Biowaiver Monographs for Immediate Release Solid Oral Dosage Forms: Ciprofloxacin Hydrochloride

Olivera, Marı́a Eugenia; Manzo, Rubén H.; Junginger, Hans E.; Midha, K. K.; Shah, Vinod P.; Stavchansky, Salomon A; Dressman, Jennifer B.; Barends, D. M.

doi:10.1002/jps.22259

Cited by 103 publications

(77 citation statements)

References 60 publications

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“…30 mg/ml at pH 11). Literature data point to 10-30 mg/ml water solubility for CIPRO HCl and 0.16-0.17 mg/ml solubility in PBS with pH ranging from 6.8 to 7.5 [26]. These data are in agreement with the experimental values for solubility of CIPRO obtained in the actual study.…”

Section: Solubilitysupporting

confidence: 88%

Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones

Breznica-Selmani

Mladenovska

Dräger

et al. 2016

Maced. J. Chem. Chem. Eng.

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Herein we report the synthesis of different derivatives of (fluoro)quinolones norfloxacin, ciprofloxacin and pipemidic acid, by incorporating (benzoylamino)methyl on the free nitrogen of the pyperazinyl moiety. The compounds were structurally characterized by 1D and 2D NMR, FTIR and highresolution mass spectroscopy. In addition, their physicochemical properties were a matter of interest to be correlated with their structure and antimicrobial activity in vitro. Their antimicrobial activities were screened against Gram-positive, Gram-negative bacteria and C. albicans. Higher distribution coefficients and consequently lower water solubility were determined for all synthesized compounds than the ones of the corresponding leading compounds. Inconsequential correlations between the lipophilicity of the compounds and MIC were observed, suggesting that passive diffusion is not the only mechanism for their penetration into bacterial cells. Further studies are needed to determine how substitutions in the (fluoro)quinolone moiety affect the primary target(s), substrate behavior in respect to bacterial transporters and overall bioavailability.Keywords: (benzoylamino)methyl; quinolones; structure; physicochemical properties; antimicrobial activity СИНТЕЗА, ФИЗИЧКОХЕМИСКА КАРАКТЕРИЗАЦИЈА И АНТИБАКТЕРИСКА АКТИВНОСТ НА НОВИ (БЕНЗОИЛАМИНО)МЕТИЛНИ ДЕРИВАТИ НА ХИНОЛОНИВо трудот е прикажана синтеза на различни деривати на (флуоро)хинолони со инкорпорирање на (бензоиламино)метилна група на слободниот азот од пиперазинскиот фрагмент кај норфлоксацинот, ципрофлоксацинот и пипемидинската киселина како водечки соединенија. Синтетизираните соединенија беа структурно карактеризирани со помош на 1D и 2D NMR, FTIR и масена спектрометрија со висока резолуција. Дополнително беа определени физичкохемиските особини на новосинтетизираните соединенија и корелирани со нивната структура и антимикро- 179-197 (2016) 180 бната активност in vitro. Антимикробната активност на новите соединенија беше испитувана на Gram-позитивни и Gram-негативни бактерии и на C. albicans. Сите новосинтетизирани соеди-ненија покажаа повисок коефициент на распределба и соодветно пониска растворливост во вода во однос на водечките соединенија. Корелациите меѓу липофилноста на синтетизираните соединенија и минималната инхибиторна концентрација (MIC) не беа статистички значајни, што укажува на тоа дека пасивната дифузија не е единствениот механизам со кој тие пенетрираат во бактериските клетки. Потребни се понатамошни истражувања за да се испита како супституциите во (флуоро)хинолонското јадро влијаат врз примарната цел(и), супстратното однесување во однос на бактериските транспортери и севкупната биорасположливост.

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Section: Solubilitysupporting

confidence: 88%

Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones

Breznica-Selmani

Mladenovska

Dräger

et al. 2016

Maced. J. Chem. Chem. Eng.

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“…Most fluoroquinolones are barely water soluble at a physiological pH; their solubilities increase at an acidic or alkaline pH, as fluoroquinolones are zwitterions. Ciprofloxacin hydrochloride, used in the liposomal formulation of ciprofloxacin, is moderately water soluble at pH 7 (54 to 86 mg/liter) (126)(127)(128), whereas ciprofloxacin betaine, used in the dry powder formulation, is "slightly soluble," i.e., Ͻ50 mg/liter (129). The water solubility of levofloxacin at pH 6.9 is a thousandfold higher, amounting to 50 g/liter, (130).…”

Section: Chemistry and Formulationmentioning

confidence: 99%

Pharmacokinetics and Pharmacodynamics of Aerosolized Antibacterial Agents in Chronically Infected Cystic Fibrosis Patients

Dalhoff¹

2014

Clin Microbiol Rev

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SUMMARY Bacteria adapt to growth in lungs of patients with cystic fibrosis (CF) by selection of heterogeneously resistant variants that are not detected by conventional susceptibility testing but are selected for rapidly during antibacterial treatment. Therefore, total bacterial counts and antibiotic susceptibilities are misleading indicators of infection and are not helpful as guides for therapy decisions or efficacy endpoints. High drug concentrations delivered by aerosol may maximize efficacy, as decreased drug susceptibilities of the pathogens are compensated for by high target site concentrations. However, reductions of the bacterial load in sputum and improvements in lung function were within the same ranges following aerosolized and conventional therapies. Furthermore, the use of conventional pharmacokinetic/pharmacodynamic (PK/PD) surrogates correlating pharmacokinetics in serum with clinical cure and presumed or proven eradication of the pathogen as a basis for PK/PD investigations in CF patients is irrelevant, as minimization of systemic exposure is one of the main objectives of aerosolized therapy; in addition, bacterial pathogens cannot be eradicated, and chronic infection cannot be cured. Consequently, conventional PK/PD surrogates are not applicable to CF patients. It is nonetheless obvious that systemic exposure of patients, with all its sequelae, is minimized and that the burden of oral treatment for CF patients suffering from chronic infections is reduced.

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“…Also, it cannot be taken for granted that each and every registered drug product has successfully met the current in vivo BE criteria. 78 Nevertheless, it seems safe to conclude that the risk of bioinequivalence caused by an excipient effect is low for excipients present in a large number of registered drug products, when the excipient is present in amounts not exceeding its normal use in IR tablets. Table 1 shows the range of that excipients present in solid oral dosage forms with a MA in the US.…”

Section: Excipientsmentioning

confidence: 99%

Biowaiver Monographs for Immediate Release Solid Oral Dosage Forms: Levofloxacin

Koeppe¹,

Cristofoletti²,

Fernandes³

et al. 2011

Journal of Pharmaceutical Sciences

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Biowaiver Monographs for Immediate Release Solid Oral Dosage Forms: Ciprofloxacin Hydrochloride

Cited by 103 publications

References 60 publications

Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones

Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones

Pharmacokinetics and Pharmacodynamics of Aerosolized Antibacterial Agents in Chronically Infected Cystic Fibrosis Patients

Biowaiver Monographs for Immediate Release Solid Oral Dosage Forms: Levofloxacin

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