Effect of C-5 position on the photochemical properties and phototoxicity of antofloxacin and levofloxacin: A stable and transient study

Zhao, Jianfeng; Liu, Yancheng; Jiang, Xingxing; Guo, Ping; Yan, Xu; Zhang, Peng; Ji, Te; Lin, Zheshuai; Wang, Wenfeng

doi:10.1016/j.jphotobiol.2015.12.004

Cited by 17 publications

(22 citation statements)

References 57 publications

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“…Previous study found that antofloxacin relatively had more photostable and a weaker photosensitizer compared with levofloxacin. 21 The severities of adverse events in all the patients receiving ACLA and LCLA therapy were mild to moderate. There were rare severe adverse events in the ACLA group except that 2 patients had severe adverse events of headache and vomiting.…”

Section: Discussionmentioning

confidence: 89%

“…Antofloxacin, new-generation quinolones, is an improved version of LEV with an extra-NH2 group in the C-5 position which was invented in China in the late 1990s and approved in 2009. 21 Antofloxacin have been continuously and intensively studied to remedy this situation and develop antibiotics exhibiting high potency, long half-lives of elimination, few adverse effects, and low risk of drug resistance. 22 Our findings verify the previously reported, satisfactory results without the serious problem of resistance as levofloxacin.…”

Section: Discussionmentioning

confidence: 99%

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Antofloxacin, a novel fluoroquinolone, as a component of bismuth quadruple therapy for Helicobacter pylori eradication: a prospective, open-label, randomized trial

He¹,

Wang²,

Li³

et al. 2020

Preprint

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Background Currently, the eradication rate of Helicobacter pylori ( H. pylori ) is markedly decreasing due to some antibiotics resistance, including clarithromycin, metronidazole, and levofloxacin. So, there is a considerable interest in evaluating new antibiotic combinations and regimens. Antofloxacin is a novel fluoroquinolone with broad-spectrum antibacterial activity against Gram-negative bacilli including H. pylori . This study is designed to evaluate the efficacy, safety and tolerability of 14-day antofloxacin-based bismuth quadruple therapy as a treatment regimen in Chinese patients with H. pylori infection. Methods We recruited 290 adult patients with H. pylori infection through upper endoscopy and histologic examination. Patients were randomly assigned to receive either antofloxacin-based bismuth quadruple therapy (ACLA therapy, antofloxacin 200 mg once daily, colloidal bismuth pectin 200 mg three times a day, lansoprazole 30 mg twice daily, and amoxicillin 1 g twice daily) for 14 days; or levofloxacin-based bismuth quadruple therapy (LCLA therapy, levofloxacin 500 mg once daily, colloidal bismuth pectin 200 mg three times a day, lansoprazole 30 mg twice daily, and amoxicillin 1 g twice daily) for 14 days. Eradication was assessed by 13 C-urea breath test after six-week treatment, the primary endpoint was the eradication rate by intention-to-treat (ITT) and per-protocol (PP) analyses. Results Allocated to ACLA were 145 (66F/70M, 42.1±12.8 years, 19.3% smokers, 13.1% alcohol drinker) and 145 (64F/81M, 41.1±12.2 years, 17.9% smokers, 12.4% alcohol drinker) patients to LCLA. 13 patients were lost to follow-up and 3 patients took < 80% of treatment drugs. The resistant rates for amoxicillin, levofloxacin and antofloxaci were 4.1% (12/290), 30.3% (44/145) and 0% (0/145), respectively. The ITT analysis showed eradication rates were 93.8% (136/145) in the ACLA group versus 86.2% (125/145) in the LCLA group ( p =0.031). The PP analysis showed eradication rates were 97.8% (136/139) in the ACLA group versus 92.6% (125/135) in the LCLA group ( p =0.000). The ACLA therapy exhibited lower rates of overall adverse events than LCLA therapy (33.8% vs. 42.0%), but the difference was not statistically significant ( p =0. 159). Conclusion Antofloxacin-based bismuth quadruple therapy might be considered as an alternative for the eradication of H. pylori treatment, since it attained a successful eradication rate of 90% which was superior than levofloxacin-based bismuth quadruple therapy. Both regimens were well tolerated and safe.

