Fosfomycin tromethamine Chemical Properties

Melting point:

122-125oC

storage temp. 

Hygroscopic, Refrigerator, under inert atmosphere

solubility 

Very soluble in water, slightly soluble in ethanol (96 per cent) and in methanol, practically insoluble in acetone.

form 

Solid

color 

White to Off-White

Stability:

Hygroscopic

InChI

InChI=1/C4H11NO3.C3H7O4P/c5-4(1-6,2-7)3-8;1-2-3(7-2)8(4,5)6/h6-8H,1-3,5H2;2-3H,1H3,(H2,4,5,6)/t;2-,3+/s3

InChIKey

QZJIMDIBFFHQDW-LMLSDSMGSA-N

SMILES

C(N)(CO)(CO)CO.P([C@H]1O[C@H]1C)(O)(O)=O |&1:9,11,r|

Safety Information

HS Code 

2941906000

Fosfomycin tromethamine Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

Phosphonic acid derivative; antibacterial.

Uses

Fosfomycin Tromethamine is used as an antibiotic compound in the treatment of urinary tract infections.

Definition

ChEBI: Fosfomycin tromethamine is a phosphonoacetic acid.

brand name

Monurol (Zambon).

General Description

Fosfomycin tromethamine (Monurol) is a phosphonic acidepoxide derivative that was initially isolated from fermentationsof Streptomyces spp. Making the tromethamine salt greatly expanded the therapeutic utility of this antibacterial because water solubilityincreased enough to allow oral administration.
Fosfomycin is a broad-spectrum, bactericidal antibacterialthat inhibits the growth of E. coli, S. aureus, andSerratia, Klebsiella, Citrobacter, Enterococcus, andEnterobacter spp. at a concentration less than 64 mg/L.Currently fosfomycin is recommended as single-dose therapyfor uncomplicated urinary tract infections. It possessesin vitro efficacy similar to that of norfloxacin and trimethoprim-sulfamethoxazole.
Fosfomycin covalently inactivates the first enzyme in thebacterial cell wall biosynthesis pathway, UDP-N-acetylglucosamineenolpyruvyl transferase (MurA) by alkylation ofthe cysteine-115 residue. The inactivation reaction occursthrough nucleophilic opening of the epoxide ring. Resistanceto fosfomycin can occur through chromosomal mutationsthat result in reduced uptake or reduced MurA affinity for theinhibitor. Plasmid-mediated resistance mechanisms involveconjugative bioinactivation of the antibiotic with glutathione.The frequency of resistant mutants in in vitro studies hasbeen low, and there appears to be little cross-resistance betweenfosfomycin and other antibacterials.

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