Pemoline

Identification

Summary

Pemoline is a central nervous system (CNS) stimulant that was previously used to treat attention deficit hyperactivity disorder (ADHD) and narcolepsy.

Generic Name
Pemoline
DrugBank Accession Number
DB01230
Background

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.

Type
Small Molecule
Groups
Approved, Illicit, Investigational, Withdrawn
Structure
Thumb
Weight
Average: 176.172
Monoisotopic: 176.05857751
Chemical Formula
C9H8N2O2
Synonyms
  • pemolina
  • Pemoline

Pharmacology

Indication

For treatment of Attention Deficit Hyperactivity Disorder (ADHD)

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Pemoline 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 action
Not Available
Absorption

Pemoline is rapidly absorbed from the gastrointestinal tract

Volume of distribution

Not Available

Protein binding

Approximately 50% (bound to plasma proteins).

Metabolism

Hepatic

Route of elimination

Pemoline is excreted primarily by the kidneys with approximately 50% excreted unchanged and only minor fractions present as metabolites.

Half-life

The serum half-life of pemoline is approximately 12 hours.

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Side effects include insomnia, anorexia, stomach ache, skin rashes, increased irritability, mild depression, nausea, dizziness, headache, drowsiness, and hallucinations

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
  • Avoid alcohol.
  • Limit caffeine intake.
  • Take with or without food. Food does not significantly affect absorption.

Products

Products2
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International/Other Brands
Betanamin / Ceractiv / Tradon
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CylertTablet37.5 mg/1OralPhysicians Total Care, Inc.1975-01-272004-10-31US flag
CylertTablet75 mg/1OralAbbvie1975-01-272008-04-30US flag
CylertTablet, chewable18.75 mg/1OralPhysicians Total Care, Inc.1996-01-052010-05-31US flag
CylertTablet37.5 mg/1OralAbbvie1975-01-272008-04-30US flag
CylertTablet75 mg/1OralPhysicians Total Care, Inc.1975-01-272004-10-31US flag
CylertTablet, chewable37.5 mg/1OralAbbvie1976-01-302008-04-30US flag
CylertTablet18.75 mg/1OralAbbvie1975-01-272008-04-30US flag

Categories

ATC Codes
N06BA05 — Pemoline
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
Oxazolines / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Imines / Hydrocarbon derivatives
Substituents
Aromatic heteromonocyclic compound / Azacycle / Hydrocarbon derivative / Imine / Monocyclic benzene moiety / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
1,3-oxazoles (CHEBI:7953)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
7GAQ2332NK
CAS number
2152-34-3
InChI Key
NRNCYVBFPDDJNE-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

References

General References
Not Available
KEGG Drug
D00744
KEGG Compound
C07899
PubChem Compound
4723
PubChem Substance
46509085
ChemSpider
4561
RxNav
7966
ChEBI
7953
ChEMBL
CHEMBL1177
PharmGKB
PA450836
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Pemoline
FDA label
Download (60.4 KB)
MSDS
Download (75 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentCocaine Related Disorders1
2WithdrawnTreatmentCocaine Related Disorders1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Dispensing Solutions
  • Mallinckrodt Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Physicians Total Care Inc.
  • Qualitest
  • Sandoz
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
TabletOral18.75 mg/1
TabletOral37.5 mg/1
TabletOral75 mg/1
Tablet, chewableOral18.75 mg/1
Tablet, chewableOral37.5 mg/1
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)256 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.7351
CYP450 2D6 inhibitorNon-inhibitor0.9412
CYP450 2C19 inhibitorNon-inhibitor0.7174
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-1900000000-6304707e673e5496a706

Drug created on June 13, 2005 13:24 / Updated on February 21, 2021 18:51