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Section: Discussionmentioning

confidence: 89%

Section: Discussionmentioning

confidence: 99%

Antofloxacin, a novel fluoroquinolone, as a component of bismuth quadruple therapy for Helicobacter pylori eradication: a prospective, open-label, randomized trial

He¹,

Wang²,

Li³

et al. 2020

Preprint

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“…As shown in Chart , the substituent at the ortho-position for 1 and 2 is H atom and NH 2 , respectively, which is the only structural difference for 1 and 2 . However, these two compounds display distinct photochemical and phototoxic behaviors . Furthermore, many issues related to the reaction mechanisms are unclear for 1 and 2 .…”

Section: Introductionmentioning

confidence: 99%

“…However, these two compounds display distinct photochemical and phototoxic behaviors. 24 ■ EXPERIMENTAL DETAILS Materials. Levofloxacin (LEV, >98.0% purity) was commercially obtained from Sigma Chemicals and used as received.…”

Section: ■ Introductionmentioning

confidence: 99%

Photophysical Properties Controlled by Substituents with Lone-Pair Electrons at the Ortho- or Para-Positions of Fluoroquinolone Antibiotics

et al. 2019

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The ortho- or para-substituents of NH2 or N-alkyl-containing lone-pair electrons were found to change the energy levels and transition configurations of the highest occupied molecular orbital for some fluoroquinolone-based antibiotics (FQs) and can significantly influence the electronic structure, intermolecular hydrogen bonding, internal conversion, and fluorescence and intersystem crossing efficiencies of FQs in acetonitrile or aqueous solution after photoexcitation. These findings provide new insights that can help in the molecular design strategies to regulate the photophysical properties of photosensitive medicines, photodynamic therapy reagents, and energy conversion materials that contain similar aromatic carbonyl structures.

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“…Fluoroquinolones (FQs) have been widely used for decades because of their efficient and broad-spectrum antibacterial activity. , Antofloxacin (CAS no. 119354-43-7) is a novel fluoroquinolone that has been approved in China. , Figure shows the chemical structure of antofloxacin.…”

Section: Introductionmentioning

confidence: 99%

Research on Dissolution Capability of Several Antofloxacin Salts

Dong

Qiao

et al. 2018

J. Chem. Eng. Data

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The solubilities of three antofloxacin salts (antofloxacin hydrochloride, antofloxacin sulfate, and antofloxacin succinate) in six organic solvents, including methanol, ethanol, n-propanol, n-butanol, acetonitrile, and N,N-dimethylformamide (DMF), were determined experimentally over a temperature range from 273.15 to 318.15 K under 101.3 kPa. Within the temperature range studied, the solubility of these three compounds in the solvents increased with a rise of temperature. The solubility values of antofloxacin hydrochloride in these six solvents obey the following order: (methanol, DMF) > n-butanol > ethanol > n-propanol > acetonitrile. For the systems of antofloxacin sulfate + solvents, it ranked as DMF > methanol > ethanol > acetonitrile > n-propanol > n-butanol. While for antofloxacin succinate + solvents, the order of the data from high to low is DMF > methanol > n-butanol > n-propanol > ethanol > acetonitrile. The solubility data obtained for these three compounds in the studied solvents were correlated by using the modified Apelblat and λh equations. The maximum values of root-mean-square deviation (RMSD) and relative average deviation (RAD) were 3.3 × 10 −5 and 4.06%, respectively. Generally, the RAD values acquired with the modified Apelblat equation were smaller than λh equation for a certain solvent. The two thermodynamic models were all acceptable for the systems of these three compounds in these solvents. The obtained solubility values would be very helpful for drug application of antofloxacin hydrochloride, antofloxacin sulfate, and antofloxacin succinate.

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Effect of C-5 position on the photochemical properties and phototoxicity of antofloxacin and levofloxacin: A stable and transient study

Cited by 17 publications

References 57 publications

Antofloxacin, a novel fluoroquinolone, as a component of bismuth quadruple therapy for Helicobacter pylori eradication: a prospective, open-label, randomized trial

Antofloxacin, a novel fluoroquinolone, as a component of bismuth quadruple therapy for Helicobacter pylori eradication: a prospective, open-label, randomized trial

Photophysical Properties Controlled by Substituents with Lone-Pair Electrons at the Ortho- or Para-Positions of Fluoroquinolone Antibiotics

Research on Dissolution Capability of Several Antofloxacin Salts

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