N-[(2S)-piperidin-2-ylmethyl]-2,5-bis(2,2,2-trifluoroethoxy)benzamide

• ChemBase ID: 168996
• Molecular Formular: C17H20F6N2O3
• Molecular Mass: 414.3427192
• Monoisotopic Mass: 414.13781183
• SMILES: c1(ccc(c(c1)C(=O)NC[C@@H]1CCCCN1)OCC(F)(F)F)OCC(F)(F)F
• Canonical SMILES: O=C(c1cc(OCC(F)(F)F)ccc1OCC(F)(F)F)NC[C@@H]1CCCCN1
• InChI: InChI=1S/C17H20F6N2O3/c18-16(19,20)9-27-12-4-5-14(28-10-17(21,22)23)13(7-12)15(26)25-8-11-3-1-2-6-24-11/h4-5,7,11,24H,1-3,6,8-10H2,(H,25,26)/t11-/m0/s1
• InChIKey: DJBNUMBKLMJRSA-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S)-piperidin-2-ylmethyl]-2,5-bis(2,2,2-trifluoroethoxy)benzamide
• IUPAC Traditional name: N-[(2S)-piperidin-2-ylmethyl]-2,5-bis(2,2,2-trifluoroethoxy)benzamide
• Synonyms: N-[(2S)-2-Piperidinylmethyl]-2,5-bis(2,2,2-trifluoroethoxy)benzamide; (S)-Flecainide; (+)-Flecainide; S-(+)-Flecainide

Database IDs

• CAS Number: 99495-92-8
• PubChem SID: 162263128
• PubChem CID: 6604414

CALCULATED PROPERTIES

• Acid pKa: 13.681352
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.944676E-4
• LogD (pH = 7.4): 1.0079992
• Log P: 3.1881418
• Molar Refractivity: 88.3963 cm^3
• Polarizability: 32.706814 Å^3
• Polar Surface Area: 59.59 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F389995

S-Enantiomer of Flecainide. Antiarrhythmic (class IC).

REFERENCES

• Hodess, A.B., et al.: J. Cardiovasc. Pharmacol., 1, 427 (1979)
• Somani, P., et al.: Clin. Pharmacol. Ther., 27, 464 (1979)
• Alessi-Severini, S., et al.: Anal. Profiles Drug Subs. Excip., 21, 169 (1992)