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

• ChemBase ID: 414
• Molecular Formular: C12H14N2O2
• Molecular Mass: 218.25176
• Monoisotopic Mass: 218.1055277
• SMILES: O=C1N(C(=O)NC1(CC)c1ccccc1)C
• Canonical SMILES: CCC1(NC(=O)N(C1=O)C)c1ccccc1
• InChI: InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)
• InChIKey: GMHKMTDVRCWUDX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
• IUPAC Traditional name: @mephenytoin; mephenytoin
• Brand Name: Epiazin; Gerot-Epilan; Insulton; Mesdontoin; Mesontoin; Methoin; Metydan; Phenantoin; Sacerno; Sedantional; Sedantoin; Sedantoinal; Triantoin
• Synonyms: Mephentoin; Methyl Hydantoin; Methylphenetoin; Mephenytoin; (±)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione; (±)-5-Ethyl-3-methyl-5-phenylhydantoin; (±)-Mephenytoin

Database IDs

• CAS Number: 50-12-4
• EC Number: 200-012-8
• MDL Number: MFCD00022407
• PubChem SID: 46508677; 160963877
• PubChem CID: 4060
• ATC CODE: N03AB04
• CHEMBL: 861
• Chemspider ID: 3920
• DrugBank ID: DB00532
• KEGG ID: D00375
• Unique Ingredient Identifier: R420KW629U
• Wikipedia Title: Mephenytoin
• Medline Plus: a611020

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.179447
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.6651723
• LogD (pH = 7.4): 1.665102
• Log P: 1.6651733
• Molar Refractivity: 59.538 cm^3
• Polarizability: 23.067186 Å^3
• Polar Surface Area: 49.41 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.64
• LOG S: -2.35
• Solubility (Water): 9.70e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1270 mg/L
• Apperance: off-white
• Melting Point: 115-118 °C; 135-137 °C
• Hydrophobicity(logP): 1.3

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 7 hours
• Pregnancy Category: C (US)

Product Information

• Empirical Formula (Hill Notation): C12H14N2O2

DETAILS

DrugBank - DB00532

• Drug Groups: approved
• Description: Mephenytoin is a hydantoin-derivative anticonvulsant used to control various partial seizures. It is generally reserved for treatment of individuals refractory to less toxic agents. Mephenytoin and oxazolidinedione derivatives are associated with higher incidences of blood dyscrasias compared to other anticonvulsants. As such, these agents should not be used concurrently.
• Indication: For the treatment of refractory partial epilepsy.
• Pharmacology: Mephenytoin is an antiepileptic drug which can be useful in the treatment of epilepsy. The primary site of action appears to be the motor cortex where spread of seizure activity is inhibited. Possibly by promoting sodium efflux from neurons, mephenytoin tends to stabilize the threshold against hyperexcitability caused by excessive stimulation or environmental changes capable of reducing membrane sodium gradient. This includes the reduction of posttetanic potentiation at synapses. Loss of posttetanic potentiation prevents cortical seizure foci from detonating adjacent cortical areas. Mephenytoin reduces the maximal activity of brain stem centers responsible for the tonic phase of tonic-clonic (grand mal) seizures.
• Affected Organisms: Humans and other mammals
• Half Life: Approximately 7 hours
• Distribution: * 1.4 L/kg
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - UC177

Biochem/physiol Actions
CYP2B6 and CYP2C19 substrate; anticonvulsive, antiepileptic.