medicine: monurol

monurol description








Fosfomycin (also known as phosphomycin and phosphonomycin) is a broad-spectrum antibiotic produced by certain Streptomyces species.

Uses

Fosfomycin is indicated in the treatment of urinary tract infections, where it is usually administered as a single oral megadose.

The drug is well tolerated and has a low incidence of harmful side-effects. However, development of bacterial resistance under therapy is a frequent occurrence and makes fosfomycin unsuitable for sustained therapy of severe infections.

Additional uses have been proposed. The global problem of advancing antimicrobial resistance has led to a renewed interest in its use more recently.

Mechanism of action

Fosfomycin is an antimetabolite of phosphoenolpyruvate in the enzymatic synthesis of N-acetylmuramic acid via enolpyruvate transferase, a component of the bacterial cell wall glycopeptide murein. The epoxide ring of fosfomycin covalently reacts with a cysteine residue in the enzyme's active site, which results in the enzyme's irreversible inactivation.

Fosfomycin enters the bacterial cell through the glycerophosphate transporter.

Resistance

Mutations that inactivate the non-essential glycerophosphate transporter render bacteria resistant to fosfomycin. Three groups of fosfomycin resistance enzymes have also been identified: FosA, FosB and FosX. FosA adds a glutathione molecule to fosfomycin, whereas FosB and FosX add cysteine or water, respectively, to fosfomycin. All three enzymes attack carbon 1 of fosfomycin, which opens the epoxide ring and renders the drug ineffective.

Biosynthetic gene cluster

The complete fosfomycin biosynthetic gene cluster from Streptomyces fradiae has been cloned and sequenced and the heterologous production of fosfomycin in Streptomyces lividans has been achieved by Ryan Woodyer of the Huimin Zhao and Wilfred van der Donk research groups.

See also

fosmidomycin

Tags

Keywords related to monurol

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