Claire Gordon, Françoise Van Bambeke

Azithromycin

In: KUCERS' THE USE OF ANTIBIOTICS: A CLINICAL REVIEW OF ANTIBACTERIAL,
ANTIFUNGAL, ANTIPARASITIC AND ANTIVIRAL DRUGS
6TH EDITION

VOLUME 1, pages 801-818

2010 Edward Arnold (Publishers) Ltd,

Azithromycin (CAS number: 83905-01-5) was obtained by Beckman
rearrangement of the oxime derivative of the ketone of erythromycin
(see Chapter 59, Erythromycin), leading to a IS-membered macrocycle,
followed by its reduction and N-alkylation (hence the name
of azalide given to this class of compounds (Dfokic et al., 1987; Bright
et al.,_1988). The molecular formula is C3sHnNz012 and the
molecular weight is 749; the structure is shown in Figure 62.1.
Azithromycin has greater in vitro activity than erythromycin against
some Gram-negative bacteria and improved pharmacokinetics with a
relatively long half-life (Dunkin et al., 1988; Maskell et al., 1990). It
accumulates significantly intracellularly. It also shows activity against
nontuberculous mycobacteria, including Mycobacterium avium complex
(MAC) (Watt et al., 1996a), and some parasites, such as Toxoplasma
gondii (Araujo et al., 1988).

Apart from its use as an antimicrobial
agent, it is increasingly used as an anti-inflammatory agent, in
particular in patients with cystic fibrosis.