Degradation Products of Chloramphenicol

Shih, I.K.

doi:10.1002/jps.2600600527

Cited by 14 publications

(9 citation statements)

References 2 publications

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“…products of degradation such as for example the 1-(p-nitrophenyl)-2-amino-propanediol molecules. The occurrence of partial degradation was confirmed by direct observation of the sample at the end of the experiment: while pure CAP is white, the outcome of melting the asstored CAP sample was a viscous yellow-brownish liquid, with a color similar to that previously reported for sunlight degraded CAP 29. To analyze the outcome of degradation, we have recorded the FTIR spectrum of the degraded sample (after annealing for 3600 s at 433 K) and compared it to the spectrum of the pure (vacuum-dried) sample.…”

supporting

confidence: 76%

“…In the former case, the products of degradation are 1-(p-nitrophenyl)-2-amino-propanediol and dichloroacetic acid, while in the latter case they are a Cl-substituted alcohol CAP derivative and (at least partially) dissociated hidrochloric acid, 30 but other secondary pathways that lead to degradation may exist. 29 Furthermore it was reported that, while water-free preparations show no sign of degradation (pure CAP does not degrade upon melting 54 ), detectable amounts of these degradation products are present in aqueous solutions as well as in preparations of CAP with relatively low amounts of water (e.g., condensed from humid air). Recent studies 55,56 report that the half-life of CAP in water at 333 K is of the order of 20 days, and that in boiling water CAP exhibits 12% degradation in 1 hour.…”

Section: Resultsmentioning

confidence: 99%

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Tuning the Kinetic Stability of the Amorphous Phase of the Chloramphenicol Antibiotic

et al. 2018

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We employ broadband dielectric spectroscopy to study the relaxation dynamics and crystallization kinetics of a broad-spectrum antibiotic, chloramphenicol, in its supercooled liquid form. Two dynamic processes are observed: the structural α relaxation, which becomes kinetically frozen at T g = 302 ± 1 K, and an intramolecular secondary relaxation. Under isothermal conditions, the supercooled drug displays interconversion between different isomers, followed by recrystallization. Recrystallization follows the Avrami law with Avrami exponent n = 1.3 ± 0.1, consistent with a one dimensional growth of crystalline platelets, as observed by electron microscopy. Exposure to humid atmosphere and subsequent heating to high temperature is found to degrade the compound. The partially degraded sample displays a much lower tendency to crystallize, likely because the presence of the degradation products results in spatial frustration. This sample exhibits enhanced conductivity and an additional relaxation, intermediate to the ones observed in the pure sample, which likely corresponds to the noncooperative dynamics of the main degradation product. We find that dispersing the antibiotic in polylactic acid results in an amorphous sample which does not crystallize at room temperature for relatively long times.

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supporting

confidence: 76%

Section: Resultsmentioning

confidence: 99%

Tuning the Kinetic Stability of the Amorphous Phase of the Chloramphenicol Antibiotic

et al. 2018

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“…MS/MS spectra of the m/z 213 in the metabolite spectra yielded fragment ions m/z 195, 165 corresponding to the loss of H 2 O, C 2 HOCl 2 + CH 2 OH + H 2 O from the metabolite (data not shown). These data confirm 1-p-nitrophenyl-2-amino-1,3-propanediol as the observed species (Brock, 1961;Shin, 1971;Zeegers & Gibella, 1997).…”

Section: Lc-ms/ms Analysis Of Metabolitessupporting

confidence: 81%

“…11a). These data confirm 1-p-nitrophenyl-2-amino-1,3-propanediol as the observed species (Brock, 1961;Shin, 1971;Zeegers & Gibella, 1997). 11b, implying that two chlorine atoms are reduced from the parent CAP.…”

Section: Lc-ms/ms Analysis Of Metabolitessupporting

confidence: 70%

Isolation, identification and characterization of human intestinal bacteria with the ability to utilize chloramphenicol as the sole source of carbon and energy

Zhao

Tian

Wang

et al. 2012

FEMS Microbiol Ecol

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Five aerobic intestinal bacterial strains that utilized chloramphenicol (CAP) as sole carbon and energy source were isolated from fecal samples collected from healthy volunteers. Based on 16S rRNA gene sequence analysis, four of the five strains were identified as Klebsiella pneumoniae and one as Escherichia fergusonii. The degradation rate of strain I‐10‐CHL (E. fergusonii) varied with the initial concentration of CAP. The pH value also had an effect on the degradation rate of CAP and bacterial growth. A pH of 6.5 was optimal for CAP degradation and growth of strain I‐10‐CHL (E. fergusonii). In mixed substrate batch cultivations, where CAP was one of the components, glucose, acetamide and CAP were utilized simultaneously. The presence of glucose and acetamide increased the growth and substrate degradation rates of CAP. During incubation with E. fergusonii cells, reduction intermediates (1‐p‐nitrophenyl‐2‐amino‐1,3‐propanediol) were observed. The strains capable of utilizing CAP were CAP‐susceptible, which indicates that the mechanism of CAP assimilation by the strains is independent on that of CAP resistance. The role of this CAP reduction pathway in the physiology of K. pneumoniae and E. fergusonii is unknown.

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“…The chemistry of the photo-degradation products of chloramphenicol aqueous solution at room temperature (21-30ºC) and in the presence of sunlight, suggest that under the influence of light and water the drug undergoes oxidation, reduction and condensation reactions. The photochemical degradation of chloramphenicol in various solvents was investigated and the following photolysis products isolated: hydrochloric acid, 4-nitrobenzaldehyde, 4-nitrobenzoic acid, 4,4-azoxybenzoic acid and 2-amino-1-(4-nitrophenyl) propane-1,3-diol, as indicated by thin layer chromatography (Shih, 1971). Later work concerning the quality control of a pharmaceutical preparation (0.24% eye drops), it has found that under the influence of sunlight, some nitrosocompounds: p-nitrobenzene, p-nitrobenzaldehyde and pnitrosobenzoic acid are formed.…”

Section: Introductionmentioning

confidence: 99%

Potency and Antibacterial Efficacy of Degraded Chloramphenicol in Marketed Eye Drop Preparations

et al. 2015

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This study was done to evaluate the antibacterial activity of chloramphenicol eye drops after exposure to sunlight as well as to measure the percentage of drug content. Chloramphenicol eye drops manufactured by four different companies were collected from local market and exposed to sunlight and their antimicrobial activity was determined against Salmonella typhi and Staphylococcus aureus. Each product was exposed to sunlight for fourteen hours in three different ways with or without of their packaging. The percentage of chloramphenicol contents in eye drop samples was also measured by UV-spectrophotometric method. Significant differences in the inhibitory zones were observed among different set of samples. An inverse correlation between percentage of chloramphenicol content and their antibacterial activity was observed. The results indicate that the UVspectrophotometric method cannot distinguish between chloramphenicol and its degraded products and thus gives incorrect high values of drug content in the preparations, therefore, it should not be considered as an appropriate method to analyze chloramphenicol preparation with its degradation products.

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Degradation Products of Chloramphenicol

Cited by 14 publications

References 2 publications

Tuning the Kinetic Stability of the Amorphous Phase of the Chloramphenicol Antibiotic

Tuning the Kinetic Stability of the Amorphous Phase of the Chloramphenicol Antibiotic

Isolation, identification and characterization of human intestinal bacteria with the ability to utilize chloramphenicol as the sole source of carbon and energy

Potency and Antibacterial Efficacy of Degraded Chloramphenicol in Marketed Eye Drop Preparations

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