Physicochemical properties of the fluoroquinolone antimicrobials VI. Effect of metal-ion complexation on octan-1-ol-water partitioning

Ross, Danna L.; Elkinton, Steven K.; Knaub, Sheila R.; Riley, Christopher M.

doi:10.1016/0378-5173(93)90171-b

Cited by 25 publications

(7 citation statements)

References 21 publications

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“…This means that the reduction of the gastric absorption of lomefloxacin at co-administration with these metal ions, are not caused by the precipitation, but by a decrease of the octanol-water partition cofficient. Only for Bi 3+ , solubility and thus absorption of lomefloxacin, decresed as a result of formation of species with low solubility [143]. The permeability through intestinal mucosa of fluoroquinolone alone and in the presence of metal ions was studied in vitro .…”

Section: Consequences and Applications Of Metal-quinolone Complexamentioning

confidence: 99%

Metal Complexes of Quinolone Antibiotics and Their Applications: An Update

2013

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Quinolones are synthetic broad-spectrum antibiotics with good oral absorption and excellent bioavailability. Due to the chemical functions found on their nucleus (a carboxylic acid function at the 3-position, and in most cases a basic piperazinyl ring (or another N-heterocycle) at the 7-position, and a carbonyl oxygen atom at the 4-position) quinolones bind metal ions forming complexes in which they can act as bidentate, as unidentate and as bridging ligand, respectively. In the polymeric complexes in solid state, multiple modes of coordination are simultaneously possible. In strongly acidic conditions, quinolone molecules possessing a basic side nucleus are protonated and appear as cations in the ionic complexes. Interaction with metal ions has some important consequences for the solubility, pharmacokinetics and bioavailability of quinolones, and is also involved in the mechanism of action of these bactericidal agents. Many metal complexes with equal or enhanced antimicrobial activity compared to the parent quinolones were obtained. New strategies in the design of metal complexes of quinolones have led to compounds with anticancer activity. Analytical applications of complexation with metal ions were oriented toward two main directions: determination of quinolones based on complexation with metal ions or, reversely, determination of metal ions based on complexation with quinolones.

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Section: Consequences and Applications Of Metal-quinolone Complexamentioning

confidence: 99%

Metal Complexes of Quinolone Antibiotics and Their Applications: An Update

2013

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“…In addition, the performance of many pharmaceutical compounds in vivo may be strongly influenced by changing solution conditions, such as ionic strength, and by interactions with other compounds (e.g., (9)(10)(11)(12)(13)(14)(15)). As such, it is reasonable to hypothesize that all of these factors may influence the environmental behavior of many pharmaceuticals.…”

Section: Introductionmentioning

confidence: 99%

Effects of pH and Cationic and Nonionic Surfactants on the Adsorption of Pharmaceuticals to a Natural Aquifer Material

Hari

Paruchuri

Sabatini

et al. 2005

Environ. Sci. Technol.

155

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A wide range of pharmaceutical compounds have been identified in the environment, and their presence is a topic of growing concern, both for human and ecological health. Adsorption to aquifer materials and sediments is an important factor influencing the fate and transport of pharmaceutical compounds in the environment. Surfactants and other amphiphiles are known to influence the adsorption of many compounds and may be present in the environment from wastewaters or other sources. The work described here examines the adsorption of four pharmaceutical compounds, acetaminophen, carbamazepine, nalidixic acid, and norfloxacin, in the presence of a natural aquifer material. Adsorption was studied as a function of pH and in the presence and absence of two surfactants, cetylpyridinium chloride (CPC), a cationic surfactant, and Tergitol NP9, an ethoxylated nonionic surfactant. In the absence of surfactants, results indicate a 1-2 orders of magnitude variation in adsorption affinity with changing pH for each of the two quinolone pharmaceuticals (nalidixic acid and norfloxacin) but no measurable adsorption for carbamazepine or acetaminophen. In the presence of surfactants, adsorption of acetaminophen and carbamazepine was enhanced to extents consistent with compound hydrophobicity, while adsorption of nalidixic acid and norfloxacin was not. At high pH values, the anionic species of nalidixic acid exhibited enhanced adsorption in the presence of the cationic surfactant, CPC.

