Synthesis, Crystal Structure, and Hirshfeld Surface Analysis of Ciprofloxacin-Salicylic Acid Molecular Salt

Nagalapalli, Ravikumar; Bheem, Shankar Yaga

doi:10.1155/2014/936174

Cited by 6 publications

(4 citation statements)

References 21 publications

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“…In conclusion, in silico studies may produce a more accurate, greener, and comprehensive analysis, as shown by fluoroquinolones' multi-component systems, regarding their reactions with NSAIDs [26,30,153], metals [29], and furosemide [138]. This modeling approach simplifies the conventional experimental process of selecting the coformer and method, determining the structure, and testing properties, resulting in a more efficient approach [154,155]. Moreover, it also can predict changes in potency, as widely reported in the current decades.…”

Section: Computational Approach and Modeling For Multi-component Soli...mentioning

confidence: 99%

The Benefits and Challenges of Antibiotics–Non-Steroidal Anti-Inflammatory Drugs Non-Covalent Reaction

2023

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Recently, non-covalent reactions have emerged as approaches to improve the physicochemical properties of active pharmaceutical ingredients (API), including antibiotics and non-steroidal anti-inflammatory drugs (NSAIDs). This review aimed to present and discuss the non-covalent reaction products of antibiotics, including salt and neutral multi-component solid forms, by framing their substituents and molar ratios, manufacturing techniques, characterization methods, benefits, potency changes, and toxicity, and is completed with an analysis of the development of computational models used in this field. Based on the data, NSAIDs are the most-developed drugs in multi-component system preparations, followed by antibiotics, i.e., antituberculosis and fluoroquinolones. They have reacted with inorganic elements, excipients, nutraceuticals, natural products, and other drugs. However, in terms of treatments for common infections, fluoroquinolones are more frequently used. Generally, NSAIDs are acquired on an over-the-counter basis, causing inappropriate medication. In addition, the pKa differences between the two groups of medicine offer the potential for them to react non-covalently. Hence, this review highlights fluoroquinolone–NSAID multi-component solid systems, which offer some benefits. These systems can increase patient compliance and promote the appropriate monitoring of drug usage; the dual drug multi-component solids have been proven to improve the physicochemical properties of one or both components, especially in terms of solubility and stability. In addition, some reports show an enhancement of the antibiotic activity of the products. However, it is important to consider the possibility of activity changes, interaction, and toxicity when using drug combinations. Hence, these aspects also are discussed in this review. Finally, we present computational modeling, which has been utilized broadly to support multi-component system designs, including coformer screening, preparation methods, and structural modeling, as well as to predict physicochemical properties, potency, and toxicity. This integrated review is expected to be useful for further antibiotic–NSAID multi-component system development.

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Section: Computational Approach and Modeling For Multi-component Soli...mentioning

confidence: 99%

The Benefits and Challenges of Antibiotics–Non-Steroidal Anti-Inflammatory Drugs Non-Covalent Reaction

2023

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“…Several crystal structures of ciprofloxacin salts with benzoic acid derivatives have been reported, including salts with salicylic acid (Surov et al, 2019;Nagalapalli & Yaga Bheem, 2014; CSD refcode family DOFWUT), 4-hydroxybenzoic acid (Surov et al, 2020; CSD refcode PUNMUJ), 4-aminobenzoic acid (Surov et al, 2020; CSD refcode PUNMIX) and gallic acid (Surov et al, 2020;CSD refcode PUNMOD). A search for salt co-crystals of ciprofloxacin hydrochloride yielded one reported crystal structure, a co-crystal of ciprofloxacin hydrochloride with 4-hydroxybenzoic acid (Martı ´nez-Alejo et al, 2014; CSD refcode XOHTUL).…”

Section: Database Surveymentioning

confidence: 99%

Ciprofloxacin salt and salt co-crystal with dihydroxybenzoic acids

Nugraha¹,

Sugiyama²,

Uekusa³

2022

Acta Cryst E

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The crystal structure of two multi-component crystals of ciprofloxacin [systematic name: 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)quinoline-3-carboxylic acid], a fluoroquinolone antibiotic, namely, ciprofloxacin 2,6-dihydroxybenzoate salt, C17H19FN3O3 +·C7H5O4 −, (I), and ciprofloxacin hydrochloride–3,5-dihydroxybenzoic–water (1/1/1), C17H19FN3O3 +·Cl−·C7H6O4·H2O, (II), were determined. In (I) and (II), the ciprofloxacin cations are connected via head-to-tail N—H...O hydrogen bonding. Both structures show an alternating layered arrangement between ciprofloxacin and dihydroxybenzoic acid.

