Chloramphenicol: Relation of structure to activity and toxicity

A. A. Yunis

Research output: Contribution to journalReview articlepeer-review

83 Scopus citations

Abstract

The availability of an increasing number of effective broad spectrum antimicrobials in the past decade has diminished considerably the clinical indications for chloramphenicol (CAP). However, interest in this antibiotic has recently been revived both because of its antimicrobial activity and its toxicity. Some factors affecting its resurgence are the emergence of ampicillin-resistant Halmophilus influenzae, the superiority of CAP in fighting certain anaerobic infections and infections of the central nervous system, and the development of sensitive assays for the antibiotic and some of its metabolites in body fluids. Greater attention, however, has focused on hematotoxicity from CAP and its pathogenesis. The extensive use of a CAP analogue, thiamphenicol (TAP), in Europe and the Far East, without an increase in the incidence of associated aplastic anemia, has revived interest in the structure-toxicity relationship in the CAP molecule and has focused attention on the p-NO2 group as the structural feature that probably underlies the development of bone marrow aplasia in association with administration of CAP. TAP, with a similar antimicrobial spectrum, has emerged as a challenging substitute to CAP. In this chapter the comparative metabolism and toxicity of CAP and TAP are reviewed with particular emphasis on the role of the p-NO2 group. For a clearer perspective, the properties of CAP, its mechanism of action, and relation of structure to activity and to bacterial resistance are briefly considered.

Original languageEnglish (US)
Pages (from-to)83-100
Number of pages18
JournalAnnual Review of Pharmacology and Toxicology
Volume28
StatePublished - Jan 1 1988

ASJC Scopus subject areas

  • Toxicology
  • Pharmacology

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