Françoise Van Bambeke

Josamycin and Rosaramicin

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

VO·LUME 1, pages 819-824

2010 Edward Arnold (Publishers) Ltd,

Josamycin and rosaramlcm (rosamicin, rosamycin), together with
spiramycin (see Chapter 182, Spiramycin), share the property of being
constructed on a 16,atom macro cycle instead of a 14,atom macrocycle
as most macrolides, or a 15,atom macro cycle as in azithromycin.
Within this class, a series of molecules have been assessed clinically,
with often only limited success. These include natural products,
including spiramycin (isolated from Streptomyces ambofaciens (Kellow
et al., 1955)), josamycin (isolated from S. narbonensis var. josamyceticus
(Nitta et al., 1967)), rosaramicin, formerly called rosamicin (isolated
from Micromonospora rosaria (Wagman et al., 1972j Waitz et al., 1972)),
midecamycin (Kanazawa and Kuramata, 1976), and semisynthetic
compounds such as miocamycin, derived from midecamycin (Omoto
et al., 1976j Kawaharajo et al., 1981), and rokitamycin, derived from
leucomycin AS (Sakakibara et al., 1981).

This chapter is limited to the description of josamycin (CAS number
16846,24,5j molecular formula C42H69N015j molecular weight
828.00), and rosaramicin (CAS number 35834,26,5j molecular
formula C31H51N09j molecular weight 581.74). The chemical
structures of these two agents are shown in Figure 63.1. Their
spectrum of activity is similar to that of other macrolides.