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Photodegradation assessment of ciprofloxacin, moxifloxacin, norfloxacin and ofloxacin in the presence of excipients from tablets by UPLC-MS/MS and DSC.

Hubicka U, Zmudzki P, Talik P, Zuromska-Witek B, Krzek J - Chem Cent J (2013)

Bottom Line: Fluoroquinolones are compounds susceptible to photodegradation process, which may lead to reduction of their antibacterial activity and to induce phototoxicity as a side effect.Photodegradation process of analyzed drugs was confirmed by differential scanning calorimetry.In addition, the identification of degradation products was carried out by mass spectrometry.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Inorganic and Analytical Chemistry, Jagiellonian University Medical College, Faculty of Pharmacy, 9 Medyczna Street, 30-688 Kraków, Poland.

ABSTRACT

Background: Ciprofloxacin (CIP), moxifloxacin (MOX), norfloxacin (NOR) and ofloxacin (OFL), are the antibacterial synthetic drugs, belonging to the fluoroquinolones group. Fluoroquinolones are compounds susceptible to photodegradation process, which may lead to reduction of their antibacterial activity and to induce phototoxicity as a side effect. This paper describes a simple, sensitive UPLC-MS/MS method for the determination of CIP, MOX, NOR and OFL in the presence of photodegradation products.

Results: Chromatographic separations were carried out using the Acquity UPLC BEH C18 column; (2.1 × 100 mm, 1.7 μm particle size). The column was maintained at 40°C, and the following gradient was used: 0 min, 95% of eluent A and 5% of eluent B; 10 min, 0% of eluent A and 100% of eluent B, at a flow rate of 0.3 mL min(-1). Eluent A: 0.1% (v/v) formic acid in water; eluent B: 0.1% (v/v) formic acid in acetonitrile. The method was validated and all the validation parameters were in the ranges acceptable by the guidelines for analytical method validation. The photodegradation of examined fluoroquinolones in solid phase in the presence of excipients followed kinetic of the first order reaction and depended upon the type of analyzed drugs and coexisting substances. Photodegradation process of analyzed drugs was confirmed by differential scanning calorimetry. In addition, the identification of degradation products was carried out by mass spectrometry.

Conclusion: The developed UPLC-MS/MS method enables the determination of CIP, MOX, NOR and OFL in the presence of photodegradation products and identification of photodegradation products.

No MeSH data available.


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The DSC curves of the examined fluoroquinolones; dotted line: before exposure and continuous line: after exposure to UVA; A – CIP, B – MOX, C – NOR, D – OFL.
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Figure 3: The DSC curves of the examined fluoroquinolones; dotted line: before exposure and continuous line: after exposure to UVA; A – CIP, B – MOX, C – NOR, D – OFL.

Mentions: The sample of powdered CIP tablets exposed to UVA shows a number of similarities and differences in comparison to the sample not exposed (Figure 3A). In the temperature range of 104-174°C a broad endotherm, associated with the dehydration process, is observed [24] while there is no endothermic transition at Tmax = 238.0°C [25]. Moreover, there are two small endothermic peaks at Tmax = 179.5°C and Tmax = 205.5°C coming from the melting processes of the newly created chemical compounds. Endothermic peak of simultaneous melting and decomposition process has a smaller value of enthalpy ΔH = 12.8 mJ mg-1 and has been moved toward lower temperatures of Tmax = 299.5°C and Tmax = 302.1°C.


Photodegradation assessment of ciprofloxacin, moxifloxacin, norfloxacin and ofloxacin in the presence of excipients from tablets by UPLC-MS/MS and DSC.

Hubicka U, Zmudzki P, Talik P, Zuromska-Witek B, Krzek J - Chem Cent J (2013)

The DSC curves of the examined fluoroquinolones; dotted line: before exposure and continuous line: after exposure to UVA; A – CIP, B – MOX, C – NOR, D – OFL.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3750423&req=5

Figure 3: The DSC curves of the examined fluoroquinolones; dotted line: before exposure and continuous line: after exposure to UVA; A – CIP, B – MOX, C – NOR, D – OFL.
Mentions: The sample of powdered CIP tablets exposed to UVA shows a number of similarities and differences in comparison to the sample not exposed (Figure 3A). In the temperature range of 104-174°C a broad endotherm, associated with the dehydration process, is observed [24] while there is no endothermic transition at Tmax = 238.0°C [25]. Moreover, there are two small endothermic peaks at Tmax = 179.5°C and Tmax = 205.5°C coming from the melting processes of the newly created chemical compounds. Endothermic peak of simultaneous melting and decomposition process has a smaller value of enthalpy ΔH = 12.8 mJ mg-1 and has been moved toward lower temperatures of Tmax = 299.5°C and Tmax = 302.1°C.

Bottom Line: Fluoroquinolones are compounds susceptible to photodegradation process, which may lead to reduction of their antibacterial activity and to induce phototoxicity as a side effect.Photodegradation process of analyzed drugs was confirmed by differential scanning calorimetry.In addition, the identification of degradation products was carried out by mass spectrometry.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Inorganic and Analytical Chemistry, Jagiellonian University Medical College, Faculty of Pharmacy, 9 Medyczna Street, 30-688 Kraków, Poland.

ABSTRACT

Background: Ciprofloxacin (CIP), moxifloxacin (MOX), norfloxacin (NOR) and ofloxacin (OFL), are the antibacterial synthetic drugs, belonging to the fluoroquinolones group. Fluoroquinolones are compounds susceptible to photodegradation process, which may lead to reduction of their antibacterial activity and to induce phototoxicity as a side effect. This paper describes a simple, sensitive UPLC-MS/MS method for the determination of CIP, MOX, NOR and OFL in the presence of photodegradation products.

Results: Chromatographic separations were carried out using the Acquity UPLC BEH C18 column; (2.1 × 100 mm, 1.7 μm particle size). The column was maintained at 40°C, and the following gradient was used: 0 min, 95% of eluent A and 5% of eluent B; 10 min, 0% of eluent A and 100% of eluent B, at a flow rate of 0.3 mL min(-1). Eluent A: 0.1% (v/v) formic acid in water; eluent B: 0.1% (v/v) formic acid in acetonitrile. The method was validated and all the validation parameters were in the ranges acceptable by the guidelines for analytical method validation. The photodegradation of examined fluoroquinolones in solid phase in the presence of excipients followed kinetic of the first order reaction and depended upon the type of analyzed drugs and coexisting substances. Photodegradation process of analyzed drugs was confirmed by differential scanning calorimetry. In addition, the identification of degradation products was carried out by mass spectrometry.

Conclusion: The developed UPLC-MS/MS method enables the determination of CIP, MOX, NOR and OFL in the presence of photodegradation products and identification of photodegradation products.

No MeSH data available.


Related in: MedlinePlus