1-methyl-N-[(1S,5S)-9-methyl-9-azabicyclo[3.3.1]nonan-3-yl]-1H-indazole-3-carboxamide hydrochloride

• ChemBase ID: 179697
• Molecular Formular: C18H25ClN4O
• Molecular Mass: 348.8703
• Monoisotopic Mass: 348.17168912
• SMILES: c1(nn(c2c1cccc2)C)C(=O)NC1C[C@@H]2N([C@H](C1)CCC2)C.Cl
• Canonical SMILES: CN1[C@@H]2CCC[C@H]1CC(C2)NC(=O)c1nn(c2c1cccc2)C.Cl
• InChI: InChI=1S/C18H24N4O.ClH/c1-21-13-6-5-7-14(21)11-12(10-13)19-18(23)17-15-8-3-4-9-16(15)22(2)20-17;/h3-4,8-9,12-14H,5-7,10-11H2,1-2H3,(H,19,23);1H
• InChIKey: QYZRTBKYBJRGJB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-N-[(1S,5S)-9-methyl-9-azabicyclo[3.3.1]nonan-3-yl]-1H-indazole-3-carboxamide hydrochloride
• IUPAC Traditional name: 1-methyl-N-[(1S,5S)-9-methyl-9-azabicyclo[3.3.1]nonan-3-yl]-1H-indazole-3-carboxamide hydrochloride
• Synonyms: Kytril; Granisetron Hydrochloride

Database IDs

• CAS Number: 107007-99-8
• PubChem SID: 164235607
• PubChem CID: 49799997

CALCULATED PROPERTIES

• Acid pKa: 14.750399
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.3230767
• LogD (pH = 7.4): 0.2712485
• Log P: 1.8768568
• Molar Refractivity: 101.8257 cm^3
• Polarizability: 35.897053 Å^3
• Polar Surface Area: 50.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: 5HT3-receptor antagonist

Product Information

• Salt Data: HCl
• Application(s): Antiemetic

REFERENCES

• Eur. Pat., 1986, 200 444; CA, 106, 119892, (synth, pharmacol)
• Bermudez, J. et al., J. Med. Chem., 1990, 33, 1924, (synth)
• Goa, K.L. et al., Drugs, 1991, 42, 805, (rev)
• Kudoh, S. et al., J. Chromatogr., B: Biomed. Appl., 1994, 660, 205-210, (hplc)
• Adams, V.R. et al., Ann. Pharmacother., 1995, 29, 1240, (rev, pharmacol)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1193