Streptomycin and other antibiotics that are close analogs (Fig. 6.1) all contain a streptamine aminocyclitol, which is linked to a streptose ring, which in turn is linked to an N-methylglucosamine. Of the 10 natural streptomycin-like compounds listed in Fig. 6.1, all have guanidino groups at the Cl and C3 position except for bluensomycin, which contains a carbamoyl group at the Cl position instead. Some variation is tolerated within the streptose ring: the aldehyde can be reduced to an alcohol, and methyl alcohol can substitute for the methyl at the C4' position (34). Considerable modifications of the glucosamine moiety are also tolerated.
Shortly after its discovery, streptomycin was brought into service to treat Gram-negative and some Gram-positive infections, with its greatest contribution coming as the primary agent to treat tuberculosis (35). Its use has waned over the years because bacterial resistance against streptomycin has emerged and less toxic agents have become available. Nonetheless, it is still frequently used as a component of a multi-drug mixture to treat multi-drug resistant cases of tuberculosis.
Was this article helpful?