Pemoline

Identification

Name
Pemoline
Accession Number
DB01230  (APRD01169)
Type
Small Molecule
Groups
Approved, Illicit, Investigational, Withdrawn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
Synonyms
Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CylertTablet18.75 mg/1OralAbbvie1975-01-272008-04-30Us
CylertTablet37.5 mg/1OralPhysicians Total Care, Inc.1975-01-272004-10-31Us
CylertTablet75 mg/1OralAbbvie1975-01-272008-04-30Us
CylertTablet, chewable18.75 mg/1OralPhysicians Total Care, Inc.1996-01-052010-05-31Us
CylertTablet37.5 mg/1OralAbbvie1975-01-272008-04-30Us
CylertTablet75 mg/1OralPhysicians Total Care, Inc.1975-01-272004-10-31Us
CylertTablet, chewable37.5 mg/1OralAbbvie1976-01-302008-04-30Us
International/Other Brands
Betanamin / Ceractiv / Cylert / Tradon
Categories
UNII
7GAQ2332NK
CAS number
2152-34-3
Weight
Average: 176.172
Monoisotopic: 176.05857751
Chemical Formula
C9H8N2O2
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

Pharmacology

Indication

For treatment of Attention Deficit Hyperactivity Disorder (ADHD)

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
Toxicity

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

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
  • Avoid high doses of caffeine.
  • Take without regard to meals. Avoid alcohol.

References

General References
Not Available
External Links
KEGG Drug
D00744
KEGG Compound
C07899
PubChem Compound
4723
PubChem Substance
46509085
ChemSpider
4561
ChEBI
7953
ChEMBL
CHEMBL1177
PharmGKB
PA450836
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Pemoline
ATC Codes
N06BA05 — 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

Taxonomy

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
Monocyclic benzene moiety / Oxazoline / Oxacycle / Azacycle / Organoheterocyclic compound / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
1,3-oxazoles (CHEBI:7953)

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:01