Hydrolysis of Drugs

Authored by: Jason M. LePree , Kenneth A. Connors

Encyclopedia of Pharmaceutical Science and Technology

Print publication date:  July  2013
Online publication date:  July  2013

Print ISBN: 9781841848198
eBook ISBN: 9781351124874
Adobe ISBN:

10.1081/E-EPT4-v3-25

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Abstract

The term “hydrolysis” describes a chemical reaction in which a chemical bond is split (lysis) through the addition of water. This reaction is one of the more important routes of drug decomposition because it occurs frequently in active ingredients and excipients of pharmaceutical dosage forms. A search of the scientific literature performed with a popular electronic database and using the combination of keywords “hydrolysis” and “drugs” yielded over 109,000 articles that were published between 1999 and 2011. A more selective analysis of a collection of stability data on 91 pharmaceuticals (1) shows that 70 of these undergo hydrolytic degradation reactions. Of these, 61% can be classified as reactions of carboxylic acid derivatives, 4.3% of phosphoric acid derivatives, 20% of carbonyl derivatives, and 14.3% are nucleophilic displacements, often on the aliphatic carbon. These classes are discussed in the subsequent sections of this chapter. Kinetic phenomena for study, including catalysis, temperature dependence, solvent effects, and pressure effects on hydrolysis reaction rates, have been reviewed in the first edition of this encyclopedia (2), and elsewhere (3,4), and will not be discussed in this edition.

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