| Accession | ARO:0000025 |
| Synonym(s) | (1R,2S)-1,2-epoxy-propylphosphonic acid phosphomycin phosphonomycin |
| Definition | Fosfomycin (also known as phosphomycin and phosphonomycin) is a broad-spectrum antibiotic produced by certain Streptomyces species. It is effective on gram positive and negative bacteria as it targets the cell wall, an essential feature shared by both bacteria. Its specific target is MurA (MurZ in E.coli), which attaches phosphoenolpyruvate (PEP) to UDP-N-acetylglucosamine, a step of commitment to cell wall synthesis. In the active site of MurA, the active cysteine molecule is alkylated which stops the catalytic reaction. |
| SMILES | N/A |
| PubChem | 73491 |
| Drug Class | phosphonic acid antibiotic |
| Classification | 2 ontology terms | Show |
| Parent Term(s) | 1 ontology terms | Show + phosphonic acid antibiotic [Drug Class] |
| Sub-Term(s) | 49 ontology terms | Show + FomA confers_resistance_to_antibiotic + FomB confers_resistance_to_antibiotic + FosC confers_resistance_to_antibiotic + FosA confers_resistance_to_antibiotic + FosB confers_resistance_to_antibiotic + FosX confers_resistance_to_antibiotic + Escherichia coli GlpT with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic + Escherichia coli UhpT with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic + Escherichia coli uhpA with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic + Escherichia coli PtsI with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic + Escherichia coli cyaA with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic + Staphylococcus aureus GlpT with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic + Staphylococcus aureus UhpT with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic + Staphylococcus aureus FosB confers_resistance_to_antibiotic + FosA6 confers_resistance_to_antibiotic + FosA7 confers_resistance_to_antibiotic + mdtG confers_resistance_to_antibiotic + FosY confers_resistance_to_antibiotic + FosM1 confers_resistance_to_antibiotic + FosM2 confers_resistance_to_antibiotic + FosM3 confers_resistance_to_antibiotic + Acinetobacter baumannii AbaF confers_resistance_to_antibiotic + FosG confers_resistance_to_antibiotic + FosH confers_resistance_to_antibiotic + FosI confers_resistance_to_antibiotic + FosA8 confers_resistance_to_antibiotic + FosBx1 confers_resistance_to_antibiotic + FosA2 confers_resistance_to_antibiotic + FosA3 confers_resistance_to_antibiotic + FosA4 confers_resistance_to_antibiotic + FosA7.5 confers_resistance_to_antibiotic + FosB1 confers_resistance_to_antibiotic + FosB2 confers_resistance_to_antibiotic + FosB3 confers_resistance_to_antibiotic + FosB4 confers_resistance_to_antibiotic + FosB5 confers_resistance_to_antibiotic + FosB6 confers_resistance_to_antibiotic + FosC2 confers_resistance_to_antibiotic + FosD confers_resistance_to_antibiotic + FosK confers_resistance_to_antibiotic + FosL1 confers_resistance_to_antibiotic + FosXCC confers_resistance_to_antibiotic + Borreliella burgdorferi murA with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic + Chlamydia trachomatis intrinsic murA conferring resistance to fosfomycin confers_resistance_to_antibiotic + Escherichia coli murA with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic + Mycobacterium tuberculosis intrinsic murA conferring resistance to fosfomycin confers_resistance_to_antibiotic + Staphylococcus aureus murA with mutation conferring resistance to fosfomycin confers_resistance_to_antibiotic + msr(I) confers_resistance_to_antibiotic + fosfomycin sensitive pyruvyl transferase (murA) targeted_by_antibiotic |
| Publications | Fillgrove KL, et al. 2007. Biochemistry 46(27): 8110-8120. Structure and mechanism of the genomically encoded fosfomycin resistance protein, FosX, from Listeria monocytogenes. (PMID 17567049) Hendlin D, et al. 1969. Science 166(901): 122-123. Phosphonomycin, a new antibiotic produced by strains of streptomyces. (PMID 5809587) Brown ED, et al. 1994. Biochemistry 33(35): 10638-10645. Detection and characterization of a phospholactoyl-enzyme adduct in the reaction catalyzed by UDP-N-acetylglucosamine enolpyruvoyl transferase, MurZ. (PMID 8075064) Skarzynski T, et al. 1996. Structure 4(12): 1465-1474. Structure of UDP-N-acetylglucosamine enolpyruvyl transferase, an enzyme essential for the synthesis of bacterial peptidoglycan, complexed with substrate UDP-N-acetylglucosamine and the drug fosfomycin. (PMID 8994972) Pakhomova S, et al. 2008. J Biol Chem 283(42): 28518-28526. Crystal structure of fosfomycin resistance kinase FomA from Streptomyces wedmorensis. (PMID 18701452) |
| Curator | Description | Most Recent Edit |
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