug.legal_AU
- S4
- Drug.legal_BR
- B1
- Drug.legal_CA
- Schedule IV
- Drug.legal_DE
- Rx-only/Anlage III
- Drug.legal_US
- Schedule IV
via Wikipedia infobox
Chemical data
- Formula
- C9H8N2O2
- Molecular weight
- 176.17 g/mol
- IUPAC name
- 2-imino-5-phenyl-1,3-oxazolidin-4-one
- SMILES
- C1=CC=C(C=C1)C2C(=O)NC(=N)O2
- InChIKey
- NRNCYVBFPDDJNE-UHFFFAOYSA-N
- XLogP
- 1.2
- Polar surface area
- 62.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
570 papers- Pemoline hepatotoxicity in children.The Journal of pediatrics · 1998
- Pemoline-associated fulminant liver failure: testing the evidence for causation.Clinical pharmacology and therapeutics · 1995
- Pemoline-associated hepatic failure: a critical analysis of the literature.Pediatric neurology · 1997
- Pemoline in ADHD.Journal of the American Academy of Child and Adolescent Psychiatry · 1997
- Pemoline induced acute choreoathetosis: case report and review of the literature.Journal of toxicology. Clinical toxicology · 1997
via PubMed
Wikidata facts
- Mass
- 176.059
Show 5 more facts
- chemical formula
- C₉H₈N₂O₂
- canonical SMILES
- C1=CC=C(C=C1)C2C(=O)N=C(O2)N
- World Health Organisation international non-proprietary name
- pemoline
- defined daily dose
- 40
- Commons category
- Pemoline
via Wikidata · CC0
~10 min read
Article
18 sectionsContents
- Medical uses
- Available forms
- Side effects
- Liver toxicity
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Names
- Availability
- Legal status
- Research
- Fatigue
- References
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.