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

• ChemBase ID: 174741
• Molecular Formular: C15H14N2O2
• Molecular Mass: 254.28386
• Monoisotopic Mass: 254.1055277
• SMILES: C1[C@@H](c2c(N(c3c1cccc3)C(=O)N)cccc2)O
• Canonical SMILES: O[C@H]1Cc2ccccc2N(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)/t14-/m0/s1
• InChIKey: BMPDWHIDQYTSHX-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9S)-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: eslicarbazepine
• Synonyms: (10S)-10,11-Dihydro-10-hydroxy-5H-Dibenz[b,f]azepine-5-carboxamide; S-(+)-10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide; (S)-Licarbazepine; BIA 2-194; CGP 13751; Erelib; Eslicarbazepine; Pazzul; Stedesa; (S)-10-Monohydroxy-10,11-dihydro Carbamazepine(Eslicarbazepine)

Database IDs

• CAS Number: 104746-04-5
• PubChem SID: 164230651
• PubChem CID: 9881504

CALCULATED PROPERTIES

• Acid pKa: 14.100105
• H Acceptors: 2
• H Donor: 2
• 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

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol; Pyridine
• Apperance: White to Off-White Solid
• Melting Point: 188-190°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M546510

(S)-10-Monohydroxy-10,11-dihydro Carbamazepine is the metabolite of Eslicarbazepine acetate, (BIA 2-093), (E659000) a novel central nervous system drug.

REFERENCES

• Duncan, J., et al.: Br. J. Clin. Pharmacol., 53, 123 (2002)
• Almeida, L., et al.: J. Clin. Pharmacol., 45, 1062 (2002)
• Coppola, G., et al.: CNS Drugs, 18, 133 (2002)