Document Detail


Photodegradation of fleroxacin injection: different products with different concentration levels.
MedLine Citation:
PMID:  21717376     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Jun Wang; Wei Li; Chen-Gui Li; Yu-Zhu Hu
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Publication Detail:
Type:  Journal Article     Date:  2011-06-30
Journal Detail:
Title:  AAPS PharmSciTech     Volume:  12     ISSN:  1530-9932     ISO Abbreviation:  AAPS PharmSciTech     Publication Date:  2011 Sep 
Date Detail:
Created Date:  2011-08-31     Completed Date:  2012-03-25     Revised Date:  2013-06-28    
Medline Journal Info:
Nlm Unique ID:  100960111     Medline TA:  AAPS PharmSciTech     Country:  United States    
Other Details:
Languages:  eng     Pagination:  872-8     Citation Subset:  IM    
Affiliation:
Key Laboratory of Drug Quality Control and Pharmacovigilance, Ministry of Education, Nanjing, China.
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MeSH Terms
Descriptor/Qualifier:
Anti-Infective Agents* / 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:
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
Comments/Corrections

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