N-{9-azabicyclo[3.3.1]nonan-3-yl}-1-methyl-1H-indazole-3-carboxamide

• ChemBase ID: 166505
• Molecular Formular: C17H22N4O
• Molecular Mass: 298.38278
• Monoisotopic Mass: 298.17936134
• SMILES: C1CCC2CC(CC1N2)NC(=O)c1c2c(n(n1)C)cccc2
• Canonical SMILES: O=C(c1nn(c2c1cccc2)C)NC1CC2CCCC(C1)N2
• InChI: InChI=1S/C17H22N4O/c1-21-15-8-3-2-7-14(15)16(20-21)17(22)19-13-9-11-5-4-6-12(10-13)18-11/h2-3,7-8,11-13,18H,4-6,9-10H2,1H3,(H,19,22)
• InChIKey: VIGVTDRZHFWDBM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{9-azabicyclo[3.3.1]nonan-3-yl}-1-methyl-1H-indazole-3-carboxamide
• IUPAC Traditional name: N-{9-azabicyclo[3.3.1]nonan-3-yl}-1-methylindazole-3-carboxamide
• Synonyms: N-(3-endo)-9-Azabicyclo[3.3.1]non-3-yl-1-methyl-1H-indazole-3-carboxamide; Granisetron Impurity C; 9'-Desmethyl Granisetron (Granisetron Impurity C)

Database IDs

• CAS Number: 160177-67-3
• PubChem SID: 162260638
• PubChem CID: 45038885

CALCULATED PROPERTIES

• Acid pKa: 14.75041
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.7286521
• LogD (pH = 7.4): -1.0805823
• Log P: 1.4938089
• Molar Refractivity: 96.531 cm^3
• Polarizability: 34.05281 Å^3
• Polar Surface Area: 58.95 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 155-158°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D292040

An impurity in the synthesis of Granisetron Hydrochloride.

REFERENCES

• Nishikawa, M., et al.: Drug Metab. Pharmacokin., 19, 280 (2004)
• Firkusny, L., et al.: Biochem. Pharmacol., 49, 1777 (2004)
• Sanwald, P., et al.: Drug Metab. Dispos., 24, 602 (2004)
• Vanderstreene, et al.: J. Labelled Comp. Radiopharm., XLI, 3, 71 (2004)