| Photodegradation of fleroxacin injection: different products with different concentration levels. | |
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MedLine Citation:
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PMID: 21717376 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Photodegradation of fleroxacin is investigated in different injections and solutions. After UV irradiation, fleroxacin was degraded to afford two major products in large-volume injection (specification, 200 mg:100 ml), while degraded to afford another major product in small-volume injection (specification, 200 mg:2 ml). The photodegradation products were detected and isolated by reversed-phase HPLC. Based on the spectral data (FT-IR, MS(n), TOF-MS, (1)H/(13)C, DEPT, and 2D NMR), the structures of these products were: 8-fluoro-9-(4-methyl-piperazin-1-yl)-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid (impurity-I); 6-fluoro-1-(2-fluoro-ethyl)-7-(2-methylamino-ethylamino)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (impurity-II); and 6,8-difluoro-1-(2-fluoro-ethyl)-7-(2-methylamino-ethylamino)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (impurity-III), respectively. Different photodegradation pathways of fleroxacin were proposed, which led to the different stability characteristics of fleroxacin in the injections. The fluorine atom at C8 is more photolabile in dilute injection, so defluorination and cyclization reactions are prone to take place, whereas photo irradiation only cause ring-opening oxidation reaction of piperazine side chain in concentrated injection. |
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Authors:
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Jun Wang; Wei Li; Chen-Gui Li; Yu-Zhu Hu |
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Publication Detail:
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Type: Journal Article Date: 2011-06-30 |
Journal Detail:
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Title: AAPS PharmSciTech Volume: 12 ISSN: 1530-9932 ISO Abbreviation: AAPS PharmSciTech Publication Date: 2011 Sep |
Date Detail:
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Created Date: 2011-08-31 Completed Date: 2012-03-25 Revised Date: 2012-07-02 |
Medline Journal Info:
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Nlm Unique ID: 100960111 Medline TA: AAPS PharmSciTech Country: United States |
Other Details:
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Languages: eng Pagination: 872-8 Citation Subset: IM |
Affiliation:
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Key Laboratory of Drug Quality Control and Pharmacovigilance, Ministry of Education, Nanjing, China. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Anti-Infective Agents*
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chemistry,
radiation effects Chromatography, Reverse-Phase Cyclization / radiation effects Drug Stability Fleroxacin* / chemistry, radiation effects Heterocyclic Compounds, 3-Ring / chemistry Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Structure Oxidation-Reduction / radiation effects Photochemistry Photolysis / radiation effects* Quinolines / chemistry Solutions Spectroscopy, Fourier Transform Infrared Ultraviolet Rays |
| Chemical | |
Reg. No./Substance:
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0/6,8-difluoro-1-(2-fluoroethyl)-7-(2-methylaminoethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 0/6-fluoro-1-(2-fluoroethyl)-7-(2-methylaminoethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 0/8-fluoro-9-(4-methylpiperazin-1-yl)-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid; 0/Anti-Infective Agents; 0/Heterocyclic Compounds, 3-Ring; 0/Quinolines; 0/Solutions; 79660-72-3/Fleroxacin |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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