(5S)-3-[(3S)-(3-2H)-1-azabicyclo[2.2.2]octan-3-yl](4,4-2H2)-3-azatricyclo[7.3.1.05,13]trideca-1(12),9(13),10-trien-2-one hydrochloride

• ChemBase ID: 176208
• 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?;/m1./s1
• InChIKey: OLDRWYVIKMSFFB-GKDMBGIGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-3-[(3S)-(3-^2H)-1-azabicyclo[2.2.2]octan-3-yl](4,4-^2H₂)-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(12),9(13),10-trien-2-one hydrochloride
• IUPAC Traditional name: (5S)-3-[(3S)-(3-^2H)-1-azabicyclo[2.2.2]octan-3-yl](4,4-^2H₂)-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(12),9(13),10-trien-2-one hydrochloride
• Synonyms: (3aS)-2-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-2,3,3a,4,5,6-hexahydro-1H-benz[de]isoquinolin-1-one-d3 Hydrochloride; Aloxi-d3; Onicit-d3; RS-25259-197-d3; (S,S)-Palonosetron-d3 Hydrochloride

Database IDs

• PubChem SID: 164232118
• PubChem CID: 71751455

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: 33.791763 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: >297-299°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - P165802

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