N-Nitroso Ezetimibe Azetidinone Ring Opened Impurity; Synthesis Attempts and Failure Report (NAP Test)

N‑Nitroso Ezetimibe Azetidinone Ring Opened Impurity is a proposed nitrosamine‑related impurity derived from ezetimibe, a cholesterol absorption inhibitor. It is associated with opening of the azetidinone (β‑lactam) ring, and under strongly nitrosating conditions the lactam/amide nitrogen in this related substance may undergo N‑nitrosation to form the corresponding N‑nitroso impurity.

EMA Guidance on Nitrosamines

According to EMA guidelines, if repeated synthesis attempts fail to detect the formation of nitrosamine impurities, it is likely that the impurity either does not exist or poses an extremely low risk.

Nitrosation

We conducted multiple nitrosation assays under rigorous forced conditions (NAP tests), to evaluate the risk of N-Nitroso Ezetimibe Azetidinone Ring Opened Impurity formation. Our findings revealed that N-Nitroso Ezetimibe Azetidinone Ring Opened Impurity does not readily undergo nitrosation under the expected conditions, significantly reducing concerns about its potential formation.

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Our synthesis failure report provides a detailed account of the findings from our synthesis attempts and rigorous testing, demonstrating the non-formation of the nitroso impurity. It offers a comprehensive overview of the evaluated conditions and the resulting data.

N-Nitroso Ezetimibe Azetidinone Ring Opened Impurity Technical Information

• Molecular Weight: 456.44 g/mol
• Molecular Formula: C24H22F2N2O5
• IUPAC Name: (5S)-5-(4-fluorophenyl)-2-((S)-((4-fluorophenyl)(nitroso)amino)(4-hydroxyphenyl)methyl)-5-hydroxypentanoic acid
• CAS Number: N/A
• Synonyms: N/A

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