Metabolism in Rats and Man of Piromidic Acid, a New Antibacterial Agent

Sekine, Yutaka; Miyamoto, Mie; Hashimoto, Masahisa; Nakamura, Kiyoshi

doi:10.3109/00498257609151628

Cited by 13 publications

(1 citation statement)

References 14 publications

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“…Although also found in bile and excreta, IV-demethyl danofloxacin was not detected in muscle or fat/skin, indicating that it is an excretory metabolite. The formation of IV-demethyldanofloxacin is not unexpected given the results of numerous metabolism studies of quinolones (Sekine et al, 1976;Edelson et al, 1977;Nagatsu et al, 1981a,b;Sudo et al, 1986;Gau et al, 1986;Borner and Lode, 1986; Outman and Nightingale, 1989).…”

Section: Discussionmentioning

confidence: 93%

Residue depletion studies on danofloxacin in the chicken

Lynch¹,

Rice²,

Ericson³

et al. 1994

J. Agric. Food Chem.

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Penetration of danofloxacin into tissues is consistent with oral bioavailability and pharmacokinetic plasma data derived from chickens given danofloxacin by iv bolus and oral gavage administration at 5 mg/kg. This pharmacokinetic assessment was confirmed when [3H]danofloxacin was administered to broilers in drinking water at 25 /ug/mL for 5 days, and tissues were assayed for residues. Under this regimen, total residues of danofloxacin were higher in liver than other tissues and declined in liver from 0.612 jug/g at 6 h to 0.056 gg/g by 48 h of withdrawal, suggesting rapid depletion. In kidney and muscle total residues depleted in parallel with liver but were 2-and 10-fold lower, respectively. The major residue in all tissues was unchanged danofloxacin. An /V-demethyl metabolite was found in liver and excreta but was not detected in muscle or fat/skin, indicating that it is an excretory metabolite. The depletion of unchanged and /V-demethyl metabolite residues from edible tissues of the chicken was confirmed by HPLC with fluorescence detection when danofloxacin was given to 3-week-old chickens under a commercial use condition, i.e., in drinking water for 3 days at 5 mg/kg of body weight per day.

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Section: Discussionmentioning

confidence: 93%

Residue depletion studies on danofloxacin in the chicken

Lynch¹,

Rice²,

Ericson³

et al. 1994

J. Agric. Food Chem.

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Mechanistic aspects of oxidation of N‐substituted 5H‐dibenz[c,e]azepines by aldehyde oxidase

Thomas

Ruenitz

1984

Journal of Heterocyclic Chem

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5H‐Dibenz[c,e]azepine (2) and its N‐ethyl and N‐(2‐ethoxyethyl) analogues 3 and 4 were prepared and evaluated as substrates for aldehyde oxidase. Quaternization of 2 with ethyl iodide furnished 3, while 4 was prepared by lithium aluminum hydride reduction of N‐(2‐ethoxy)ethyldiphenimide followed by mercuric acetate oxidation of the resultant amine 6. The rates of oxidation of 2 and 3 were similar, suggesting a lack of selectivity by the enzyme for the respective imine and iminium functional groups in these compounds. The rate of oxidation of 3 decreased with increasing pH while the extent of “hydration” of this substrate increased over a similar pH range, signifying a preference by the enzyme for 3 over its carbinolamine equilibrium partner. Experiments with deuterium labelled analogues of 2 and 3 indicated that azomethine hydrogen loss from these substrates during enzymatic oxidation was not rate determining. Thus 5H‐dibenz[c,e]azepine‐5,5,7‐d3 (7), prepared by lithium aluminum deuteride reduction of diphenimide (5), and its N‐ethyl analogue 8, had respective enzymatic oxidation rates which did not differ from those of their non‐deuterated counterparts.

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Synthesis of antimicrobial agents. II. Syntheses and antibacterial activities of optically active 7‐(3‐hydroxypyrrolidin‐1‐yl)quinolones

Uno¹,

Iuch²,

Kawahata³

et al. 1987

Journal of Heterocyclic Chem

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Two optically active isomers of 1‐ethyl‐6,8‐difluoro‐1,4‐dihydro‐7‐(3‐hydroxypyrrolidin‐1‐yl)‐4‐oxoquinoline‐3‐carboxylic acid (10) were prepared. One of the isomer, 7‐[(3S)‐hydroxypyrrolidin‐1‐yl] derivative 8, was about 4 times more potent in vitro than the other, 7‐[(3R)‐hydroxypyrrolidin‐1‐yl] derivative 4, and approximately two times more active than the racemate, 7‐[(3RS)‐hydroxypyrrolidine‐1‐yl] derivative 10. Optical active 8 was the most active in in vivo, followed by 10, and 4 was the least active compound. But, they were more potent than CI‐934 12 and norfloxacin. From the results, (3S)‐hydroxypyrrolidinyl group was found to be one of the beneficial group for PCA‐anti‐bacterial agent.

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Metabolism in Rats and Man of Piromidic Acid, a New Antibacterial Agent

Cited by 13 publications

References 14 publications

Residue depletion studies on danofloxacin in the chicken

Residue depletion studies on danofloxacin in the chicken

Mechanistic aspects of oxidation of N‐substituted 5H‐dibenz[c,e]azepines by aldehyde oxidase

Synthesis of antimicrobial agents. II. Syntheses and antibacterial activities of optically active 7‐(3‐hydroxypyrrolidin‐1‐yl)quinolones

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