(2R,4S)-4-(4-acetylpiperazin-1-yl)-N-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-(4-fluoro-2-methylphenyl)-N-methylpiperidine-1-carboxamide; methanesulfonic acid

• ChemBase ID: 163847
• Molecular Formular: C31H39F7N4O5S
• Molecular Mass: 712.7189824
• Monoisotopic Mass: 712.25293891
• SMILES: C1[C@H](CCN([C@H]1c1ccc(cc1C)F)C(=O)N([C@@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C)C)N1CCN(CC1)C(=O)C.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.Fc1ccc(c(c1)C)[C@H]1C[C@H](CCN1C(=O)N([C@@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C)C)N1CCN(CC1)C(=O)C
• InChI: InChI=1S/C30H35F7N4O2.CH4O3S/c1-18-13-24(31)5-6-26(18)27-17-25(40-11-9-39(10-12-40)20(3)42)7-8-41(27)28(43)38(4)19(2)21-14-22(29(32,33)34)16-23(15-21)30(35,36)37;1-5(2,3)4/h5-6,13-16,19,25,27H,7-12,17H2,1-4H3;1H3,(H,2,3,4)/t19-,25+,27-;/m1./s1
• InChIKey: YRFKYVWDPCOSTE-REWBLLDVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S)-4-(4-acetylpiperazin-1-yl)-N-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-(4-fluoro-2-methylphenyl)-N-methylpiperidine-1-carboxamide; methanesulfonic acid
• IUPAC Traditional name: casopitant; methanesulfonic acid
• Synonyms: (2R,4S)-4-(4-Acetyl-1-piperazinyl)-N-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-(4-fluoro-2-methylphenyl)-N-methyl-1-piperidinecarboxamide Methanesulfonate; GW 679769B; Casopitant Mesylate

Database IDs

• CAS Number: 414910-30-8
• PubChem SID: 162257982
• PubChem CID: 11686295

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.1586938
• LogD (pH = 7.4): 4.709539
• Log P: 4.968799
• Molar Refractivity: 149.021 cm^3
• Polarizability: 54.8988 Å^3
• Polar Surface Area: 47.1 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C184800

It is a novel, orally active tachykinin NK1 receptor antagonist; efficacy of Casopitant mesilate in patients receiving emetogenic chemotherapy.

REFERENCES

• Hesketh, P., et al.: Eur. J. Cancer., 39, 1074 (2003)
• Kris, M., et al.: J. Clin. Oncol., 24, 2932 (2003)
• Minthorn, E., et al.: Drug Metab. Dispos., 36, 1846 (2003)