A Chromatographic and Spectroscopic Study of Photodegraded Metronidazole in Aqueous Solution

Godfrey, Russell; Edwards, R. W. H.

doi:10.1002/jps.2600800305

Cited by 10 publications

(6 citation statements)

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“…The analytic method developed was characterized by specificity, as excipients composing the tablets did not show absorbance at the analytical wavelengths of 277 nm and 320 nm. Of note: in this part of the study, we did not see that the degradation products of metronidazole that appear under the influence of light had any influence on the results of quantitative spectrophotometric analysis in UV [5].…”

Section: Evaluation Of Prepared Matrix Tabletsmentioning

confidence: 79%

Eudragit FS 30D as a potential polymer for use in the technology of preparing matrix tablets contain metronidazole – an experimental and mathematical modeling study

Letmanski

Kodym

Weber

et al. 2015

Current Issues in Pharmacy and Medical Sciences

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The aim of this study was to examine the usefulness of a pH-dependent copolymer - Eudragit FS - for employment in the technology of preparing modified release metronidazole matrix tablets. In addition, in our work, Eudragit RL and Eudragit RS were included in the composition of some formulations, as well as sodium lauryl sulfate and polysorbate 80. As part of the study of the dissolution test, the similarity coefficient (f2) for the obtained profiles was calculated, and mathematic models were used to estimate the kinetics and mechanism of active substance release. In our work, it was observed that the inclusion of polymer Eudragit FS alone in the tablet composition ensured a modified release of the active substance for 10 h. After this time period, the amount of metronidazole determined in the acceptor fluid was 71% - 81% of the declared dose. Modification of the composition by the addition of surfactants resulted in an increased release of the active substance of up to 98%. This effect was dependent on the type of surfactant and its quantitative ratio to the Eudragit FS. Similar release profiles were obtained for tablets containing Eudragit RS and sodium lauryl sulfate, as well as Eudragit RS and polysorbate 80. Depending on the composition of tablets, metronidazole release proceeded in accordance with either first or second-order kinetics. We calculated as well, that the differing masses of Eudragit FS in the studied formulations correlates with the order of release kinetics (p < 0.002). Such an effect was validated using the Weibull model, wherein, in all the studied formulations, the release rate was seen as a decreasing function of time. An analysis of data according to the Ritger-Peppas model and the Peppas-Sahlin model for some formulations, indicated that the mechanism of active substance release from matrix tablets is diffusion.

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Section: Evaluation Of Prepared Matrix Tabletsmentioning

confidence: 79%

Eudragit FS 30D as a potential polymer for use in the technology of preparing matrix tablets contain metronidazole – an experimental and mathematical modeling study

Letmanski

Kodym

Weber

et al. 2015

Current Issues in Pharmacy and Medical Sciences

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“…2 ), its corresponding UV spectrum (see Fig. 3 , with poor absorption at 315 nm) and related references 1 – 6 , it was identified as N -(2-hydroxy ethyl)-5-methyl-l,2,4- oxadiazole-3-carboxamide (CAS:110578-73-9) , whose production pathway was proposed by rearrangement of metronidazole as described in Fig. 1 1 – 3 .…”

Section: Resultsmentioning

confidence: 97%

“… In the structural characterization of the photolytic degradant in light stressed metronidazole samples (5000 lx, 30 days), based on reports 1 – 6 and our LC-PDA-MS results, it was proposed as N -(2-hydroxyethyl)-5-methyl-l,2,4-oxadiazole-3-carboxamide (CAS:110578-73-9). Its typical parent ions, characteristic product ions as well as extracted PDA spectrum were totally in agreement with those of references 1 – 6 . Further verification was performed by comparison with the corresponding reference substance, in terms of retention times and extracted PDA spectra under the same chromatographic condition (see “ LC-PDA experiments ” section), which were consistent with each other.…”

Section: Discussionmentioning

confidence: 95%

“…4 and supplementary materials [Stablity of metronidazole injection under UV irradiation (5000 lx)]. In the structural characterization of the photolytic degradant in light stressed metronidazole samples (5000 lx, 30 days), based on reports 1 – 6 and our LC-PDA-MS results, it was proposed as N -(2-hydroxyethyl)-5-methyl-l,2,4-oxadiazole-3-carboxamide (CAS:110578-73-9). Its typical parent ions, characteristic product ions as well as extracted PDA spectrum were totally in agreement with those of references 1 – 6 .…”

Section: Discussionmentioning

confidence: 99%

“…However, it is sensitive to light 1 – 11 and UV irradiation could lead to its rearrangement and the formation of N -(2-hydroxy ethyl)-5-methyl-l,2,4-oxadiazole-3-carboxamide (photolytic degradant, target compound in Fig. 1 ) via labile intermediates, especially in solution 1 – 6 .

Figure 1 Proposed photolytic rearrangement pathway of metronidazole to N -(2-hydroxyethyl)-5-methyl-l,2,4-oxadiazole-3-carboxamide 1 – 3 .…”

Section: Introductionmentioning

confidence: 99%

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Identification of the major photodegradant in metronidazole by LC-PDA-MS and its reveal in compendial methods

Chen

Yuan

et al. 2022

Sci Rep

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Metronidazole in aqueous solution is sensitive to light and UV irradiation, leading to the formation of N-(2-hydroxyethyl)-5-methyl-l,2,4-oxadiazole-3-carboxamide. This is revealed here by liquid chromatography with tandem photo diode array detection and mass spectrometry (LC-PDA-MS) and further verified by comparison with the corresponding reference substance and proton nuclear magnetic resonance (1H-NMR). However, in current compendial tests for related substances/organic impurities of metronidazole, the above photolytic degradant could not be detected. Thus, when photodegradation of metronidazole occurs, it could not be demonstrated. In our study, an improved LC method was developed and validated, which includes a detection at a wavelength of 230 nm and optimization of mobile phase composition thereby a better separation was obtained.

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Current state and prospects of NMR spectroscopy application in pharmaceutical analysis (a review)

Kartashov

1996

Pharm Chem J

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A Chromatographic and Spectroscopic Study of Photodegraded Metronidazole in Aqueous Solution

Cited by 10 publications

References 1 publication

Eudragit FS 30D as a potential polymer for use in the technology of preparing matrix tablets contain metronidazole – an experimental and mathematical modeling study

Eudragit FS 30D as a potential polymer for use in the technology of preparing matrix tablets contain metronidazole – an experimental and mathematical modeling study

Identification of the major photodegradant in metronidazole by LC-PDA-MS and its reveal in compendial methods

Current state and prospects of NMR spectroscopy application in pharmaceutical analysis (a review)

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