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

• ChemBase ID: 155540
• Molecular Formular: C11H12N2O2
• Molecular Mass: 204.22518
• Monoisotopic Mass: 204.08987763
• SMILES: CC[C@@]1(C(=O)NC(=O)N1)c1ccccc1
• Canonical SMILES: CC[C@]1(NC(=O)NC1=O)c1ccccc1
• InChI: InChI=1S/C11H12N2O2/c1-2-11(8-6-4-3-5-7-8)9(14)12-10(15)13-11/h3-7H,2H2,1H3,(H2,12,13,14,15)/t11-/m0/s1
• InChIKey: UDTWZFJEMMUFLC-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 65567-34-2
• MDL Number: MFCD00272652
• PubChem SID: 162249678
• PubChem CID: 6540813

CALCULATED PROPERTIES

• Acid pKa: 9.824812
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.441477
• LogD (pH = 7.4): 1.439886
• Log P: 1.4414972
• Molar Refractivity: 54.6413 cm^3
• Polarizability: 21.230413 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Ethanol; Methanol
• Apperance: off-white; White to Off-White Solid
• Melting Point: 195-200°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: MU2452000
• 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

Product Information

• Empirical Formula (Hill Notation): C11H12N2O2

DETAILS

Sigma Aldrich - UC180

Biochem/physiol Actions
CYP2B6 metabolite of (R)-(-)-mephenytoin; anticonvulsant; hypnotic.

Toronto Research Chemicals - D292070

An anticonvulsant, hypnotic. A metabolite of Mephentoin.

REFERENCES

• Knabe, J., et al.: Arch. Phar., 313, 538 (1980)