A kinetic study on the degradation of erythromycin A in aqueous solution

Kim, Yong‐Hak; Heinze, Thomas M.; Beger, Richard D.; Pothuluri, Jairaj V.; Cerniglia, Carl E.

doi:10.1016/j.ijpharm.2003.10.023

Cited by 63 publications

(44 citation statements)

References 22 publications

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“…Overall recovery, intermediate precision and measurement uncertainty were calculated using a combined computer program that consisted of SAS codes (SAS Software Release 9.1, SAS Institute Inc., USA) along with a Microsoft Excel (Microsoft Office 2002) workbook. [17] Results and discussion Chromatography Veterinary drugs or antibiotics included in this study were aminoglycosides (a total of 15), endectocides (7), fluoroquinolones (17), ionophores (6), b-Lactams (17) or penicillins (7), macrolides (7), NSAIDs (2), phenicols (2), sulfonamides (26), and tetracyclines (5). QqTOF data were acquired in TOFMS mode with a set of generic MS parameters that were applied to all analytes of interests.…”

Section: Experimental Design and Methods Validationmentioning

confidence: 99%

“…Erythromycin A-H 2 O appeared to be produced directly through an internal dehydration of erythromycin A-6,9-hemiketal which simultaneously established an equilibrium with erythromycin A enol ether ( Figure 5). [26] The determination of erythromycin A-H 2 O and its related degradation products (i.e. erythromycin A enol ether) in food could be of importance because the toxicity of the erythromycin A enol ether could be 5-fold higher than that of the parent compound [25,27] Therefore, the data from one of the incurred erythromycin A honey sample was examined based on the exact masses of 734.4691 (erythromycin A) and 716.4585 (erythromycin A-H 2 O or erythromycin A enol ether) and the extracted ion chromatograms were generated ( Figure 3).…”

Section: Confirmation and Unknown Identificationmentioning

confidence: 99%

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The challenges of developing a generic extraction procedure to analyze multi‐class veterinary drug residues in milk and honey using ultra‐high pressure liquid chromatography quadrupole time‐of‐flight mass spectrometry

Wang

Leung

2012

Drug Testing and Analysis

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This paper discusses the analytical challenges to develop a generic extraction procedure to analyze or screen multi-class veterinary drugs in milk and honey using ultra-high pressure liquid chromatography quadrupole time-of-flight mass spectrometry (UHPLC QqTOF MS). The veterinary drugs in this study included aminoglycosides, endectocides, fluoroquinolones, ionophores, b-lactams or penicillins, macrolides, NSAIDs, phenicols, sulfonamides and tetracyclines. Veterinary drugs were extracted using a QuEChERS (quick, easy, cheap, effective, rugged, and safe) method, which entailed the use of acetonitrile containing 1% acetic acid, sodium acetate, ethylenediaminetetra acetic acid disodium (EDTA) and magnesium sulfate, and no clean-up was performed. Chromatographic separation was achieved on a reversed-phase Acquity UPLC BEH C 18 , 100 Â 2.1 mm, 1.7 mm column with 0.1% formic acid and 10 mM ammonium formate in water, and acetonitrile as mobile phases. Due to poor chromatographic retention, aminoglycosides were first dropped from the list, and because of poor extractability, b-lactams and tetracyclines were also excluded from the method. The method was able to quantify 31 or screen up to 54 drugs (unbound) in honey, and to quantify 34 or screen up to 59 drugs in milk. UHPLC QqTOF data were acquired in TOF MS full-scan mode that allowed both quantification and confirmation of veterinary drugs and identification of their degradation products in samples. The method could achieve detection limits as low as 1 mg/kg with analytical range from 1 to 100 mg/kg. The developed method was intended to be used for screening of as many analytes as possible in one single analysis, or unequivocal confirmation of positive findings and degradation product identification based on accurate mass measurement and isotopic patterns.