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“…Over the decades, multicomponent systems have been developed to modulate the physicochemical properties of active pharmaceutical ingredients (API), including fluoroquinolone antibiotics, such as ciprofloxacin [ 1 , 2 , 3 ] and levofloxacin (LF) [ 4 ]. In general, solid-structure development utilizes either ionic or non-ionic interactions or both [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

“…Solid multicomponent systems of fluoroquinolone with other drugs [ 1 , 2 , 3 , 19 ] and excipients [ 20 ] have been reported before. In addition, the combination of LF with phthalimide and caffeic acid has recently been reported to increase potency [ 21 ], as have other antibiotic solid multicomponent systems, such as azithromycin with paracetamol [ 22 ] and cefixime [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

Stability and Antibiotic Potency Improvement of Levofloxacin by Producing New Salts with 2,6- and 3,5-Dihydroxybenzoic Acid and Their Comprehensive Structural Study

et al. 2022

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Recently, solid-state engineering has become a promising approach to improving the stability and potency of antibiotics. Levofloxacin (LF) is a broad-spectrum fluoroquinolone antibiotic marketed in solid and solution dosage forms. However, this substance forms solid hydrates under ambient conditions and degrades due to lighting, which may change its solid properties and dose. In addition, resistance cases have been reported due to long-time antibiotic usage. This research aims to allow LF to react with antioxidant dihydroxybenzoic acid (DHBA), which has low antimicrobial activity, to produce a more stable compound under water and lighting conditions and improve LF’s potency. The experiment begins with a screening to select potential DHBA isomers that can react with LF and predict the stoichiometric ratio using phase diagrams, which show that 2,6-DHBA and 3,5-DHBA are prospective antioxidants that can react with LF in a (1:1) molar ratio. Multicomponent systems are prepared by dissolving the LF–DHBA mixture in (1:1) ethanol–methanol (95% grade) and evaporating it. Then, the new solid phase formation is confirmed by thermal analysis and powder X-ray diffractometry. Next, infrared spectrophotometry and neutron magnetic resonance analyses are used to identify the LF–DHBA’s interactions. Finally, single-crystal X-ray diffractometry is used to solve the three-dimensional structure of the multicomponent system. We then conduct a hygroscopicity and stability test followed by a lighting and potency test using the microdilution method. Our data reveal that both reactions produce salts, which are named LF-26 and LF-35, respectively. Structurally, LF-26 is found in an anhydrous form with a triclinic crystal packing, while LF-35 is a hemihydrate in a monoclinic system. Afterward, both salts are proven more stable regarding water adsorption and UV lighting than LF. Finally, both multicomponent systems have an approximately two-fold higher antibiotic potency than LF. LF-26 and LF-35 are suitable for further development in solid and liquid dosage formulations, especially LF-35, which has superior stability compared with LF-26.

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Synthesis, Crystal Structure, and Hirshfeld Surface Analysis of Ciprofloxacin-Salicylic Acid Molecular Salt

Cited by 6 publications

References 21 publications

The Benefits and Challenges of Antibiotics–Non-Steroidal Anti-Inflammatory Drugs Non-Covalent Reaction

The Benefits and Challenges of Antibiotics–Non-Steroidal Anti-Inflammatory Drugs Non-Covalent Reaction

Ciprofloxacin salt and salt co-crystal with dihydroxybenzoic acids

Stability and Antibiotic Potency Improvement of Levofloxacin by Producing New Salts with 2,6- and 3,5-Dihydroxybenzoic Acid and Their Comprehensive Structural Study

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