FCN

FOSFOMYCIN

Created:1999-07-08
Last modified:  2021-03-13

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Chemical Details

Formal Charge0
Atom Count15
Chiral Atom Count2
Bond Count15
Aromatic Bond Count0
2D diagram of FCN
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Chemical Component Summary

NameFOSFOMYCIN
Synonyms1,2-EPOXYPROPYLPHOSPHONIC ACID
Systematic Name (OpenEye OEToolkits)[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
FormulaC3 H7 O4 P
Molecular Weight138.059
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04O=P(O)(O)C1OC1C
SMILESCACTVS3.341C[CH]1O[CH]1[P](O)(O)=O
SMILESOpenEye OEToolkits1.5.0CC1C(O1)P(=O)(O)O
Canonical SMILESCACTVS3.341 C[C@@H]1O[C@@H]1[P](O)(O)=O
Canonical SMILESOpenEye OEToolkits1.5.0 C[C@H]1[C@H](O1)P(=O)(O)O
InChIInChI1.03 InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
InChIKeyInChI1.03 YMDXZJFXQJVXBF-STHAYSLISA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB00828 
NameFosfomycin
Groups
  • approved
  • investigational
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
  • cis-(1R,2S)-epoxypropylphosphonic acid
  • Phosphomycin
  • L-cis-1,2-epoxypropylphosphonic acid
  • 1R-cis-(1,2-epoxypropyl)phosphonic acid
  • Fosfomycin tromethamine
Brand Names
  • Monurol
  • Fosfomycin tromethamine
  • Jamp-fosfomycin
  • Ivozfo
  • Fosfomycin Powder for Oral Solution
IndicationFosfomycin is indicated for the treatment of uncomplicated urinary tract infections (acute cystitis) in women due to susceptible strains of _Escherichia coli_ and _Enterococcus faecalis_.[L31818] It is also indicated to treat adults with complicated urinary tract infections (cUTI), including acute pyelonephritis, caused by susceptible isolates of _Escherichia coli_ and _Klebsiella pneumoniae_.[L54511]
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

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
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