Ezetimibe Azetidinone Ring opened impurity
Ezetimibe Azetidinone Ring opened impurity arises from the cleavage of the four-membered azetidinone core in ezetimibe, resulting in a linearized structure retaining the (4-fluorophenyl)amino moiety and the 2-oxoethyl side chain. The ring-opening introduces an exocyclic amino group conjugated to a ketone, disrupting the parent drug's lactam scaffold. This impurity features a fluorinated aromatic ring, an ether linkage, and a terminal carboxylic ester, maintaining key pharmacophoric elements while altering stereochemical constraints. It serves as an HPLC reference standard for quantifying process-related impurities in ezetimibe active pharmaceutical ingredient synthesis.
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Molecular Formula
C24H23F2NO4
Molecular Weight
427.4000
CAS Number
1391053-63-6
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PubChem CID
71316706 ↗
IUPAC Name
(2R,5S)-2-[(S)-(4-fluoroanilino)-(4-hydroxyphenyl)methyl]-5-(4-fluorophenyl)-5-hydroxypentanoic acid
Other CAS Numbers (also listed on PubChem)
1618657-29-6
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📝 Synonyms
1391053-63-6
Ezetimibe Azetidinone Ring-opened Impurity
1618657-29-6
(2R,5S)-2-[(S)-(4-fluoroanilino)-(4-hydroxyphenyl)methyl]-5-(4-fluorophenyl)-5-hydroxypentanoic acid
(2R,5S)-5-(4-Fluorophenyl)-2-((S)-((4-fluorophenyl)amino)(4-hydroxyphenyl)methyl)-5-hydroxypentanoic acid
Ezetimibe Impurity R
Ezetimibe Impurity 19
Ezetimibe Azetidinone Ring opened impurity
Ezetimibe Open-Ring Acid
4DK4W585N6
🔬 Chemical Identifiers
C1=CC(=CC=C1[C@H]([C@@H](CC[C@@H](C2=CC=C(C=C2)F)O)C(=O)O)NC3=CC=C(C=C3)F)O
InChI=1S/C24H23F2NO4/c25-17-5-1-15(2-6-17)22(29)14-13-21(24(30)31)23(16-3-11-20(28)12-4-16)27-19-9-7-18(26)8-10-19/h1-12,21-23,27-29H,13-14H2,(H,30,31)/t21-,22+,23-/m1/s1
XGNDFEVQHMNNOJ-XPWALMASSA-N
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