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

• ChemBase ID: 154364
• 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-/m0/s1
• InChIKey: GMHKMTDVRCWUDX-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 70989-04-7
• MDL Number: MFCD00270025
• PubChem SID: 24724646; 162248503
• PubChem CID: 107921

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; Ethyl Acetate
• Apperance: off-white solid; White Solid
• Melting Point: 135-138 °C; 137-138°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• 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

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H14N2O2

DETAILS

Sigma Aldrich - UC175

Biochem/physiol Actions
CYP2B6 & CYP2C19 substrate. Methenytoin isomer. Anticonvulsant; antiepileptic.

Toronto Research Chemicals - M225000

An anticonvulsant agent.

REFERENCES

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