fosfomycin   Click here for help

GtoPdb Ligand ID: 10813

Synonyms: Monurol® | phosphomycin | phosphonomycin | Veramina®
Approved drug PDB Ligand
fosfomycin is an approved drug (UK (1994), FDA (1996))
Compound class: Synthetic organic
Comment: Fosfomycin is a phosphonic acid antibacterial, with broad antibacterial activity against Gram +ve and Gram -ve pathogens [1]. It was originally isolated from certain types of Streptomyces, but it is now made synthetically.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 79.87
Molecular weight 138.01
XLogP -1.58
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES C[C@@H]1O[C@@H]1P(=O)(O)O
Isomeric SMILES C[C@@H]1O[C@@H]1P(=O)(O)O
InChI InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
InChI Key YMDXZJFXQJVXBF-STHAYSLISA-N
No information available.
Summary of Clinical Use Click here for help
Fosfomycin can be used to treat uncomplicated urinary tract infections (UTIs e.g. cystitis) and prostatitis due to susceptible strains of Escherichia coli and Enterococcus faecalis for which it is generally given as a single oral dose as fosfomycin tromethamine. The drug can be administered as intravenous infusion (as the disodium salt), but this parenteral formulation is not available in the US. Fosfomycin is unsuitable for sustained therapy of severe infections as bacterial resistance can develop during therapy. Despite this i.v. fosfomycin (ZTI-01) is being evaluated in clinical studies for treatment of complicated UTIs [2] (NCT02753946). Under EMA jurisdiction, fosfomycin was granted orphan designation (in 2015) in a fixed-dose combination of fosfomycin disodium and tobramycin for the treatment of cystic fibrosis patients.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Fosfomycin inhibits bacterial cell wall biogenesis by inactivating the peptidoglycan biosynthetic enzyme UDP-N-acetylglucosamine-3-enolpyruvyltransferase, (MurA).
External links Click here for help
For extended ADME data see the following:

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