N-Nitroso Famotidine-II: Synthesis Attempts and Failure Report (NAP Test)

N‑Nitroso Famotidine‑II is a proposed nitrosamine impurity related to famotidine, an H2‑receptor antagonist. It represents an alternate/secondary nitrosated related substance (e.g., isomeric or positional variant) that could form under nitrosating conditions (such as nitrite/nitrous acid in acidic media) from nitrosatable nitrogens present in famotidine‑related structures.

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 Famotidine-II formation. Our findings revealed that N-Nitroso Famotidine-II 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 Famotidine-II Technical Information

• Molecular Weight: 367.4 g/mol
• Molecular Formula: C8H15N8O3S3
• IUPAC Name: (Z)-4-(((3-Amino-3-(sulfamoylimino)propyl)thio)methyl)-2-((diaminomethylene)amino)-3-nitrosothiazol-3-ium
• CAS Number: N/A
• Synonyms: N/A

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