Chemistry and Mechanism of Action
The chemical name of tigecycline is 9-t-butylglycylamido-minocycline and the molecular formula is C29H39N5O8. The addition of the 9-t-butylglycylamido moiety to the minocycline structure at position nine provides tigecycline with the ability to overcome common tetracycline resistance mechanisms in bacteria - ribosomal modification and efflux pumps (Figure 1). As a result, tigecycline displays a broad spectrum of antibacterial activity.[1,2,3,4,5,6]
Tigecycline. Reproduced from .
Similar to tetracycline antibiotics, tigecycline generally exerts bacteriostatic activity through reversible binding to the 30S ribosomal subunits.[1,4,5,6] This mechanism inhibits bacterial protein translation by interrupting amino-acyl tRNA entrance into the A site of the ribosome, which prevents completion of intracellular peptides. In comparison to tetracycline agents, tigecycline binds with a higher affinity to ribosomal target sites, which may account for its greater in vitro activity. Additional data suggest that the increased affinity of tigecycline for the target site may be the result of differences in binding orientation versus other tetracycline agents.
Expert Rev Anti Infect Ther. 2008;6(5):557-567. © 2008 Expert Reviews Ltd.
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Cite this: Establishing the Role of Tigecycline in an era of Antimicrobial Resistance - Medscape - Oct 01, 2008.