5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione

• ChemBase ID: 139864
• Molecular Formular: C12H14N2O3
• Molecular Mass: 234.25116
• Monoisotopic Mass: 234.10044232
• SMILES: CCC1(C(=O)N(C(=O)N1)C)c1ccc(cc1)O
• Canonical SMILES: CCC1(NC(=O)N(C1=O)C)c1ccc(cc1)O
• InChI: InChI=1S/C12H14N2O3/c1-3-12(8-4-6-9(15)7-5-8)10(16)14(2)11(17)13-12/h4-7,15H,3H2,1-2H3,(H,13,17)
• InChIKey: OQPLORUDZLXXPD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione
• IUPAC Traditional name: 5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione
• Synonyms: (±)-5-Ethyl-5-(4-hydroxyphenyl)-3-methylhydantoin; (±)-5-Ethyl-5-(4-hydroxyphenyl)-3-methylimididazolidine-2,4-dione; 4-Hydroxymephenytoin; 5-Ethyl-5-(4-hydroxyphenyl)-3-methyl-2,4-imidazolidinedione; (+/-)-5-Ethyl-(4-hydroxyphenyl)-3-methylhydantoin; p-Hydroxymephenytoin; (+/-)-4-Hydroxy Mephenytoin; (±)-5-乙基-5-(4-羟苯基)-3-甲基海因; (±)-5-乙基-5-(4-羟苯基)-3-甲基羟基香豆素-2,4-二酮; 4-羟基美芬妥英

Database IDs

• CAS Number: 61837-65-8
• MDL Number: MFCD00142316
• PubChem SID: 24724640; 162234112; 24895460
• PubChem CID: 119507

CALCULATED PROPERTIES

• Acid pKa: 9.455566
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.3615601
• LogD (pH = 7.4): 1.3578259
• Log P: 1.3616079
• Molar Refractivity: 61.5189 cm^3
• Polarizability: 23.699648 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: >5 mg/mL; Ethyl Acetate
• Apperance: white; White Solid
• Melting Point: 152-153°C; 153-154 °C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Unknown
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H14N2O3

DETAILS

Sigma Aldrich - UC126

General description
CYP2C19 metabolite of mephenytoin.

Sigma Aldrich - H146

General description
CYP2C19 metabolite of mephenytoin.
Application
Pharmacological activity investigating:
• The drug effects on metabolization1
• In vitro cytochrome P450 activity in microsomes2Analyte for electron-capture gas chromatography procedures3

Toronto Research Chemicals - H944875

CYP2C19 metabolite of Mephenytoin.

REFERENCES

• Karlaganis, G., et al.: Drug Metab. Dispos., 8, 173 (1980)