Characterization of impurities in spiramycin by liquid chromatography/ion trap mass spectrometry

Abstract

A reversed-phase liquid chromatography/tandem mass spectrometry method is described for the investigation of spiramycin and related substances. The method uses an XTerra C18 column (250 x 4.6 mm i.d.), 5 microm, and a mobile phase consisting of acetonitrile, methanol, water and ammonium acetate solution, pH 6.5. Mass spectral data were acquired on an LCQ ion trap mass spectrometer equipped with atmospheric pressure chemical ionization (APCI) operated in the positive ion mode. Using this method, the fragmentation behavior of spiramycin and its related substances was studied and the unknown impurities occurring in commercial samples were investigated. In total 17 compounds were identified, among which three reported as specified impurities in the European Pharmacopoeia. The other impurities showed mainly a modification in the forosamine sugar or in the substituent at C-3 and C-6 positions. In one impurity, the mycarose sugar is absent.

Efficient and simple HPLC method for spiramycin determination in urine samples and in pharmaceutical tablets

“…A considerable number of reports make use of LC coupled to various detection methods like UV , electrochemical (ECD) and MS . From the following, LC–MS/MS techniques are the most sensitive, powerful and reliable for these analyses . The microbiological assays can be used for screening procedures, however these often do not discriminate antibiotics well enough.…”

“…It fills in all the requirements in terms of sensitivity, precision and specificity bound with operating simplicity and rapid detection of SPI and other macrolides in biological and pharmaceutical samples. A considerable number of reports make use of LC coupled to various detection methods like UV [7][8][9][10], electrochemical (ECD) [11] and MS [12][13][14][15]. From the following, LC-MS/MS techniques are the most sensitive, powerful and F I G U R E 1 Chemical structure of spiramycin reliable for these analyses [14,15].…”

Impurity analysis of gentamicin bulk samples by improved liquid chromatography-ion trap mass spectrometry

“…Pre-column derivatization, RI and ELSD detection have shortcomings for analysis of gentamicin like sensitivi- ty and efficiency [40]. Mass spectrometry is highly selective and specific in the determination and confirmation of aminoglycoside [41], LC-MS method has been successfully used on analysis of antibiotics [41][42][43][44][45]. The purity of pharmaceutical products and identification of impurities is considered as essential to ensure drug safety and quality.…”

Post-PKS Tailoring Steps of the Spiramycin Macrolactone Ring in Streptomyces ambofaciens

“…These compounds were identified as C-19-methyl-spiramycins I, II, and III (compounds 10, 11, and 12 [ Fig. 1]) by their masses and fragmentation patterns (compared with the fragmentation patterns of spiramycins I, II, and III [19,20]) (see also Fig. S2 in the supplemental material).…”