Lipophilicity of antibacterial fluoroquinolones

Research output: Contribution to journalArticle

128 Citations (Scopus)

Abstract

The octanol/water partition coefficients of nine antibacterial fluoroquinolones and nalidixic and oxolinic acids were investigated. The pH-partition profile of amphoteric fluoroquinolones obtained between pH 4 and 10 showed maximum partitioning at the isoelectric point. From the two microspecies (zwitterionic and nonionic forms) which exist predominantly at this pH, the nonionic form is assumed to be transferred into the octanol phase. A relationship is derived between the apparent and true partition coefficients, valid for ampholyte compounds capable of forming zwitterions and having nonionic microspecies present in significant amounts. On the bases of true partition coefficients, three groups of examined fluoroquinolones are distinguished: lipophilic compounds (e.g., pefloxacin and amifloxacin), molecules of intermediate lipophilicity (such as ciprofloxacin and ofloxacin, etc.) and hydrophilic derivatives (e.g., norfloxacin and lomefloxacin, etc.). The influence of structural modification on the lipophilicity of these drugs is discussed.

Original languageEnglish
Pages (from-to)89-96
Number of pages8
JournalInternational Journal of Pharmaceutics
Volume79
Issue number1-3
DOIs
Publication statusPublished - Feb 1 1992

Fingerprint

Fluoroquinolones
Octanols
Oxolinic Acid
Pefloxacin
Norfloxacin
Nalidixic Acid
Ofloxacin
Isoelectric Point
Ciprofloxacin
Buffers
Water
Pharmaceutical Preparations

Keywords

  • Ampholyte
  • Apparent-true partition coefficient relationship
  • Fluoroquinolone
  • pH-partitioning behavior

ASJC Scopus subject areas

  • Pharmaceutical Science

Cite this

Lipophilicity of antibacterial fluoroquinolones. / Takács-Novák, K.; Józan, Miklós; Hermecz, I.; Szász, G.

In: International Journal of Pharmaceutics, Vol. 79, No. 1-3, 01.02.1992, p. 89-96.

Research output: Contribution to journalArticle

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