Fosfomycin tromethamineProduct ingredient for Fosfomycin
- Name
- Fosfomycin tromethamine
- Drug Entry
- Fosfomycin
Fosfomycin was discovered in 1969 by scientists at the Spanish Penicillin and Antibiotics Company and is produced by Streptomyces fradiae.1,5 It may also be produced synthetically and is commercially available as the disodium salt for intravenous administration and as the calcium or trometamol salt for oral administration.5 In terms of chemical structure, fosfomycin is a phosphoenolpyruvate analog and contains a phosphonic group and an epoxide ring.5
Due to its ease of administration as a single 3-gram oral dose and desirable safety profile, fosfomycin has largely become a first-line therapeutic option for the treatment of uncomplicated urinary tract infections (UTIs) in females.8 Despite being FDA approved only for urinary tract infections, fosfomycin actually has a broad spectrum of activity and is active against both gram-positive and gram-negative bacteria.5 As such there is great interest in exploring the usefulness of fosfomycin for indications beyond the treatment of UTIs.6,7
- Accession Number
- DBSALT000781
- Structure
Structure for Fosfomycin tromethamine (DBSALT000781)
- Synonyms
- Fosfomycin tromethamine / Fosfomycin tromethanol
- External IDs
- Z 1282
- UNII
- 7FXW6U30GY
- CAS Number
- 78964-85-9
- Weight
- Average: 259.1941
Monoisotopic: 259.082088447 - Chemical Formula
- C7H18NO7P
- InChI Key
- QZJIMDIBFFHQDW-LMLSDSMGSA-N
- InChI
- InChI=1S/C4H11NO3.C3H7O4P/c5-4(1-6,2-7)3-8;1-2-3(7-2)8(4,5)6/h6-8H,1-3,5H2;2-3H,1H3,(H2,4,5,6)/t;2-,3+/m.0/s1
- IUPAC Name
- 2-amino-2-(hydroxymethyl)propane-1,3-diol; [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
- SMILES
- C[C@@H]1O[C@@H]1P(O)(O)=O.NC(CO)(CO)CO
- External Links
- KEGG Drug
- D00925
- PubChem Compound
- 54331
- ChemSpider
- 49075
- ChEBI
- 5162
- ChEMBL
- CHEMBL1200331
- Wikipedia
- Fosfomycin
- Predicted Properties
Property Value Source logP -0.74 Chemaxon pKa (Strongest Acidic) 1.25 Chemaxon pKa (Strongest Basic) -4.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 66.76 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 25.87 m3·mol-1 Chemaxon Polarizability 10.8 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon