Chemical Component Summary

NameFOSFOMYCIN
Synonyms1,2-EPOXYPROPYLPHOSPHONIC ACID
Identifiers[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
FormulaC3 H7 O4 P
Molecular Weight138.059
TypeNON-POLYMER
Isomeric SMILESC[C@H]1[C@H](O1)P(=O)(O)O
InChIInChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
InChIKeyYMDXZJFXQJVXBF-STHAYSLISA-N

Chemical Details

Formal Charge0
Atom Count15
Chiral Atom Count2
Bond Count15
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB00828 
NameFosfomycin
Groups approved
DescriptionFosfomycin was discovered in 1969 by scientists at the Spanish Penicillin and Antibiotics Company and is produced by _Streptomyces fradiae_.[A229338,A230348] 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.[A230348] In terms of chemical structure, fosfomycin is a phosphoenolpyruvate analog and contains a phosphonic group and an epoxide ring.[A230348] 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.[A230378] 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.[A230348] As such there is great interest in exploring the usefulness of fosfomycin for indications beyond the treatment of UTIs.[A230353,A230358]
Synonyms
  • Fosfomycine
  • Fosfomycin sodium
  • (2R-cis)-(3-Methyloxiranyl)phosphonic acid
  • cis-(1R,2S)-epoxypropylphosphonic acid
  • Phosphonomycin
Brand Names
  • Jamp-fosfomycin
  • Fosfomycin Powder for Oral Solution
  • Fosfomycin Tromethamine
  • Ivozfo
  • Monurol
IndicationFosfomycin is indicated for the treatment of uncomplicated cases of cystitis caused by susceptible strains of _Escherichia coli_ and _Enterococcus faecalis_.[L31818] Fosfomycin is not officially indicated for the treatment of pyelonephritis or perinephric abscess, although there have been reported cases of off-label usage in these situations.[L31818]
Categories
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Anti-Infective Agents, Urinary
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-Code
  • S02AA17
  • J01XX01
CAS number23155-02-4

Drug Targets

NameTarget SequencePharmacological ActionActions
UDP-N-acetylglucosamine 1-carboxyvinyltransferaseMDKFRVQGPTKLQGEVTISGAKNAALPILFAALLAEEPVEIQNVPKLKDV...unknowninhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 446987
ChEMBL CHEMBL1757
ChEBI CHEBI:28915