Stability of cefozopran hydrochloride in aqueous solutions / Przemysław Zalewski, Robert Skibiński, Magdalena Paczkowska, Piotr Garbacki, Alicja Talaczyńska, Judyta Cielecka-Piontek, Anna Jelińska
Abstract The influence of pH on the stability of cefozopran hydrochloride (CZH) was investigated in the pH range of 0.44–13.00. Six degradation products were identified with a hybrid ESI-Q-TOF mass spectrometer. The degradation of CZH as a result of hydrolysis was a pseudo-first-order reaction. As general acid–base hydrolysis of CZH was not occurred in the solutions of hydrochloric acid, sodium hydroxide, acetate, borate and phosphate buffers, k obs = k pH because specific acid–base catalysis was observed. Specific acid–base catalysis of CZH consisted of the following reactions: hydrolysis of CZH catalyzed by hydrogen ions ( k H+ ), hydrolysis of dications ( k 1H 2 O ), monocations ( k 2H 2 O ) and zwitter ions ( k 3H 2 O ) and hydrolysis of zwitter ions ( k 1OH− ) and monoanions ( k 2OH− ) of CZH catalyzed by hydroxide ions. The total rate of the reaction was equal to the sum of partial reactions: . CZH similarly like other fourth generation cephalosporin was most stable at slightly acidic and neutral pH and less stable in alkaline pH. The cleavage of the β-lactam ring resulting from a nucleophilic attack on the carbonyl carbon in the β-lactam moiety is the preferred degradation pathway of β-lactam antibiotics in aqueous solutions.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2016 |
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| Erschienen: |
2016 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:42 |
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| Enthalten in: |
Drug development and industrial pharmacy - 42(2016), 4, Seite 572- |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zalewski, Przemysław [VerfasserIn] |
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| Links: |
FID Access [lizenzpflichtig] |
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| Umfang: |
1 Online-Ressource (6 p) |
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| doi: |
10.3109/03639045.2015.1054834 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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KFL001083384 |
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| 520 | |a Abstract The influence of pH on the stability of cefozopran hydrochloride (CZH) was investigated in the pH range of 0.44–13.00. Six degradation products were identified with a hybrid ESI-Q-TOF mass spectrometer. The degradation of CZH as a result of hydrolysis was a pseudo-first-order reaction. As general acid–base hydrolysis of CZH was not occurred in the solutions of hydrochloric acid, sodium hydroxide, acetate, borate and phosphate buffers, k obs = k pH because specific acid–base catalysis was observed. Specific acid–base catalysis of CZH consisted of the following reactions: hydrolysis of CZH catalyzed by hydrogen ions ( k H+ ), hydrolysis of dications ( k 1H 2 O ), monocations ( k 2H 2 O ) and zwitter ions ( k 3H 2 O ) and hydrolysis of zwitter ions ( k 1OH− ) and monoanions ( k 2OH− ) of CZH catalyzed by hydroxide ions. The total rate of the reaction was equal to the sum of partial reactions: . CZH similarly like other fourth generation cephalosporin was most stable at slightly acidic and neutral pH and less stable in alkaline pH. The cleavage of the β-lactam ring resulting from a nucleophilic attack on the carbonyl carbon in the β-lactam moiety is the preferred degradation pathway of β-lactam antibiotics in aqueous solutions | ||
| 700 | 1 | |a Skibiński, Robert |e verfasserin |4 aut | |
| 700 | 1 | |a Paczkowska, Magdalena |e verfasserin |4 aut | |
| 700 | 1 | |a Garbacki, Piotr |e verfasserin |4 aut | |
| 700 | 1 | |a Talaczyńska, Alicja |e verfasserin |4 aut | |
| 700 | 1 | |a Cielecka-Piontek, Judyta |e verfasserin |4 aut | |
| 700 | 1 | |a Jelińska, Anna |e verfasserin |4 aut | |
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