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Prodrugs pp 703-729 | Cite as

Prodrugs of Carboxylic Acids

  • Hans Maag
Part of the Biotechnology: Pharmaceutical Aspects book series (PHARMASP, volume V)

Abstract

Carboxylic acids are often present as a functional group of effective medicines. They are involved in specific charge-charge interactions and are thus often critical for the binding of agents to their targets. The carboxylic acid functional group adds to the hydrophilicity of the drug as well as to its polarity and this may impede the bioavailability. Most carboxylic acids have a pKa value of about 3.5 to 4.5 and thus these compounds are ionized (deprotonated) under physiological conditions. Quite often, the logD values of these agents drop below the range of logD values of well absorbed drugs (logD > 0). These properties of carboxylic acids in active principles has been well recognized for many years and a number of practical solutions have been identified with the most common one being that of the ester modification. This brief review will concentrate on successful prodrug strategies for carboxylic acids, with particular emphasis on compounds which have reached the market, and will not cover ester prodrugs of alcohols and phenols.

Keywords

Carboxylic Acid Ethyl Ester Olmesartan Medoxomil Losartan Potassium Niflumic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© American Association of Pharmaceutical Scientists 2007

Authors and Affiliations

  • Hans Maag
    • 1
  1. 1.Roche Palo Alto, LLCPalo AltoUSA

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