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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Groupsillicit, withdrawn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
SaltsNot Available
Brand names
NameCompany
BetanaminNot Available
CeractivNot Available
CylertNot Available
TradonNot Available
Brand mixtures
Brand NameIngredients
Bebia Ointment PommadeMagnesium Pemoline + Magnesium Silicate + Zinc Oxide
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassNot Available
Direct parentBenzene and Substituted Derivatives
Alternative parentsPolyamines; Carboxylic Acid Amides
Substituentscarboxamide group; carboxylic acid derivative; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzene and substituted derivatives. These are aromatic compounds containing at least one benzene ring.
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
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.983
Caco-2 permeable - 0.5064
P-glycoprotein substrate Non-substrate 0.8719
P-glycoprotein inhibitor I Non-inhibitor 0.9072
P-glycoprotein inhibitor II Non-inhibitor 0.8851
Renal organic cation transporter Non-inhibitor 0.8843
CYP450 2C9 substrate Non-substrate 0.7857
CYP450 2D6 substrate Non-substrate 0.7793
CYP450 3A4 substrate Non-substrate 0.6888
CYP450 1A2 substrate Inhibitor 0.5472
CYP450 2C9 substrate Non-inhibitor 0.7351
CYP450 2D6 substrate Non-inhibitor 0.9412
CYP450 2C19 substrate Non-inhibitor 0.7174
CYP450 3A4 substrate Non-inhibitor 0.973
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8905
Ames test Non AMES toxic 0.5921
Carcinogenicity Non-carcinogens 0.8633
Biodegradation Not ready biodegradable 0.8753
Rat acute toxicity 2.5744 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9818
hERG inhibition (predictor II) Non-inhibitor 0.9594
Pharmacoeconomics
Manufacturers
  • Abbott laboratories pharmaceutical products div
  • Actavis totowa llc
  • Teva pharmaceuticals usa
  • Mallinckrodt inc
  • Sandoz inc
  • Vintage pharmaceuticals inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
TabletOral
Tablet, chewableOral
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point256 dec °CPhysProp
logP0.7Not Available
Predicted Properties
PropertyValueSource
water solubility9.79e-01 g/lALOGPS
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 area64.68ChemAxon
rotatable bond count1ChemAxon
refractivity45.7ChemAxon
polarizability17.04ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00744
KEGG CompoundC07899
PubChem Compound4723
PubChem Substance46509085
ChemSpider4561
PharmGKBPA450836
Drug Product Database397520
RxListhttp://www.rxlist.com/cgi/generic/pemoline.htm
Drugs.comhttp://www.drugs.com/mtm/pemoline.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cyl1109.shtml
WikipediaPemoline
ATC CodesN06BA05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelshow(60.4 KB)
MSDSshow(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