(9S)-9,10-dihydroxy-2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide

• ChemBase ID: 167599
• Molecular Formular: C15H14N2O3
• Molecular Mass: 270.28326
• Monoisotopic Mass: 270.10044232
• SMILES: [C@H]1(C(c2c(N(c3c1cccc3)C(=O)N)cccc2)O)O
• Canonical SMILES: OC1c2ccccc2N(c2c([C@@H]1O)cccc2)C(=O)N
• InChI: InChI=1S/C15H14N2O3/c16-15(20)17-11-7-3-1-5-9(11)13(18)14(19)10-6-2-4-8-12(10)17/h1-8,13-14,18-19H,(H2,16,20)/t13-,14?/m0/s1
• InChIKey: PRGQOPPDPVELEG-LSLKUGRBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9S)-9,10-dihydroxy-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide
• IUPAC Traditional name: (9S)-9,10-dihydroxy-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide
• Synonyms: (10R,11R)-rel-10,11-Dihydro-10,11-dihydroxy-5H-dibenz[b,f]azepine-5-carbox-amide; Dihydrocarbamazepine-10,11-trans-diol; Carbamazepine-10,11-dihydrodiol; Carbamazepine-10,11-dihydro-10,11-diol; 10,11-Dihydroxycarbamazepine; rac trans-10,11-Dihydro-10,11-dihydroxy Carbamazepine

Database IDs

• CAS Number: 35079-97-1
• PubChem SID: 162261732
• PubChem CID: 45039023

CALCULATED PROPERTIES

• Acid pKa: 12.835364
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.8127448
• LogD (pH = 7.4): 0.81274325
• Log P: 0.81274486
• Molar Refractivity: 73.4944 cm^3
• Polarizability: 28.264883 Å^3
• Polar Surface Area: 86.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 220-222°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D449040

A major metabolite of Carbamazepine (C175840).

REFERENCES

• Frigerio, A., et al.: J. Pharm. Sci., 61,1144 (1972)
• Lertratanangkoon, K., et al.: Drug Metab. Dispos., 10,1 (1972)