Degradation of lansoprazole and omeprazole in the aquatic environment

DellaGreca, Marina; Iesce, M. R.; Previtera, Lucio; Rubino, Maria; Temussi, Fabio; Brigante, Marcello

doi:10.1016/j.chemosphere.2005.09.003

Cited by 68 publications

(46 citation statements)

References 16 publications

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“…In OMP-Na, the loss in mass was observed in two steps, the first one from 85°C 3 Journal of Spectroscopy to 110°C and the second one from 120°C to 160°C. Both steps are in the accordance with the release of two water molecules [5,6,8,[23][24][25]. In OMP-Mg, the loss in mass in two steps was also observed, from 85°C to 105°C and from 135°C to 170°C which is in accordance with the release of two water molecules [12].…”

Section: Resultssupporting

confidence: 64%

Spectroscopic Characterization of Omeprazole and Its Salts

Vrbanec

Šket

Merzel

et al. 2017

Journal of Spectroscopy

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During drug development, it is important to have a suitable crystalline form of the active pharmaceutical ingredient (API). Mostly, the basic options originate in the form of free base, acid, or salt. Substances that are stable only within a certain pH range are a challenge for the formulation. For the prazoles, which are known to be sensitive to degradation in an acid environment, the formulation is stabilized with alkaline additives or with the application of API formulated as basic salts. Therefore, preparation and characterization of basic salts are needed to monitor any possible salinization of free molecules. We synthesized salts of omeprazole from the group of alkali metals (Li, Na, and K) and alkaline earth metals (Mg, Ca). The purpose of the presented work is to demonstrate the applicability of vibrational spectroscopy to discriminate between the OMP and OMP-salt molecules. For this reason, the physicochemical properties of 5 salts were probed using infrared and Raman spectroscopy, NMR, TG, DSC, and theoretical calculation of vibrational frequencies. We found out that vibrational spectroscopy serves as an applicable spectroscopic tool which enables an accurate, quick, and nondestructive way to determine the characteristic of OMP and its salts.

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Section: Resultssupporting

confidence: 64%

Spectroscopic Characterization of Omeprazole and Its Salts

Vrbanec

Šket

Merzel

et al. 2017

Journal of Spectroscopy

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“…However, the bioavailability of LSP was not consistent with wide intersubject variation (1,4), which is ascribed to the variation in the genotype of CYP2C19, possible degradation by the gastric acid, and limited water solubility (4)(5)(6). Besides, LSP, as presented in formulations, suffer from chemical degradation due to its sensitivity to low pH and light (7). Solid dispersions of LSP/polyvinylpyrrolidone (PVP) system prepared by the fluid-bed coating techniques (8), as well as mixtures of LSP and surfactants adsorbed to porous particles (6), have been employed to improve the dissolution and oral bioavailability of LSP.…”

Section: Introductionmentioning

confidence: 99%

“…6). The sulfinyl is the most fragile part of LSP, as it is common for this group to be reduced to sulfide or be ruptured when LSP is under degradation (7). Inclusion of the sulfinyl group into CD cavity and the consequent protective effects on this group is the determinative factor for LSP stability.…”

Section: Stabilitymentioning

confidence: 99%

Enhanced Dissolution and Stability of Lansoprazole by Cyclodextrin Inclusion Complexation: Preparation, Characterization, and Molecular Modeling

Lü

Guo

et al. 2012

AAPS PharmSciTech

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Abstract. In this study, lansoprazole (LSP)/cyclodextrin (CD) inclusion complexes were prepared using a fluid bed coating technique, with β-cyclodextrin (β-CD) and 2-hydroxypropyl-β-cyclodextrin (HPCD) as the host molecules, respectively, to simultaneously improve the dissolution and stability of LSP. The dissolution rate and stability of LSP was dramatically enhanced by inclusion complexation regardless of CD type. LSP/ HPCD inclusion complex was more stable under illumination than LSP/β-CD inclusion complex. Differential scanning calorimetry and powder X-ray diffractometry proved the absence of crystallinity in both LSP/CD inclusion complexes. Fourier transform infrared spectroscopy together with molecular modeling indicated that the benzimidazole of LSP was included in the cavity of both CDs, while LSP was more deeply included in HPCD than β-CD. The enhanced photostability was due to the inclusion of the sulfinyl moiety into the HPCD cavity. CD inclusion complexation could improve the dissolution and stability of LSP.

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“…Thus, it seems clear that 279 omeprazole was unstable in aqueous solution and was transformed to 4-hydroxy omeprazole 280 sulfide. The degradation of omeprazole to the sulfide derivative in HPLC-grade water and kept 281 in dark has been previously reported in literature (DellaGreca et al 2006). In our study, the 282 transformation started to be more evident after 14 days of storage in the cooler (-4 ºC, 283 darkness).…”

mentioning

confidence: 99%

Investigation of pharmaceutical metabolites in environmental waters by LC-MS/MS

Gracia-Lor

Ibáñez

Zamora

et al. 2014

Environ Sci Pollut Res

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Pharmaceuticals, once ingested, are commonly metabolized in the body into more polar and soluble forms. These compounds might not be completely removed in the wastewater treatment plants and consequently being discharged into the aquatic ecosystem. In this work, a multi-class sensitive method for the analysis of 21 compounds, including 7 widely consumed pharmaceuticals and 14 relevant metabolites, has been developed based on the use of UHPLC-MS/MS in selected reaction monitoring (SRM) mode. The method was validated in six surface waters (SW) and six effluent wastewaters (EWW) at realistic concentration levels that can be found in waters. The optimized method was applied to the analysis of different types of water samples (rivers, lakes and effluent wastewater), detecting nearly all the parent compounds and metabolites investigated in this work. This fact illustrates that not only pharmaceuticals but also their metabolites are commonly present in these types of waters. Analytical research and monitoring programs should be directed not only towards parent pharmaceuticals but also towards relevant metabolites to have a realistic overview of the impact of pharmaceuticals in the aquatic environment.

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Degradation of lansoprazole and omeprazole in the aquatic environment

Cited by 68 publications

References 16 publications

Spectroscopic Characterization of Omeprazole and Its Salts

Spectroscopic Characterization of Omeprazole and Its Salts

Enhanced Dissolution and Stability of Lansoprazole by Cyclodextrin Inclusion Complexation: Preparation, Characterization, and Molecular Modeling

Investigation of pharmaceutical metabolites in environmental waters by LC-MS/MS

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