Disodium phosphonomycin

Base Information

• Chemical Name: Disodium phosphonomycin
• CAS No.: 26016-99-9
• Molecular Formula: C3H5Na2O4P
• Molecular Weight: 182.024
• Hs Code.: 29419090
• European Community (EC) Number: 247-409-2
• ChEMBL ID: CHEMBL1520976
• Mol file: 26016-99-9.mol

Synonyms:Phosphomycin disodium;Fosfomycin sodium;Disodium phosphonomycin;26016-99-9;Fosfomycin disodium salt;C3H5O4P.2Na;C3H7O4P.2Na;C3-H5-O4-P.2Na;CHEMBL1520976;Phosphonic acid, (1,2-epoxypropyl)-, disodium salt, (1R,2S)-(-)-;HMS3262P20;25162-71-4;BCP11834;Tox21_500959;Fosfomycin;Phosphonomycin;MK-955;AKOS040759350;CCG-222263;LP00959;NCGC00016194-02;NCGC00094260-01;NCGC00261644-01;Sodium (3-methyloxiran-2-yl)phosphonate;disodium (3-methyloxiran-2-yl)phosphonate;CS-0283072;EU-0100959;EN300-296114;P 5396;A818139;disodium (3-methyloxiran-2-yl)-dioxido-oxo-$l^{5}-phosphane;Fosfomycin Disodium Salt;Phosphomycin disodium salt;(-)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid disodium salt

Chemical Property of Disodium phosphonomycin

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1.34E-05mmHg at 25°C
• Melting Point: >300 °C
• Boiling Point: 342.7oC at 760 mmHg
• Flash Point: 161°C
• PSA: 85.53000
• LogP: 0.78530
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL, clear, colorless
• Water Solubility.: Freely soluble in water or aqueous solution
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 181.97208420
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

99% ^*data from raw suppliers

Fosfomycin Disodium Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C
• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 16-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(O1)P(=O)([O-])[O-].[Na+].[Na+]
• Recent EU Clinical Trials: Pharmacokinetics of a novel extended infusion regimen of fosfomycin
• Indications: Mainly used for Staphylococcus aureus, streptococcus, E. coli, Salmonella and other gram-negative bacteria caused acute and chronic bowel disease treatment in chickens, ducks, pigs.
• Uses: For the treatment of infections caused by Staphylococcus aureus, Escherichia coli, Proteus and Shigella. Curariform muscle relaxants Disodium phosphonomycin, also known as Fosfomycin, is an antibiotic produced by Streptomyces fradiae. It is used to treat uncomplicated urinary tract infections and to reduce nephrotoxicity and ototoxicity of platinum-containing anti-tumor agents. It is used for susceptibility studies of Klebsiella pneumoniae and to study in vitro susceptibility testing procedures for fosfomycin tromethamine Prevents peptidoglycan synthesis by inhibiting MurA, an enzyme responsible for synthesizing N-acetylmuramic acid or NAM, a major component of peptidoglycan

Technology Process of Disodium phosphonomycin

There total 6 articles about Disodium phosphonomycin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

syn-(1R,2S)-1-chloro-2-hydroxypropane phosphonic acid disodium salt → phosphomycin disodium salt (26016-99-9)

Guidance literature:

With sodium hydroxide; for 1h;

DOI:10.1016/j.tetasy.2011.10.009

Reference yield: 76.0%

dibenzyl (1R,2S)-1,2-epoxypropylphosphonate (172585-28-3) → phosphomycin disodium salt (26016-99-9)

Guidance literature:

With Dowex 50WX₈ (Na form); hydrogen; cyclohexylamine; palladium on activated charcoal; In methanol;

DOI:10.1016/0957-4166(95)00281-S

Reference yield:

disodium (1S,2S)-2-hydroxy-1-methanesulphonyloxypropyl phosphonate → phosphomycin disodium salt (26016-99-9)

Guidance literature:

With sodium hydroxide; In water;

upstream raw materials:

(1-bromo-2-hydroxypropyl)phosphonic acid

dibenzyl (1R,2S)-1,2-epoxypropylphosphonate

(1R,2S)-1-chloro-2-hydroxypropanephosphonic acid

Downstream raw materials:

fosfomycin

fosfomycin trometamol

((1R,2R)-1,2-Dihydroxy-propyl)-phosphonic acid; compound with cyclohexylamine

Refernces

• 1、 Wang, Ke,Zhang, Yonghui,Yuan, Chengye. "Enzymatic synthesis of phosphocarnitine, phosphogabob and fosfomycin". . p. 3564 - 3569. Retrieved 2003.
• 2、 -. "Process for the preparation of intermediates for the synthesis of fosfomycin". . . Retrieved 2008/06/13.