U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C9H8N2O2
Molecular Weight 176.172
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PEMOLINE

SMILES

NC1=NC(=O)C(O1)C2=CC=CC=C2

InChI

InChIKey=NRNCYVBFPDDJNE-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description

Pemoline is a central nervous system stimulant. Pemoline is structurally dissimilar to the amphetamines and methylphenidate. Pemoline is generally considered dopaminergic, but its precise method of action hasn't yet been definitively determined. The interaction of pemoline with other drugs has not been studied in humans. The following are adverse reactions in decreasing order of severity within each category associated with pemoline: hepatic dysfunction, aplastic anemia, convulsive seizures, hallucinations, insomnia, anorexia and weight loss.

CNS Activity

Originator

Traube, W.
1
Curator's Comment: Pemoline was first synthesized in 1913 but its activity was not discovered until the 1930s.

Approval Year

1975
63
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
CYLERT

Approved Use

CYLERT (pemoline) is indicated in Attention Deficit Hyperactivity Disorder (ADHD). Because of its association with life threatening hepatic failure, CYLERT should not ordinarily be considered as first line therapy for ADHD.

Launch Date

1975
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.76 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/4017397/
2 mg/kg single, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PEMOLINE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
46.2 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/4017397/
2 mg/kg single, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PEMOLINE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.28 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/4017397/
2 mg/kg single, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PEMOLINE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
150 mg 1 times / day steady, oral
Highest studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11176767
unhealthy
n = 11
Health Status: unhealthy
Condition: human immunodeficiency virus disease
Sex: M+F
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/11176767
Sources:
https://pubmed.ncbi.nlm.nih.gov/11176767
37.5 mg 1 times / day steady, oral (starting)
Recommended
Dose: 37.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 37.5 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/016832s022_017703s018lbl.pdf
unhealthy
Health Status: unhealthy
Condition: Attention Deficit Hyperactivity Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/016832s022_017703s018lbl.pdf
Other AEs: Hepatic failure...
Other AEs:
Hepatic failure (grade 5)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/016832s022_017703s018lbl.pdf
96 mg 1 times / day steady, oral (mean)
Dose: 96 mg, 1 times / day
Route: oral
Route: steady
Dose: 96 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11176767
unhealthy
n = 45
Health Status: unhealthy
Condition: human immunodeficiency virus disease
Sex: M+F
Population Size: 45
Sources:
https://pubmed.ncbi.nlm.nih.gov/11176767
Disc. AE: Neuropathic pain...
AEs leading to
discontinuation/dose reduction:
Neuropathic pain (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11176767
AEs

AEs

AESignificanceDosePopulation
Hepatic failure grade 5
37.5 mg 1 times / day steady, oral (starting)
Recommended
Dose: 37.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 37.5 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/016832s022_017703s018lbl.pdf
unhealthy
Health Status: unhealthy
Condition: Attention Deficit Hyperactivity Disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/016832s022_017703s018lbl.pdf
Neuropathic pain 1 patient
Disc. AE
96 mg 1 times / day steady, oral (mean)
Dose: 96 mg, 1 times / day
Route: oral
Route: steady
Dose: 96 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11176767
unhealthy
n = 45
Health Status: unhealthy
Condition: human immunodeficiency virus disease
Sex: M+F
Population Size: 45
Sources:
https://pubmed.ncbi.nlm.nih.gov/11176767
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:7953
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7953
eMolecules
1988428
https://www.emolecules.com/cgi-bin/more?vid=1988428
eMolecules
2733323
https://www.emolecules.com/cgi-bin/more?vid=2733323
PubMed

PubMed

TitleDatePubMed
Gilles de la Tourette's disorder associated with pemoline.
1980 Dec
Pemoline-induced Tourette's disorder: a case report.
1981 Aug
Pemoline-induced chorea.
1981 Mar
Stimulant medications precipitate Tourette's syndrome.
1982 Mar 26
Chorea in long-term use of pemoline.
1983 Feb
Depression following pemoline withdrawal in a hyperactive child.
1985 Mar
Evidence of lack of abuse or dependence following pemoline treatment: results of a retrospective survey.
1986 Jun
Pemoline-induced choreoathetosis and rhabdomyolysis.
1988 Jan-Dec
Pemoline-induced abnormal involuntary movements.
1989 Apr
Change from Mg-pemoline to bupropion in a 12-year-old boy with attention-deficit hyperactivity disorder.
1990 Oct
Stuttering and stimulants.
1991 Feb
Tics and dyskinesias associated with stimulant treatment in attention-deficit hyperactivity disorder.
1994 Aug
Pemoline-associated fulminant liver failure: testing the evidence for causation.
1995 Jun
Pemoline induced acute choreoathetosis: case report and review of the literature.
1997
Four cases of severe hepatotoxicity associated with pemoline: possible autoimmune pathogenesis.
1998 May
Adverse drug reaction. Pemoline and dyskinesia.
1999 Feb
Severe hypotension in a patient receiving pemoline during general anesthesia.
2000 Nov
Emergence of tics in children with attention deficit hyperactivity disorder treated with stimulant medications.
2001 May-Jun
Inappropriate pemoline therapy leading to acute liver failure and liver transplantation.
2002 Jun
Self-injurious behaviour: a comparison of caffeine and pemoline models in rats.
2004 Dec
A surveillance method for the early identification of idiosyncratic adverse drug reactions.
2008
Individual differences in vulnerability for self-injurious behavior: studies using an animal model.
2011 Feb 2
Patents

