<abstract xmlns="http://www.w3.org/1999/xhtml"><p>The formation of salts is considered a simple strategy to modify the physicochemical properties of active pharmaceutical ingredients. In this study, seven novel binary and ternary organic salts of ciprofloxacin (CP) were prepared with benzoic acid (BA), acetylsalicylic acid (ASA), <italic>p</italic>-coumaric acid (PCMA) and <italic>p</italic>-aminosalicylic acid (PASA). They were characterized by spectroscopic techniques and differential scanning calorimetry. Solubility and partition coefficients values were also measured. Evaluation of the antimicrobial activity of the organic salts against <italic>Staphylococcus aureus</italic> and <italic>Staphylococcus epidermidis</italic> revealed that most of the new salts had higher antimicrobial activity than CPHCl against both strains. The most active compounds against <italic>S. epidermidis</italic> and <italic>S. aureus</italic> were CP-PASA and CPPCMA, resp., which were up to fourteen times more potent than parent CP-HCl. Our findings indicated a strong correlation between the lipophilicity of the formed salts and their antimicrobial activity and showed that an optimum value of lipophilicity (log <italic>P</italic> = 0.75) seemed to be necessary to maximize the antimicrobial activity. These findings highlighted the improved physical, thermal and antimicrobial properties of the new salts of CP that can aid in providing higher bioavailability than CP-HCl.</p></abstract>

The formation of salts is considered a simple strategy to modify the physicochemical properties of active pharmaceutical ingredients. In this study, seven novel binary and ternary organic salts of ciprofloxacin (CP) were prepared with benzoic acid (BA), acetylsalicylic acid (ASA), p-coumaric acid (PCMA) and p-aminosalicylic acid (PASA). They were characterized by spectroscopic techniques and differential scanning calorimetry. Solubility and partition coefficients values were also measured. Evaluation of the antimicrobial activity of the organic salts against Staphylococcus aureus and Staphylococcus epidermidis revealed that most of the new salts had higher antimicrobial activity than CPHCl against both strains. The most active compounds against S. epidermidis and S. aureus were CP-PASA and CPPCMA, resp., which were up to fourteen times more potent than parent CP-HCl. Our findings indicated a strong correlation between the lipophilicity of the formed salts and their antimicrobial activity and showed that an optimum value of lipophilicity (log P = 0.75) seemed to be necessary to maximize the antimicrobial activity. These findings highlighted the improved physical, thermal and antimicrobial properties of the new salts of CP that can aid in providing higher bioavailability than CP-HCl.

Preparation, characterization and antimicrobial assessment of selected ciprofloxacin salts

Department of Pharmaceutical Sciences School of Pharmacy

Department of Pharmaceutics and Pharmaceutical Technology, School of Pharmacy

Acta Pharmaceutica

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

The formation of salts is considered a simple strategy to modify the physicochemical properties of active pharmaceutical ingredients. In this study, seven...

Preparation, characterization and antimicrobial assessment of selected ciprofloxacin salts

Published Online: Dec 31, 2020

Page range: 365 - 382

Accepted: Sep 18, 2020

DOI: https://doi.org/10.2478/acph-2021-0028

Keywords
ciprofloxacin, salts, partition coefficient, Staphylococcus aureus, Staphylococcus epidermidis

© 2021 Imad I. Hamdan et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Preparation, characterization and antimicrobial assessment of selected ciprofloxacin salts

Published Online: Dec 31, 2020

Page range: 365 - 382

Accepted: Sep 18, 2020

DOI: https://doi.org/10.2478/acph-2021-0028

Keywordsciprofloxacin, salts, partition coefficient, Staphylococcus aureus, Staphylococcus epidermidis

© 2021 Imad I. Hamdan et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Keywords
ciprofloxacin, salts, partition coefficient, Staphylococcus aureus, Staphylococcus epidermidis