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Details

Stereochemistry RACEMIC
Molecular Formula C11H12N2O2
Molecular Weight 204.2252
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHOTOIN

SMILES

CCN1C(=O)NC(C1=O)C2=CC=CC=C2

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

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PEGANONE

Cmax

ValueDoseCo-administeredAnalytePopulation
26.6 μg/mL
1000 mg single, oral
ETHOTOIN, (R)- plasma
Homo sapiens
30.4 μg/mL
1000 mg single, oral
ETHOTOIN, (S)- plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
510 μg × h/mL
1000 mg single, oral
ETHOTOIN, (R)- plasma
Homo sapiens
580 pg × h/mL
1000 mg single, oral
ETHOTOIN, (S)- plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5.11 h
25 mg/kg single, oral
ETHOTOIN serum
Homo sapiens
12.35 h
1000 mg single, oral
ETHOTOIN, (R)- plasma
Homo sapiens
12.28 h
1000 mg single, oral
ETHOTOIN, (S)- plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
58.8%
25 mg/kg single, oral
ETHOTOIN serum
Homo sapiens

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
PEGANONE (ethotoin tablets, USP) is administered orally in 4 to 6 divided doses daily. The drug should be taken after food, and doses should be spaced as evenly as practicable. Initial dosage should be conservative. For adults, the initial daily dose should be 1 g or less, with subsequent gradual dosage increases over a period of several days. The optimum dosage must be determined on the basis of individual response. The usual adult maintenance dose is 2 to 3 g daily. Less than 2 g daily has been found ineffective in most adults.
Route of Administration: Oral
In Vitro Use Guide
Ethotoin was not teratogenic at concentrations up to 2.93 mM in the sea urchin embryo