9-hydroxy-2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide

• ChemBase ID: 167628
• Molecular Formular: C15H14N2O2
• Molecular Mass: 254.28386
• Monoisotopic Mass: 254.1055277
• SMILES: c12c(cccc1)N(c1c(cccc1)CC2O)C(=O)N
• Canonical SMILES: OC1Cc2ccccc2N(c2c1cccc2)C(=O)N
• InChI: InChI=1S/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)
• InChIKey: BMPDWHIDQYTSHX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-hydroxy-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide
• IUPAC Traditional name: 9-hydroxy-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide
• Synonyms: 10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide; 10-Hydroxy-10,11-dihydrocarbamezepine; BIA 2-005; GP 47779; Licarbazepine; 10,11-Dihydro-10-hydroxy Carbamazepine

Database IDs

• CAS Number: 29331-92-8
• PubChem SID: 162261761
• PubChem CID: 114709

CALCULATED PROPERTIES

• LogD (pH = 5.5): 1.731741
• LogD (pH = 7.4): 1.7317408
• Log P: 1.731741
• Molar Refractivity: 72.2869 cm^3
• Polarizability: 27.563173 Å^3
• Polar Surface Area: 66.56 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• Acid pKa: 14.100105
• H Acceptors: 2
• H Donor: 2

PROPERTIES

Physical Property

• Solubility: Chloroform; Dimethyl Sulfoxide; Ethanol
• Apperance: White to Off-White Solid
• Melting Point: 186-189°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D449135

A metabolite of Oxcarbazepine.

REFERENCES

• Burkhart, C., et al.: Clin. Exp. Allergy, 32, 1635 (2002)
• Pearce, R., et al.: Drug Metab. Dispos., 30, 1170 (2002)
• Naisbitt, D., et al.: Mol. Pharmacol., 63, 732 (2002)
• Farrell, J., et al.: Br. J. Clin. Pharmacol., 57, 690(2002)