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Identification
NamePemoline
Accession NumberDB01230  (APRD01169)
TypeSmall Molecule
GroupsIllicit, Withdrawn
Description

In 2005, the Food and Drug Administration (FDA) withdrew approval for pemoline. In March 2005, Abbott Laboratories (Cylert marketer) had discontinued the production of Cylert arguing economic reasons.

Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
BetanaminNot Available
CeractivNot Available
CylertNot Available
TradonNot Available
Brand mixtures
Brand NameIngredients
Bebia Ointment PommadeMagnesium Pemoline + Magnesium Silicate + Zinc Oxide
SaltsNot Available
CategoriesNot Available
CAS number2152-34-3
WeightAverage: 176.172
Monoisotopic: 176.05857751
Chemical FormulaC9H8N2O2
InChI KeyNRNCYVBFPDDJNE-UHFFFAOYSA-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)
IUPAC Name
2-amino-5-phenyl-4,5-dihydro-1,3-oxazol-4-one
SMILES
NC1=NC(=O)C(O1)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • N-acylimine
  • Isourea
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor treatment of Attention Deficit Hyperactivity Disorder (ADHD)
PharmacodynamicsPemoline belongs to the group of medicines called central nervous system (CNS) stimulants. It is used to treat attention deficit hyperactivity disorder (ADHD). Pemoline stimulates the brain, probably by affecting neurotransmitters, the chemicals in the brain that nerves use to communicate with each other.
Mechanism of actionNot Available
AbsorptionPemoline is rapidly absorbed from the gastrointestinal tract
Volume of distributionNot Available
Protein bindingApproximately 50% (bound to plasma proteins).
Metabolism

Hepatic

Route of eliminationPemoline is excreted primarily by the kidneys with approximately 50% excreted unchanged and only minor fractions present as metabolites.
Half lifeThe serum half-life of pemoline is approximately 12 hours.
ClearanceNot Available
ToxicitySide effects include insomnia, anorexia, stomach ache, skin rashes, increased irritability, mild depression, nausea, dizziness, headache, drowsiness, and hallucinations
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.983
Caco-2 permeable-0.5064
P-glycoprotein substrateNon-substrate0.8719
P-glycoprotein inhibitor INon-inhibitor0.9072
P-glycoprotein inhibitor IINon-inhibitor0.8851
Renal organic cation transporterNon-inhibitor0.8843
CYP450 2C9 substrateNon-substrate0.7857
CYP450 2D6 substrateNon-substrate0.7793
CYP450 3A4 substrateNon-substrate0.6888
CYP450 1A2 substrateInhibitor0.5472
CYP450 2C9 substrateNon-inhibitor0.7351
CYP450 2D6 substrateNon-inhibitor0.9412
CYP450 2C19 substrateNon-inhibitor0.7174
CYP450 3A4 substrateNon-inhibitor0.973
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8905
Ames testNon AMES toxic0.5921
CarcinogenicityNon-carcinogens0.8633
BiodegradationNot ready biodegradable0.8753
Rat acute toxicity2.5744 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9818
hERG inhibition (predictor II)Non-inhibitor0.9594
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point256 dec °CPhysProp
logP0.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.979 mg/mLALOGPS
logP0.52ALOGPS
logP0.8ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)14.95ChemAxon
pKa (Strongest Basic)0.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.68 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.7 m3·mol-1ChemAxon
Polarizability17.04 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (60.4 KB)
MSDSDownload (75 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13