Thermal study and characterization of new cocrystals of ciprofloxacin with picolinic acid

Torquetti, Carolina; Ferreira, Patrícia Osório; Almeida, Amanda Cosmo de; Fernandes, Richard Perosa

doi:10.1007/s10973-020-10479-3

Cited by 6 publications

(6 citation statements)

References 24 publications

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“…The IR spectra of extruded samples and the initial precursors were obtained in order to identify the possible intermolecular interactions and the extent of cocrystal formation for samples extruded using conveying and kneading screw configurations (Figures 11 and A1). The IR spectrum of CIP was similar to the data available in the literature [41,48]. The presence of strong bands between 1702 cm −1 (νC=Ocarbonyl) and 1623 cm −1 (δN-Hamine bending) and weak bands in the range of 2580-2680 cm −1 that are related to the presence of ν NH 2+ group confirmed the presence of CIP in the zwitterionic form [49].…”

Section: Fourier Transform Infrared Spectroscopy (Ftir)supporting

confidence: 81%

“…Moreover, ciprofloxaine hydrochloride has been classified as BCS class IV [ 30 ]. Several attempts for tackling CIP’s low aqueous solubility issue include salt formation [ 26 , 29 , 31 , 32 , 33 , 34 , 35 , 36 ] and amorphization [ 23 ] with less frequent cases of cocrystallization [ 36 , 37 , 38 , 39 , 40 , 41 ]. As an example, Martinez-Alejo et al studied the cocrystal of ciprofloxacin and moxifloxacin hydrochloride salts with 4-hydroxybenzoic acid as coformer.…”

Section: Introductionmentioning

confidence: 99%

“…They showed that both NG and LAG methodologies were applicable when forming the cocrystal of CIP–PZCA, but for CIP–PABA, only the LAG approach led to the formation of cocrystal. Moreover, they demonstrated the feasibility of formation of CIP cocrystal with picolinic acid (PCA) in 1:1 molar ratio via LAG, with an increase of 27% in solubility of CIP compared with the pure form of the drug [ 41 ]. In another study, nicotinic (NCA) and isonicotinic acid (INCA) were selected as coformer with CIP as API to study cocrystal formation.…”

Section: Introductionmentioning

confidence: 99%

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Formation of Ciprofloxacin–Isonicotinic Acid Cocrystal Using Mechanochemical Synthesis Routes—An Investigation into Critical Process Parameters

et al. 2022

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The mechanochemical synthesis of cocrystals has been introduced as a promising approach of formulating poorly water-soluble active pharmaceutical ingredients (APIs). In this study, hot-melt extrusion (HME) as a continuous process and grinding and ball milling as batch processes were employed to explore the feasibility of cocrystallization. Ciprofloxacin (CIP) and isonicotinic acid (INCA) were selected as the model API and coformer. CIP–INCA cocrystal was produced in all techniques. It was revealed that higher cocrystal content could be achieved at longer durations of grinding and ball milling. However, milling for more than 10 min led to increased co-amorphous content instead of cocrystal. A design of experiment (DoE) approach was used for deciphering the complex correlation of screw configuration, screw speed, and temperature as HME process parameters and their respective effect on final relative cocrystal yield. Statistical analysis showed that screw configuration, temperature, and their interaction were the most critical factors affecting cocrystallization. Interestingly, screw speed had minimal impact on the relative cocrystallization yield. Cocrystallization led to increased dissolution rate of CIP in phosphate buffer up to 2.5-fold. Overall, this study shed a light on the potential of mechanochemical synthesis techniques with special focus on HME as a continuous process for producing cocrystals.

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Section: Fourier Transform Infrared Spectroscopy (Ftir)supporting

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Formation of Ciprofloxacin–Isonicotinic Acid Cocrystal Using Mechanochemical Synthesis Routes—An Investigation into Critical Process Parameters

et al. 2022

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“…The most notable reactions were oxidation, reduction, hydrolysis, and aromatic ring destruction. It was hypothesized that heating treatment may expedite these processes, thereby decreasing the picolinic acid content in egg yolks [ 51 ]. Additionally, boiling reduced the content of pc(18:1(11z)/14:0) in the yolks of captive mallards and Shaoxing ducks.…”

Section: Discussionmentioning

confidence: 99%

Integration of LC-MS-Based and GC-MS-Based Metabolic Profiling to Reveal the Effects of Domestication and Boiling on the Composition of Duck Egg Yolks

Tian

et al. 2023

Metabolites

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Egg yolks contain abundant lipids, proteins, and minerals that provide not only essential nutrients for embryonic development but also cheap sources of nutrients for consumers worldwide. Previous composition analyses of egg yolks primarily focused on nutrients such as lipids and minerals. However, few studies have reported the effects of domestication and heating on yolk composition and characteristics. The objective of this study was to investigate the impact of domestication and boiling on the metabolite contents of egg yolks via untargeted metabolomics using GC-MS and LC-MS. In this study, eggs were collected from Fenghua teals, captive mallards, and Shaoxing ducks. Twelve duck eggs (half raw and half cooked) were randomly selected from each variety, and the egg yolks were separated for metabolic profiling. The analysis identified 1205 compounds in the egg yolks. Domestication generated more differential metabolites than boiling, which indicated that the changes in the metabolome of duck egg yolk caused by domestication were greater than those caused by boiling. In a comparative analysis of domestic and mallard ducks, 48 overlapping differential metabolites were discovered. Among them, nine metabolites were upregulated in domesticated ducks, including monoolein, emodin, daidzein, genistein, and glycitein, which may be involved in lipid metabolism; some of them may also act as phytoestrogens (flavonoids). Another 39 metabolites, including imethylethanolamine, harmalan, mannitol, nornicotine, linoleic acid, diphenylamine, proline betaine, alloxanthin, and resolvin d1, were downregulated by domestication and were linked to immunity, anti-inflammatory, antibacterial, and antioxidant properties. Furthermore, four overlapping differential metabolites that included amino acids and dipeptides were discovered in paired comparisons of the raw and boiled samples. Our findings provided new insights into the molecular response of duck domestication and supported the use of metabolomics to examine the impact of boiling on the composition of egg yolks.

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“…For example, ciprofloxacin combined with non-steroidal anti-inflammatory drugs (NSAIDs) to improve both side's physicochemical properties, i.e., solubility [ 12 ]. Interestingly, some antibiotic multi-components show better antimicrobial activity than their parent drug, such as ciprofloxacin – picolinic acid [ 13 ] and ciprofloxacin – thiobarbituric and barbituric acid [ 14 ]. Next, some authors reported LF - metacetamol [ 15 ] and stearic acid [ 16 ], which improved LF's photostability and hygroscopicity and masked its unpleasant taste.…”

Section: Introductionmentioning

confidence: 99%

New proportion of levofloxacin citrate: Structural, physicochemical properties, and potency studies

Nugrahani,

Uekusa,

Oyama

et al. 2024

Heliyon

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Thermal study and characterization of new cocrystals of ciprofloxacin with picolinic acid

Cited by 6 publications

References 24 publications

Formation of Ciprofloxacin–Isonicotinic Acid Cocrystal Using Mechanochemical Synthesis Routes—An Investigation into Critical Process Parameters

Formation of Ciprofloxacin–Isonicotinic Acid Cocrystal Using Mechanochemical Synthesis Routes—An Investigation into Critical Process Parameters

Integration of LC-MS-Based and GC-MS-Based Metabolic Profiling to Reveal the Effects of Domestication and Boiling on the Composition of Duck Egg Yolks

New proportion of levofloxacin citrate: Structural, physicochemical properties, and potency studies

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