ContaminantDB: Ethotoin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:35 UTC

Update Date

2026-04-04 15:32:38 UTC

Accession Number

CHEM002267

Identification

Common Name

Ethotoin

Class

Small Molecule

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 is no longer commonly used.

Contaminant Sources

HMDB Contaminants - Urine
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anticonvulsant
Drug
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-3-Ethyl-5-phenylhydantoin	ChEBI
1-Ethyl-2,5-dioxo-4-phenylimidazolidine	ChEBI
3-Ethyl-5-phenyl-2,4-imidazolidinedione	ChEBI
3-Ethyl-5-phenyl-imidazolidine-2,4-dione	ChEBI
3-Ethyl-5-phenylhydantoin	ChEBI
3-Ethyl-5-phenylimidazolidin-2,4-dione	ChEBI
Ethotoine	ChEBI
Ethotoinum	ChEBI
Etotoina	ChEBI
Accenon	Kegg
Peganone	Kegg
Abbott brand OF ethotoin	HMDB

Chemical Formula

C₁₁H₁₂N₂O₂

Average Molecular Mass

204.225 g/mol

Monoisotopic Mass

204.090 g/mol

CAS Registry Number

86-35-1

IUPAC Name

3-ethyl-5-phenylimidazolidine-2,4-dione

Traditional Name

ethotoin

SMILES

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

InChI Identifier

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)

InChI Key

SZQIFWWUIBRPBZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Phenylhydantoins

Alternative Parents

Substituents

5-phenylhydantoin
Phenylimidazolidine
Alpha-amino acid or derivatives
N-acyl urea
Ureide
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazolidine-2,4-dione (CHEBI:4888 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

anticonvulsant

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	94°C
Boiling Point	Not Available
Solubility	5280 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	2.38 g/L	ALOGPS
logP	1.11	ALOGPS
logP	1.07	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.29	ChemAxon
pKa (Strongest Basic)	-8.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.41 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.05 m³·mol⁻¹	ChemAxon
Polarizability	20.68 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-6980000000-86b5edde33787fa5b3d5	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0zfr-4920000000-137fae4223f8b51dd5cd	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0a4i-1190000000-3ade8f65bbabe08f852a	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-1190000000-56ad3615dcbc3fbecdbc	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-6980000000-86b5edde33787fa5b3d5	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0zfr-4920000000-137fae4223f8b51dd5cd	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0a4i-1190000000-3ade8f65bbabe08f852a	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-1190000000-56ad3615dcbc3fbecdbc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053f-4900000000-890da1feecbdd89e1320	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4i-1900000000-f71513d432cabc6ae596	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-1900000000-f71513d432cabc6ae596	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0690000000-2b14fabe2a8a38bfd87a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-2920000000-b4abc6e3540650b9fc2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-6900000000-ce4d6190e87bedc270a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0890000000-bc1ed1767185b47b35db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ugi-6930000000-d8856c4e6ba455c06408	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-8900000000-81cbbd6924131f65bccf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0390000000-d37f36d7d55fd839b005	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0apl-5930000000-d012a03e319c8a7a1e80	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0l06-9600000000-f553fba04ea2221422e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0290000000-0795d967a430c0f6e2ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f96-8910000000-a36978bebfc33440a272	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-f6e409587ccb41c14d58	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-6920000000-01714c9dcd6c4cf02362	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Fairly rapidly absorbed, however, the extent of oral absorption is not known.

Mechanism of Toxicity

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.

Metabolism

Hepatic. The drug exhibits saturable metabolism with respect to the formation of N-deethyl and p-hydroxyl-ethotoin, the major metabolites. Half Life: 3 to 9 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the control of tonic-clonic (grand mal) and complex partial (psychomotor) seizures.

Minimum Risk Level

Not Available

Health Effects

May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

Symptoms

Symptoms of overdose include drowsiness, loss of or impaired muscle coordination, nausea, visual disturbance, and, at very high doses, coma.

Treatment

Treatment should be begun by inducing emesis; gastric lavage may be considered as an alternative. General supportive measures will be necessary. A careful evaluation of blood-forming organs should be made following recovery. (2)

Concentrations

Not Available

External Links

DrugBank ID

DB00754

HMDB ID

HMDB0014892

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID