Fosfomycin
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Fosfomycin
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| Systematic (IUPAC) name | |
| [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid | |
| Identifiers | |
| CAS number | 78964-85-9 (tromethamine) |
| ATC code | J01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C3H7O4P |
| Mol. mass | 138.059 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 30–37% (oral, fosfomycin tromethamine); varies with food intake |
| Protein binding | Nil |
| Metabolism | Nil |
| Half life | 5.7 hours (mean) |
| Excretion | Renal and fecal, unchanged |
| Therapeutic considerations | |
| Pregnancy cat. |
B(US) |
| Legal status | |
| Routes | Oral |
Fosfomycin (also known as phosphomycin and phosphonomycin) is a broad-spectrum antibiotic produced by certain Streptomyces species.
Fosfomycin is indicated in the treatment of urinary tract infections, where it is usually administered as a single dose. Development of bacterial resistance under therapy is a frequent occurrence and makes fosfomycin unsuitable for sustained therapy of severe infections.
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[edit] Mechanism of action
Fosfomycin is an antimetabolite of phosphoenolpyruvate in the enzymatic synthesis of N-Acetylmuramic acid, 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. Mutations that inactivate this non-essential transport protein render bacteria resistant to fosfomycin.
[edit] 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 research group. Pubmed
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