Ampicillin, discovered in 1958, was the first broad spectrum semisynthetic penicillin introduced into the market. Despite its wide use not all the impurities have been identified to date. Herein, the last unknown impurity present in commercially available medicines was isolated and identified. This impurity that accounts up to 0.8 in area % by HPLC (EP 10.0) in the Reference Listed Drugs (RLD) was characterized and identified to be the 16-keto penicillin G. The structure was confirmed by comparison with a chemically synthesized sample. The determination of the Relative Response Factor (RRF) of the impurity respect to the parent drug allowed to recalculate the real amount that is consistently below the reporting threshold.

Ampicillin sodium: Isolation, identification and synthesis of the last unknown impurity after 60 years of clinical use

Alessandra Tolomelli;Lucia Ferrazzano;Giulia Martelli;Alexia Mattellone;Walter Cabri
2020

Abstract

Ampicillin, discovered in 1958, was the first broad spectrum semisynthetic penicillin introduced into the market. Despite its wide use not all the impurities have been identified to date. Herein, the last unknown impurity present in commercially available medicines was isolated and identified. This impurity that accounts up to 0.8 in area % by HPLC (EP 10.0) in the Reference Listed Drugs (RLD) was characterized and identified to be the 16-keto penicillin G. The structure was confirmed by comparison with a chemically synthesized sample. The determination of the Relative Response Factor (RRF) of the impurity respect to the parent drug allowed to recalculate the real amount that is consistently below the reporting threshold.
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
Alessandra Tolomelli; Antonio Ricci; Angelo Viola; Michele Bassan; Luca Ferrari; Lucia Ferrazzano; Giulia Martelli; Alexia Mattellone; Walter Cabri
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/772404
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