Fosfomycin sodiumProduct ingredient for Fosfomycin

Name
Fosfomycin sodium
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
DBSALT000454
Structure
Synonyms
Fosfomycin disodium / Fosfomycin sodium
UNII
97MMO19FNO
CAS Number
26016-99-9
Weight
Average: 182.0227
Monoisotopic: 181.97208451
Chemical Formula
C3H5Na2O4P
InChI Key
QZIQJIKUVJMTDG-JSTPYPERSA-L
InChI
InChI=1S/C3H7O4P.2Na/c1-2-3(7-2)8(4,5)6;;/h2-3H,1H3,(H2,4,5,6);;/q;2*+1/p-2/t2-,3+;;/m0../s1
IUPAC Name
disodium [(2R,3S)-3-methyloxiran-2-yl]phosphonate
SMILES
[Na+].[Na+].C[C@@H]1O[C@@H]1P([O-])([O-])=O
PubChem Compound
73491
ChemSpider
66181
ChEBI
805124
ChEMBL
CHEMBL1256140
Predicted Properties
PropertyValueSource
Water Solubility51.4 mg/mLALOGPS
logP-0.5ALOGPS
logP-0.74Chemaxon
logS-0.55ALOGPS
pKa (Strongest Acidic)1.25Chemaxon
pKa (Strongest Basic)-4.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area75.72 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity23.63 m3·mol-1Chemaxon
Polarizability10.09 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon