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Details

Stereochemistry RACEMIC
Molecular Formula C11H12N2O2
Molecular Weight 204.2256
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHOTOIN

SMILES

CCN1C(=O)C(c2ccccc2)N=C1O

InChI

InChIKey=SZQIFWWUIBRPBZ-UHFFFAOYSA-N
InChI=1S/C11H12N2O2/c1-2-13-10(14)9(12-11(13)15)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,12,15)

HIDE SMILES / InChI

Description
Curator's Comment:: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/010841s022lbl.pdf

Ethotoin is a hydantoin derivative and anticonvulsant. Ethotoin exerts an antiepileptic effect without causing general central nervous system depression. The mechanism of action is probably very similar to that of phenytoin. The latter drug appears to stabilize rather than to raise the normal seizure threshold, and to prevent the spread of seizure activity rather than to abolish the primary focus of seizure discharges. Ethotoin inhibits nerve impulses in the motor cortex by lowering sodium ion influx, limiting tetanic stimulation. Ethotoin is used for the control of tonic-clonic (grand mal) and complex partial (psychomotor) seizures. Ethotoin is marketed as Peganone by Ovation.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PEGANONE

Approved Use

PEGANONE (ethotoin tablets, USP) is indicated for the control of tonic-clonic (grand mal) and complex partial (psychomotor) seizures.

Launch Date

-400723200000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
26.6 μg/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHOTOIN, (R)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
30.4 μg/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHOTOIN, (S)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
510 μg × h/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHOTOIN, (R)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
580 pg × h/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHOTOIN, (S)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.35 h
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHOTOIN, (R)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5.11 h
25 mg/kg single, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHOTOIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
12.28 h
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHOTOIN, (S)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
58.8%
25 mg/kg single, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHOTOIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
strong
Drug as victimTox targets
PubMed

PubMed

TitleDatePubMed
Key structural features of ligands for activation of human pregnane X receptor.
2004 Apr
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Patents

Sample Use Guides

PEGANONE (ethotoin tablets, USP) is administered orally in 4 to 6 divided doses
Route of Administration: Oral
In Vitro Use Guide
Ethotoin was not teratogenic at concentrations up to 2.93 mM in the sea urchin embryo
Name Type Language
ETHOTOIN
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
ETHOTOIN [MART.]
Common Name English
ETHOTOIN [INN]
Common Name English
ETHOTOIN [JAN]
Common Name English
NSC-760074
Code English
ETHOTOIN [MI]
Common Name English
PEGANONE
Brand Name English
ETHOTOIN [HSDB]
Common Name English
ETHOTOIN [WHO-DD]
Common Name English
(+/-)-3-ETHYL-5-PHENYLHYDANTOIN
Systematic Name English
ETHOTOIN [USP MONOGRAPH]
Common Name English
ETHOTOIN [VANDF]
Common Name English
ETHOTOIN [ORANGE BOOK]
Common Name English
ETHOTOIN [USP-RS]
Common Name English
ACCENON
Brand Name English
2,4-IMIDAZOLIDINEDIONE, 3-ETHYL-5-PHENYL-, (+/-)-
Systematic Name English
Classification Tree Code System Code
WHO-ATC N03AB01
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
WHO-VATC QN03AB01
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
NDF-RT N0000008486
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
NDF-RT N0000175753
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
NCI_THESAURUS C264
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
Code System Code Type Description
CAS
86-35-1
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
USP_CATALOG
1264501
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY USP-RS
INN
660
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
EPA CompTox
86-35-1
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
DRUG BANK
DB00754
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
DRUG CENTRAL
1088
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
EVMPD
SUB07283MIG
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-665-1
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
PUBCHEM
3292
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
HSDB
3580
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
NCI_THESAURUS
C47524
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
RXCUI
4136
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL1095
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
FDA UNII
46QG38NC4U
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
WIKIPEDIA
ETHOTOIN
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY
MERCK INDEX
M5072
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY Merck Index
IUPHAR
7183
Created by admin on Fri Jun 25 20:32:09 UTC 2021 , Edited by admin on Fri Jun 25 20:32:09 UTC 2021
PRIMARY