Fluoroquinolone antibacterial drugs: Review of physicochemical problems, analysis techniques, and solutions
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Abstract
Fluoroquinolones are a class of second-generation quinolone antibiotics. Some fluoroquinolone drugs have problems concerning their photostability. There are also problems of physicochemical properties related to hygroscopicity, incompatibility with its excipient during formulation, and interactions with other drugs. Efforts to increase photostability and reduce hygroscopicity continue, as do efforts to solve the problem of incompatibility with certain excipients and interactions with other drugs. If these issues are not resolved, they will cause problems during their manufacture and administration to patients, which will affect the therapeutic value of the drugs. Efforts to improve the stability of fluoroquinolones have been reported, such as preparing co-crystals and complexes with polymers. This research has shown potential, but the challenge is to have a deeper understanding of the physicochemical characteristics of fluoroquinolone drugs have insight into other problem-solving approaches with respect to the composition of the formula, the manufacturing process, equipment, and even packaging used in formulating the drug. A deeper understanding the problems will lead to appropriate solutions, such as improving photostability, reducing hygroscopicity, choosing excipients during formulation, and using the correct drug.
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References
Ebimieowei E, Ibemologi A. Antibiotics: classification and mechanisms of action with emphasis on molecular perspectives. Int J Appl Microbiol Biotechnol Res. 2016;4:90-101.
Pham TDM, Ziora ZM, Blaskovich MAT. Quinolone antibiotics. Med Chem Comm. 2019;10:1719-1739.
Zhanel GG, Ennis K, Vercaigne L, Walkty A, Gin AS, Embil J, et al. Fluoroquinolones focus on respiratory tract infections. Drugs. 2002;62:13-59.
Suzuki T, Terada K. Elucidation of the crystal structure-physicochemical property relationship among polymorphs and hydrates of sitafloxacin, a novel fluoroquinolone antibiotic. Int J Pharm. 2012;422(1-2):1-8.
Budai M, Gróf P, Zimmer A, Pápai K, Klebovich I, Ludányi K. UV light induced photodegradation of liposome encapsulated fluoroquinolones: an MS study. J Photochem Photobiol A Chem. 2008;198:268-273.
Shinozaki T, Ono M, Higashi K, Moribe K. A novel drug-Drug cocrystal of levofloxacin and metacetamol: reduced hygroscopicity and improved photostability of levofloxacin. J Pharm Sci. 2019; 108(7):2383-2890.
Nisar J, Iqbal M, Iqbal M, Shah A, Akhter MS, Sirajuddin, et al. Decomposition kinetics of levofloxacin: drug-excipient interaction. Z Phys Chem. 2020;234(1):117-128.
Jolson HM. Adverse reaction reporting of interaction between warfarin and fluoroquinolones. Arch Intern Med. 1991;151(5):1003.
Rawashdeh AN, Shawakfeh K, Ata S. Photostability Study of ciprofloxacin with Cyclodextrins. Pure and Applied Chemistry International Conference (PACCON); 2008 30 Jan -1 Feb; Bangkok, Thailand. Bangkok: KU Sci Res; 2008. p. 416-421.
Boraste DR, Chakraborty G, Ray AK, Shankarling GS, Pal H. Supramolecular host-guest interaction of antibiotic drug ciprofloxacin with cucurbit[7]uril macrocycle: Modulations in photophysical properties and enhanced photostability. J Photochem Photobiol A Chem. 2018;358:26-37.
Ahmad I, Bano R, Sheraz MA, Ahmed S, Mirza T, Ansari SA. Photodegradation of levofloxacin in aqueous and organic solvents: a kinetic study. Acta Pharm. 2013;63(2):223-229.
Carlucci G. Analysis of fluoroquinolones in biological fluids by high-performance liquid chromatography. J Chromatogr A. 1998;812:343-367.
Ainurofiq A, Fajrin HI, Febriani, Fitriana A, Andriyani D. Preformulation study of solid dosage form to ensure a stable, efficacious, safe and comfortable product: a review. Int J Pharm Res. 2020;12:2762-2772.
Gorman EM, Samas B, Munson EJ. Understanding the dehydration of levofloxacin hemihydrate. J Pharm Sci. 2012;101(9):3319-3330.
Kitaoka H, Wada C, Moroi R, Hakusui H. Effect of dehydration on the formation of levofloxacin pseudopolymorphs. Chem Pharm Bull. 1995;43(4):649-653.
Hubicka U, Żmudzki P, Talik P, Witek ZB, Krzek J. Photodegradation assessment of ciprofloxacin, moxifloxacin, norfloxacin and ofloxacin in the presence of excipients from tablets by UPLC-MS/MS and DSC. Chem Cent J. 2013;7(1):133.
Vries H, Henegouwen GM. Photochemical decomposition of Lomefloxacin in vitro and in vivo. J Photochem Photobiol B Biol. 2000;58(1):6-12.
Hayashi N. New findings on the structure-phototoxicity relationship and photostability of fluoroquinolones. J Pharm Soc Jpn. 2005;125:255-261.
Zhao J, Liu Y, Jiang X, Guo P, Xu Y, Zhang P, et al. Effect of C-5 position on the photochemical properties and phototoxicity of antofloxacin and levofloxacin: a stable and transient study. J Photochem Photobiol B Biol. 2016;155:122-129.
Zhao JF, Liu YC, Xu YL, Wang WF. Effects of N-1 substituent on the phototoxicity of fluoroquinolone antibiotics: comparison of pefloxacin and difloxacin. Nucl Sci Tech. 2020;31(7):66.
Martínez LJ, Sik RH, Chignell CF. Fluoroquinolone antimicrobials: singlet oxygen, superoxide and phototoxicity. Photochem Photobiol. 1998;67(4):399-403.
Zahaby SA, Kassem AA, Kamel AH. Design and evaluation of gastroretentive levofloxacin floating mini-tablets-in-capsule system for eradication of helicobacter pylori. Saudi Pharm J. 2014;22(6):570-579.
Misra M, Misra AK, Panpalia GM, Dorle AK. Compatibility screening of some diluents with newer fluoroquinolone: moxifloxacin HCl. Pharm Res. 2011;2:9-17.
Oliveira PR, Bernardi LS, Murakami FS, Mendes C, Silva MAS. Thermal characterization and compatibility studies of norfloxacin for development of extended release tablets. J Therm Anal Calorim. 2009;97(2):741-745.
Spivey JM, Cummings DM, Pierson NR. Failure of prostatitis treatment secondary to probable ciprofloxacin-sucralfate drug interaction. Pharmacotherapy 1996;16(2):314-316.
Sudoh T, Fujimura A, Harada K, Sunaga K, Ohmori M, Sakamoto K. Effect of ranitidine on renal clearance of lomefloxacin. Eur J Clin Pharmacol. 1996;51:95-98.
Fish DN. Fluoroquinolone adverse effects and drug interactions. Pharmacotherapy 2001;21:1-4.
Teng R, Liston TE, Harris SC. Multiple-dose pharmacokinetics and safety of trovafloxacin in healthy volunteers. J Antimicrob Chemother. 1996;37(5):955-963.
Toon S, Hopkins KJ, Garstang FM, Aarons L, Sedman A, Rowland M. Enoxacin-warfarin interaction: Pharmacokinetic and stereochemical aspects. Clin Pharmacol Ther. 1987;42(1):33-41.
Frąckowiak A, Kamiński B, Urbaniak B, Dereziński P, Klupczyńska A, Duszkiewicz DM, et al. A study of ofloxacin and levofloxacin photostability in aqueous solutions. J Med Sci. 2016;85(4):238-244.
Lam MW, Mabury SA. Photodegradation of the pharmaceuticals atorvastatin, carbamazepine, levofloxacin, and sulfamethoxazole in natural waters. Aquat Sci. 2005;67(2):177-188.
Ainurofiq A, Choiri S. Drug release mechanism of slightly soluble drug from nanocomposite matrix formulated with zeolite/hydrotalcite as drug carrier. Trop J Pharm Res. 2015;14(7):1129-1135.
Otori T, Matzno S, Kawase A, Iwaki M, Kimachi T, Nishiwaki K, et al. Development of hemiacetal esterified levofloxacin to prevent chelation with metal-containing drugs. J Pharm Pharmacol. 2016; 68(12):1527-1534.
Fraix A, Afonso D, Consoli GML, Sortino S. A calix[4]arene-based ternary supramolecular nanoassembly with improved fluoroquinolone photostability and enhanced NO photorelease. Photochem Photobiol Sci. 2019;18:2216-2224.