(4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-hydroxy(1,2,3,4,5,6-13C6)phenyl]azetidin-2-one

• ChemBase ID: 168842
• Molecular Formular: C24H21F2NO3
• Molecular Mass: 415.38117543
• Monoisotopic Mass: 415.16907901
• SMILES: c1cc(ccc1[C@H](CCC1C(=O)N([C@@H]1[13c]1[13cH][13cH][13c]([13cH][13cH]1)O)c1ccc(cc1)F)O)F
• Canonical SMILES: O[13c]1[13cH][13cH][13c]([13cH][13cH]1)[C@@H]1C(CC[C@@H](c2ccc(cc2)F)O)C(=O)N1c1ccc(cc1)F
• InChI: InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21?,22-,23+/m0/s1/i3+1,4+1,11+1,12+1,16+1,20+1
• InChIKey: OLNTVTPDXPETLC-ZCFLNKIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-hydroxy(1,2,3,4,5,6-^1^3C₆)phenyl]azetidin-2-one
• IUPAC Traditional name: (4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-hydroxy(1,2,3,4,5,6-^1^3C₆)phenyl]azetidin-2-one
• Synonyms: (3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl-13C6)-2-azetidinone; Sch-58235-13C6; Ezetimibe-13C6

Database IDs

• CAS Number: 438624-68-1
• PubChem SID: 162262974
• PubChem CID: 71316703

CALCULATED PROPERTIES

• Acid pKa: 9.484299
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.559083
• LogD (pH = 7.4): 4.555587
• Log P: 4.559128
• Molar Refractivity: 108.8617 cm^3
• Polarizability: 41.585533 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E975007

Labelled Ezetimibe (E975000), an antihyperlipoproteinemic. A Cholesterol absorption inhibitor.

REFERENCES

• van Heek, M., at al.: J. Pharmacol. Exp. Ther., 283, 157 (1997)
• van Heek, M., at al.: Brit. J. Pharmacol., 129, 1748 (2000)