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Section: Experimental Design and Methods Validationmentioning

confidence: 99%

Section: Confirmation and Unknown Identificationmentioning

confidence: 99%

The challenges of developing a generic extraction procedure to analyze multi‐class veterinary drug residues in milk and honey using ultra‐high pressure liquid chromatography quadrupole time‐of‐flight mass spectrometry

Wang

Leung

2012

Drug Testing and Analysis

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“…Disrupting this reaction sequence by modification of these involved functional groups resulted in stabilization of the parent antimicrobial structure with higher bioavailability and longer duration of antibiotic action. Later pharmacokinetic studies showed that a more complex equilibrium occurs during the cyclization reactions (42)(43)(44). The foremost second-generation derivatives are outlined below.…”

Section: Second-generation Derivatives Of Erythromycinmentioning

confidence: 99%

Macrolide Antibiotics

Kirst

2015

Kirk-Othmer Encyclopedia of Chemical Technology

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Macrolide antibiotics are one of the larger classes of fermentation‐derived natural products. In addition, many semisynthetic derivatives have been synthesized. They treat infections caused by most Gram‐positive bacteria, some susceptible Gram‐negative bacteria, and atypical bacteria such as Mycoplasma pneumoniae and Legionella pneumophila . They are orally bioavailable and accumulate in tissues and organs. They are regarded as one of the safest groups of antibiotics. Erythromycin is a 14‐membered ring macrolide and foremost member of the class. First‐generation derivatives focused on deficiencies such as compound instability in acidic environments, bitter taste, low water solubility, low oral bioavailability, and gastrointestinal and cardiac side effects. Many of these problems were at least partly solved by first‐generation derivatives such as esters and salts that made the active entities less prone to degradation. Second‐generation derivatives chemically changed substituents on the aglycone to stabilize it from intramolecular decomposition. This group includes clarithromycin and azithromycin that have become the most important macrolides to date. The problem of bacterial resistance to antibiotics was elegantly addressed by the ketolides. Telithromycin (Ketek®) was the first ketolide (third generation of erythromycin derivatives) to be approved and marketed, but postmarketing surveillance uncovered side effects and its use has been restricted. Macrolides are also important veterinary antibiotics and three new agents have been developed. Studies have continued to search for new agents using combinatorial biosynthesis, but the generation of large numbers of novel polyketides remains unfulfilled at this time.

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“…Erythromycin is easily converted to its metabolite, anhydro-erythromycin in acidic pH (Kim et al, 2004). In order to verify the efficiency of transformation of erythromycin to its anhydrous form, calibration solutions were prepared by spiking varying levels of stock solutions of erythromycin (or erythromycin -13 C-d3) into optima LC/MS water to which 20% optima LC/MS grade formic acid was added.…”

Section: Instrumentationmentioning

confidence: 99%

Assessment of the Occurrence and Potential Risks of Antibiotics and their Metabolites in South Florida Waters Using Liquid Chromatography Tandem Mass Spectrometry

Panditi¹

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This dissertation, written by Venkata Reddy Panditi, and entitled Assessment of the occurrence and potential risks of antibiotics and their metabolites in South Florida waters using liquid chromatography tandem mass spectrometry, having been approved in respect to style and intellectual content, is referred to you for judgment.We have read this dissertation and recommend that it be approved. _______________________________________Rudolf Jaffe Finally, all the antibiotics detected in reclaimed and surface waters were investigated to assess the potential risk to the aquatic organisms. The surface water antibiotic concentrations that represented the real time exposure conditions revealed that the macrolide antibiotics, erythromycin, clarithromycin and tylosin along with quinolone antibiotic, ciprofloxacin were suspected to induce high toxicity to aquatic biota.Preliminary results showing that, among the antibiotic groups tested, macrolides posed the highest ecological threat, and therefore, they may need to be further evaluated with, long-term exposure studies considering bioaccumulation factors and more number of species selected. Overall, the occurrence of antibiotics in aquatic environment is posing an ecological health concern.

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A kinetic study on the degradation of erythromycin A in aqueous solution

Cited by 63 publications

References 22 publications

The challenges of developing a generic extraction procedure to analyze multi‐class veterinary drug residues in milk and honey using ultra‐high pressure liquid chromatography quadrupole time‐of‐flight mass spectrometry

The challenges of developing a generic extraction procedure to analyze multi‐class veterinary drug residues in milk and honey using ultra‐high pressure liquid chromatography quadrupole time‐of‐flight mass spectrometry

Macrolide Antibiotics

Assessment of the Occurrence and Potential Risks of Antibiotics and their Metabolites in South Florida Waters Using Liquid Chromatography Tandem Mass Spectrometry

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