Patents

CA2271197A1
1
EP0948490A1
1
US5677463
1
WO1998022450 A1
1

Sample Use Guides

In Vivo Use Guide
Starting dose is 37.5 mg/day Daily dose should be gradually increased by 18.75 mg at one week intervals The effective daily dose for most patients will range from 56.25 to 75 mg Maximum recommended daily dose is 112.5 mg.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
PEMOLINE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
2-AMINO-5-PHENYL-1,3-OXAZOL-4(5H)-ONE
Systematic Name English
PEMOLINE [JAN]
Common Name English
PEMOLIN
Common Name English
CENTRAMIN
Brand Name English
YH-1
Code English
5-PHENYL-2-IMINOOXAZOLIDIN-4-ONE
Systematic Name English
AZOXODON
Brand Name English
STIMULOL
Brand Name English
CYLERT
Brand Name English
PEMOLINE [MART.]
Common Name English
4(5H)-OXAZOLONE, 2-AMINO-5-PHENYL-
Systematic Name English
HYTON ASA
Common Name English
TRADONE
Common Name English
NSC-25159
Code English
PIOXOL
Brand Name English
PEMOLINE [ORANGE BOOK]
Common Name English
VOLITAL
Common Name English
STIMUL
Common Name English
SIGMADYN
Brand Name English
AZOKSODON
Brand Name English
OKODON
Brand Name English
2-OXAZOLIN-4-ONE, 2-AMINO-5-PHENYL-
Systematic Name English
AZOXODONE
Brand Name English
DELTAMIN
Brand Name English
SENIOR
Common Name English
PONDEX
Common Name English
2-AMINO-5-PHENYL-2-OXAZOLIN-4-ONE
Systematic Name English
DELTAMINE
Common Name English
PEMOLINE [MI]
Common Name English
4-OXAZOLIDINONE, 2-IMINO-5-PHENYL-
Systematic Name English
KETHAMED
Brand Name English
2-IMINO-4-KETO-5-PHENYLTETRAHYDROOXAZOLE
Systematic Name English
LA-956
Code English
PHENYLPSEUDOHYDANTOIN
Common Name English
PEMOLINE [HSDB]
Common Name English
PHENIMINOOXAZOLIDINONE
Common Name English
PHENYLISOHYDANTOIN
Common Name English
RONYL
Common Name English
FENOXAZOL
Brand Name English
PHENOXAZOLE
Common Name English
5-PHENYL-2-IMINO-4-OXOOXAZOLIDINE
Systematic Name English
PEMOLINE [VANDF]
Common Name English
2-AMINO-5-PHENYL-4(5H)-OXAZOLONE
Systematic Name English
PIO
Common Name English
TRADON
Common Name English
PEMOLINE [USAN]
Common Name English
HYTON
Common Name English
pemoline [INN]
Common Name English
2-Imino-5-phenyl-4-oxazolidinone
Systematic Name English
2-IMINO-4-OXO-5-PHENYLOXAZOLIDINE
Systematic Name English
Pemoline [WHO-DD]
Common Name English
NSC-169499
Code English
SISTRA
Common Name English
NITAN
Common Name English
DANTROMIN
Brand Name English
Classification Tree Code System Code
LIVERTOX 750
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
WHO-VATC QN06BA05
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
DEA NO. 1530
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
WHO-ATC N06BA05
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
NCI_THESAURUS C47795
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
Code System Code Type Description
EVMPD
SUB09657MIG
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID3023427
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
MERCK INDEX
m8458
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C47655
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
MESH
D010389
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
CAS
2933-45-1
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
SUPERSEDED
CAS
2152-34-3
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
DRUG BANK
DB01230
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
RXCUI
7966
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY RxNorm
HSDB
3148
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
INN
1054
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
CAS
101053-01-4
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
SUPERSEDED
WIKIPEDIA
PEMOLINE
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
SMS_ID
100000082496
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
ChEMBL
CHEMBL1177
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
DRUG CENTRAL
2075
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
PUBCHEM
4723
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
CHEBI
7953
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
NSC
169499
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
NSC
25159
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
ECHA (EC/EINECS)
218-438-8
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
FDA UNII
7GAQ2332NK
Created by admin on Sat Dec 16 16:44:44 GMT 2023 , Edited by admin on Sat Dec 16 16:44:44 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of PEMOLINE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966