disodium (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl phosphate

• ChemBase ID: 169454
• Molecular Formular: C16H13N2Na2O6P
• Molecular Mass: 406.237521
• Monoisotopic Mass: 406.03066134
• SMILES: C1(=O)N(C(=O)NC1(c1ccccc1)c1ccccc1)COP(=O)([O-])[O-].[Na+].[Na+]
• Canonical SMILES: O=C1N(COP(=O)([O-])[O-])C(=O)NC1(c1ccccc1)c1ccccc1.[Na+].[Na+]
• InChI: InChI=1S/C16H15N2O6P.2Na/c19-14-16(12-7-3-1-4-8-12,13-9-5-2-6-10-13)17-15(20)18(14)11-24-25(21,22)23;;/h1-10H,11H2,(H,17,20)(H2,21,22,23);;/q;2*+1/p-2
• InChIKey: GQPXYJNXTAFDLT-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl phosphate
• IUPAC Traditional name: disodium (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl phosphate
• Synonyms: 5,5-Diphenyl-3-[(phosphonooxy)methyl]-2,4-imidazolidinedione Sodium Salt; ACC 9653; ACC 9653-010; CI 982; Cetebyx; Pro-Epanutin; Fosphenytoin Sodium

Database IDs

• CAS Number: 92134-98-0
• PubChem SID: 162263586
• PubChem CID: 56338

CALCULATED PROPERTIES

• Acid pKa: 1.4607412
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.74049556
• LogD (pH = 7.4): -1.6477319
• Log P: 1.6680293
• Molar Refractivity: 84.8103 cm^3
• Polarizability: 33.743156 Å^3
• Polar Surface Area: 121.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F728900

Phenytoin prodrug used in the treatment of epileptic seizures.

REFERENCES

• Hussey, E., et al.: Pharm. Res., 7, 1172 (1990)
• Ogutu, B., et al.: Brit. J. Clin. Pharmacol., 56, 464 (1990)
• Dhareshwar, S., et al.: J. Pharm. Sci., 99, 2711 (1990)