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

• ChemBase ID: 634
• Molecular Formular: C11H12N2O2
• Molecular Mass: 204.22518
• Monoisotopic Mass: 204.08987763
• SMILES: O=C1N(C(=O)NC1c1ccccc1)CC
• Canonical SMILES: CCN1C(=O)NC(C1=O)c1ccccc1
• InChI: 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)
• InChIKey: SZQIFWWUIBRPBZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethyl-5-phenylimidazolidine-2,4-dione
• IUPAC Traditional name: 3-ethyl-5-phenylhydantoin; ethotoin
• Brand Name: Accenon; Peganone; Pegoanone
• Synonyms: Ethotoine [INN-French]; Ethotoinum [INN-Latin]; Etotoina [INN-Spanish]; Ethotoin

Database IDs

• CAS Number: 86-35-1
• PubChem SID: 160964097; 46504521
• PubChem CID: 3292
• CHEBI ID: 4888
• ATC CODE: N03AB01
• CHEMBL: 1095
• Chemspider ID: 3176
• DrugBank ID: DB00754
• KEGG ID: D00708
• Unique Ingredient Identifier: 46QG38NC4U
• Wikipedia Title: Ethotoin
• Medline Plus: a682022

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.288526
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0666922
• LogD (pH = 7.4): 1.0666375
• Log P: 1.066693
• Molar Refractivity: 55.0493 cm^3
• Polarizability: 21.230879 Å^3
• Polar Surface Area: 49.41 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.11
• LOG S: -1.93
• Solubility (Water): 2.38e+00 g/l

PROPERTIES

Physical Property

• Solubility: 5280 mg/L
• Hydrophobicity(logP): 0.8

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 3 to 9 hours
• Pregnancy Category: C

DETAILS

DrugBank - DB00754

• Drug Groups: approved
• 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.
• Indication: For the control of tonic-clonic (grand mal) and complex partial (psychomotor) seizures.
• Pharmacology: 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.
• Toxicity: Symptoms of overdose include drowsiness, loss of or impaired muscle coordination, nausea, visual disturbance, and, at very high doses, coma.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. The drug exhibits saturable metabolism with respect to the formation of N-deethyl and p-hydroxyl-ethotoin, the major metabolites.
• Absorption: Fairly rapidly absorbed, however, the extent of oral absorption is not known.
• Half Life: 3 to 9 hours
• References: SCHWADE ED, RICHARDS RK, EVERETT GM: Peganone, a new antiepileptic drug. Dis Nerv Syst. 1956 May;17(5):155-8. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• SCHWADE ED, RICHARDS RK, EVERETT GM: Peganone, a new antiepileptic drug. Dis Nerv Syst. 1956 May;17(5):155-8. Pubmed