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“…This has resulted in therapeutic failure in at least one instance (11). The exact mechanism of this interaction has not been elucidated fully, although complexation with the metal ions (13)(14)(15) and adsorption to the antacids (19,20) are suggested mechanisms.…”

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confidence: 99%

“…It is generally accepted, therefore, that most multivalent cations decrease the oral bioavailability of the fluoroquinolones (11). The reduction in fluoroquinolone bioavailability in the presence of Ca2+, Mg2+, Fe2+, and Al3`ions has been explained on the basis of a decrease in lipophilicity of the fluoroquinolones following complexation with these ions compared with the lipophilicity of the uncomplexed drug (13). The interaction probably occurs between the cation and the 4-keto oxygen and 3-carboxylic acid groups (11,14).…”

mentioning

confidence: 99%

“…The interaction probably occurs between the cation and the 4-keto oxygen and 3-carboxylic acid groups (11,14). The degree of interaction appears to be dependent on the solubility and nature of the interacting metal cation-containing agents, the pH at the site of interaction, the fluoroquinolone structure, and the solubility and stability of the cation-quinolone complex (13)(14)(15). Additionally, the quinolones adsorb to antacids (19,20) containing compounds and ciprofloxacin in small numbers of subjects have resulted in less than a 30% decrease in the bioavailability of ciprofloxacin (2,18).…”

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confidence: 99%

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Effect of bismuth subsalicylate on ciprofloxacin bioavailability

Rambout¹,

Sahai²,

Gallicano³

et al. 1994

Antimicrob Agents Chemother

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A single oral dose of 528 mg of bismuth subsalicylate (30 ml of Pepto-Bismol) had no significant elect on the plasma pharmacokinetics of a single oral dose of 750 mg of ciprofloxacin administered to 12 healthy volunteers (six men and six women). These results suggest that ciprofloxacin bioavailability will not be significantly decreased by single doses of bismuth subsalicylate when the two medications are administered simultaneously.Development of the fluoroquinolones has allowed oral treatment of serious infections which until a few years ago required parenteral therapy (8). Although many of these agents are absorbed well from the gastrointestinal tract, their bioavailability is reduced significantly when administered with antacids containing di-and trivalent metal cations (10,12,16,17). This has resulted in therapeutic failure in at least one instance (11). The exact mechanism of this interaction has not been elucidated fully, although complexation with the metal ions (13-15) and adsorption to the antacids (19, 20) are suggested mechanisms.Bismuth, a heavy metal, can exist as a trivalent cation. Bismuth subsalicylate (Pepto-Bismol) is commonly used for the symptomatic treatment and prevention of a variety of gastrointestinal disorders. Bismuth subsalicylate decreases the bioavailability of tetracyclines significantly, and recommendations have been made for separation of the dosing times for these two medications (1, 4). However, preliminary studies evaluating the interaction of bismuth salts on norfloxacin and ciprofloxacin absorption have demonstrated only minor reductions in fluoroquinolone bioavailability (3,18). These data are in distinct contrast to those observed when ciprofloxacin is administered concurrently with other trivalent cations, such as aluminum. Because patients are likely to receive bismuthcontaining compounds concurrently with fluoroquinolones, among which ciprofloxacin is well established, this study was conducted to determine the effect of a single dose of bismuth subsalicylate on ciprofloxacin absorption in healthy volunteers.This study was approved by the Human Experimental Procedures Committee, Ottawa General Hospital, Ottawa, Ontario, Canada. Written informed consent was obtained from 12 healthy volunteers (six men and six women). The mean (± standard deviation) age and weight of the subjects were 35 ± 8 years and 70 ± 11 kg, respectively. Volunteers were excluded on the basis of the following: pregnancy, hypersensitivity reactions to any drug, use of any medications, chronic illness, current infection, abnormal finding on physical examination, abnormal renal or hepatic function tests, and abnormal hematology or urinalysis. On the morning of each study day, subjects were admitted to the Clinical Investigation Unit, Ottawa General Hospital.The study design was a randomized, two-period, two-treat- ment, two-sequence crossover with a 7-day washout period. Subjects were instructed to fast overnight and were not allowed to eat until 4 h after administration of the study medications. In on...

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Physicochemical properties of the fluoroquinolone antimicrobials VI. Effect of metal-ion complexation on octan-1-ol-water partitioning

Cited by 25 publications

References 21 publications

Metal Complexes of Quinolone Antibiotics and Their Applications: An Update

Metal Complexes of Quinolone Antibiotics and Their Applications: An Update

Effects of pH and Cationic and Nonionic Surfactants on the Adsorption of Pharmaceuticals to a Natural Aquifer Material

Effect of bismuth subsalicylate on ciprofloxacin bioavailability

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