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

• ChemBase ID: 154018
• Molecular Formular: C18H18N2O2
• Molecular Mass: 294.34772
• Monoisotopic Mass: 294.13682783
• SMILES: CC[C@@]1(C(=O)N(C(=O)N1)Cc1ccccc1)c1ccccc1
• Canonical SMILES: CC[C@]1(NC(=O)N(C1=O)Cc1ccccc1)c1ccccc1
• InChI: InChI=1S/C18H18N2O2/c1-2-18(15-11-7-4-8-12-15)16(21)20(17(22)19-18)13-14-9-5-3-6-10-14/h3-12H,2,13H2,1H3,(H,19,22)/t18-/m0/s1
• InChIKey: ZMZDHUHMXXALFX-SFHVURJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-3-benzyl-5-ethyl-5-phenylimidazolidine-2,4-dione
• IUPAC Traditional name: (5S)-3-benzyl-5-ethyl-5-phenylimidazolidine-2,4-dione
• Synonyms: (5S)-5-Ethyl-5-phenyl-3-(phenylmethyl)-2,4-imidazolidinedione; 5-ethyl-5-phenyl-3-(phenylmethyl)-2,4-imidazolidinedione; 5-ethyl-5-phenyl-3-(phenylmethyl)-hydantoin; 5-Ethyl-5-phenyl-3-(phenylmethyl)hydantoin; (+)-N-3-Benzylnirvanol; (S)-(+)-N-3-Benzylnirvanol; (+)-N-3-Benzyl Nirvanol

Database IDs

• CAS Number: 790676-40-3
• MDL Number: MFCD09840024
• PubChem SID: 162248157
• PubChem CID: 40633600

CALCULATED PROPERTIES

• Acid pKa: 11.207963
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.3896456
• LogD (pH = 7.4): 3.3895795
• Log P: 3.3896463
• Molar Refractivity: 84.1506 cm^3
• Polarizability: 32.652225 Å^3
• Polar Surface Area: 49.41 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >20 mg/mL; H2O: insoluble; Methanol
• Apperance: Off-White Solid; powder
• Melting Point: 147-150°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-36-50
• Safety Statements: 26-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319-H400
• GHS Precautionary statements: P273-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H18N2O2

DETAILS

Sigma Aldrich - B8686

Biochem/physiol Actions
(+)-N-3-Benzyl-nirvanol is a potent selective CYP2C19 inhibitor. CYP2C19 has a high frequency of drug resistance; highly polymorphic.

Toronto Research Chemicals - B285775

It is a potent and selective human CYP2C19 inhibitor.

REFERENCES

• Suzuki, H., et al.: Drug Metab. Dispos., 30, 235 (2002)
• Robert, L., et al.: Drug Metab. Dispos., 31, 343 (2002)