Fosfomycin calcium monohydrateProduct ingredient for Fosfomycin

Name
Fosfomycin calcium monohydrate
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
DBSALT000780
Structure
Synonyms
Not Available
UNII
T330QG2NYS
CAS Number
26469-67-0
Weight
Average: 196.152
Monoisotopic: 195.981351065
Chemical Formula
C3H9CaO5P
InChI Key
MSHCINMVQZDXTG-JSTPYPERSA-N
InChI
InChI=1S/C3H7O4P.Ca.H2O/c1-2-3(7-2)8(4,5)6;;/h2-3H,1H3,(H2,4,5,6);;1H2/q;+2;/t2-,3+;;/m0../s1
IUPAC Name
calcium [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid hydrate
SMILES
O.[Ca++].[H][C@@]1(C)O[C@]1([H])P(O)(O)=O
PubChem Compound
20846144
ChemSpider
20163139
Predicted Properties
PropertyValueSource
Water Solubility46.9 mg/mLALOGPS
logP-0.86ALOGPS
logP-0.74Chemaxon
logS-0.47ALOGPS
pKa (Strongest Acidic)1.25Chemaxon
pKa (Strongest Basic)-4.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area70.06 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity25.87 m3·mol-1Chemaxon
Polarizability10.61 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon