(5R)-5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione

• ChemBase ID: 155098
• Molecular Formular: C12H14N2O2
• Molecular Mass: 218.25176
• Monoisotopic Mass: 218.1055277
• SMILES: CC[C@]1(C(=O)N(C(=O)N1)C)c1ccccc1
• Canonical SMILES: CC[C@@]1(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)/t12-/m1/s1
• InChIKey: GMHKMTDVRCWUDX-GFCCVEGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
• IUPAC Traditional name: (5R)-5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
• Synonyms: (R)-(-)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione; (R)-(-)-5-Ethyl-3-methyl-5-phenylhydantoin; (R)-(-)-Mephenytoin; (R)-Mephenytoin; (R)-5-Ethyl-3-methyl-5-phenylhydantoin; (-)-Mephenytoin; (5R)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione

Database IDs

• CAS Number: 71140-51-7
• MDL Number: MFCD00272651
• PubChem SID: 162249236
• PubChem CID: 119127

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Methanol
• Apperance: off-white; White Solid
• Melting Point: 137-138°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• 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

Product Information

• Empirical Formula (Hill Notation): C12H14N2O2

DETAILS

Sigma Aldrich - UC176

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

Toronto Research Chemicals - M224990

An anticonvulsant agent.

REFERENCES

• Shimada, et al.: Anal. Biochem., 147, 174 (1975)
• Dzhagatspanyan. IA., et al.: Pharm. Chem. J., 25, 181 (1975)