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P5396 Sigma-Aldrich

Phosphomycin disodium salt

antibacterial MurA inhibitor

Synonym: (−)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid, Fosfomycin, Phosphonomycin

  • CAS Number 26016-99-9

  • Empirical Formula (Hill Notation) C3H5Na2O4P

  • Molecular Weight 182.02

  •  Beilstein/REAXYS Number 4604425

  •  EC Number 247-409-2

  •  MDL number MFCD22741288

  •  PubChem Substance ID 24278640

  •  NACRES NA.85

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Properties

Related Categories Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics N-S, Antibiotics by Mechanism of Action,
Quality Level   200
Mode of action   cell wall synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
storage temp.   2-8°C
SMILES string   [Na+].[Na+].C[C@@H]1O[C@@H]1P([O-])([O-])=O
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
InChI key   QZIQJIKUVJMTDG-JSTPYPERSA-L

Description

Application

Phosphomycin, also known as Fosfomycin, is an antibiotic produced by Streptomyces fradiae. It is used to treat uncomplicated urinary tract infections. It is used for susceptibility studies of Klebsiella pneumoniae and to study in vitro susceptibility testing procedures for fosfomycin tromethamine.

Biochem/physiol Actions

Antibiotic that concentrates in kidney and bladder; reduces nephrotoxicity and ototoxicity of platinum-containing anti-tumor agents. Fosfomycin is a phosphoenolpyruvate analog that irreversibly inhibits UDP-GlcNAc enolpyruvyl tranferase (MurA), an enzyme involved in bacterial cell wall biosynthesis. As a result, the production of N-acetylmuramic acid, an essential element of the peptidoglycan cell wall, is inhibited.

Other Notes

1g,5g,50g

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
SZ7902000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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