(5R)-3-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-3-azatricyclo[7.3.1.05,13]trideca-1(12),9(13),10-trien-2-one hydrochloride

• ChemBase ID: 176209
• Molecular Formular: C19H25ClN2O
• Molecular Mass: 332.8676
• Monoisotopic Mass: 332.16554111
• SMILES: c12c3cccc1C(=O)N(C[C@@H]2CCC3)[C@@H]1C2CCN(C1)CC2.Cl
• Canonical SMILES: O=C1N(C[C@H]2c3c1cccc3CCC2)[C@H]1CN2CCC1CC2.Cl
• InChI: InChI=1S/C19H24N2O.ClH/c22-19-16-6-2-4-14-3-1-5-15(18(14)16)11-21(19)17-12-20-9-7-13(17)8-10-20;/h2,4,6,13,15,17H,1,3,5,7-12H2;1H/t15-,17-;/m0./s1
• InChIKey: OLDRWYVIKMSFFB-NBLXOJGSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-3-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(12),9(13),10-trien-2-one hydrochloride
• IUPAC Traditional name: (5R)-3-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(12),9(13),10-trien-2-one hydrochloride
• Synonyms: (3aR)-2-(3R)-1-Azabicyclo[2.2.2]oct-3-yl-2,3,3a,4,5,6-hexahydro-1H-benz[de]isoquinolin-1-one Hydrochloride; RS 25259-198; (R,R)-Palonosetron Hydrochloride

Database IDs

• CAS Number: 135729-75-8
• PubChem SID: 164232119
• PubChem CID: 18651160

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.109810375
• LogD (pH = 7.4): 1.8701022
• Log P: 2.5460126
• Molar Refractivity: 88.5213 cm^3
• Polarizability: 33.791428 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P165805

Serotonin 5-HT3 receptor antagonist used in the prevention and treatment of chemotherapy-induced nausea and vomiting (CINV). Antiemetic.

REFERENCES

• Clark, R.D., et al.: J. Med. Chem., 36, 2645 (1993)
• Wong, E.H.F., et al.: Br. J. Pharmacol., 114, 851 (1993)
• Grunberg, S.M., et al.: Expert. Opin. Pharmacother., 4, 2297 (1993)
• Eisenberg, P., et al.: Ann. Oncol., 15, 330 (1993)
• Siddiqui, M.A.A., et al