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P5396

Sigma-Aldrich

Phosphomycin disodium salt

antibacterial MurA inhibitor

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C3H5Na2O4P
Poids moléculaire :
182.02
Numéro Beilstein :
4604425
Numéro CE :
247-409-2
Numéro MDL:
MFCD22741288
Code UNSPSC :
51102829
ID de substance PubChem :
24278640
Nomenclature NACRES :
NA.85

Niveau de qualité

200

Forme

powder

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria

Mode d’action

cell wall synthesis | interferes

Température de stockage

2-8°C

Chaîne SMILES 

[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

Clé InChI

QZIQJIKUVJMTDG-JSTPYPERSA-L

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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.

Actions biochimiques/physiologiques

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.

Autres remarques

1g,5g,50g
Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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A L Barry et al.
Antimicrobial agents and chemotherapy, 35(6), 1235-1238 (1991-06-01)
Fosfomycin tromethamine (previously fosfomycin trometamol) is an orally administered fosfomycin which may be used for single-dose therapy of uncomplicated urinary tract infections. Fosfomycin tromethamine, norfloxacin, and trimethoprim-sulfamethoxazole inhibited greater than 90% of 352 bacterial isolates representing 25 different species; trimethoprim
Andrea Endimiani et al.
Antimicrobial agents and chemotherapy, 54(1), 526-529 (2009-11-11)
In vitro activity of fosfomycin was evaluated against 68 bla(KPC)-possessing Klebsiella pneumoniae (KpKPC) isolates, including 23 tigecycline- and/or colistin-nonsusceptible strains. By agar dilution, 93% of the overall KpKPC were susceptible (MIC(50/90) of 16/64 microg/ml, respectively). The subgroup of 23 tigecycline-
Avigail Stokar-Avihail et al.
Cell host & microbe, 25(5), 746-755 (2019-05-10)
Temperate phages can adopt either a lytic or lysogenic lifestyle within their host bacteria. It was recently shown that Bacillus-subtilis-infecting phages of the SPbeta group utilize a peptide-based communication system called arbitrium to coordinate the lysogeny decision. The occurrence of peptide-based
Nikos Fatsis-Kavalopoulos et al.
PLoS biology, 18(9), e3000856-e3000856 (2020-09-18)
Antibiotic combination therapies are important for the efficient treatment of many types of infections, including those caused by antibiotic-resistant pathogens. Combination treatment strategies are typically used under the assumption that synergies are conserved across species and strains, even though recent

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