Fosfomycin

Base Information

• Chemical Name: Fosfomycin
• CAS No.: 23155-02-4
• Molecular Formula: C3H7O4P
• Molecular Weight: 138.06
• Hs Code.: 2931900090
• European Community (EC) Number: 245-463-1
• UNII: 2N81MY12TE
• DSSTox Substance ID: DTXSID4048480
• Nikkaji Number: J34.117G
• Wikipedia: Fosfomycin
• Wikidata: Q183554
• NCI Thesaurus Code: C61772
• RXCUI: 4550
• Metabolomics Workbench ID: 43116
• ChEMBL ID: CHEMBL1757
• Mol file: 23155-02-4.mol

Synonyms:Phosphonicacid, (1,2-epoxypropyl)-, (1R,2S)-(-)- (8CI);Phosphonic acid, (3-methyloxiranyl)-,(2R-cis)-;Phosphonic acid, [(2R,3S)-3-methyloxiranyl]- (9CI);(-)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid;(-)-(cis-1,2-Epoxypropyl)phosphonic acid;(-)-Phosphonomycin;(2R-cis)-(3-Methyloxiranyl)phosphonic acid;Antibiotic 833A;Fosfocina;Fosfomicin;Fosfonomycin;Infectophos;Levo-phosphonomycin;MK0955;Phosphomycin;Phosphonomycin;[(2R,3S)-3-Methyloxiranyl]phosphonic acid;

Chemical Property of Fosfomycin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 94 °C
• Refractive Index: 1.486
• Boiling Point: 342.651 °C at 760 mmHg
• PKA: 3.20±0.40(Predicted)
• Flash Point: 161.03 °C
• PSA: 79.87000
• Density: 1.561 g/cm³
• LogP: -0.09110
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 138.00819570
• Heavy Atom Count: 8
• Complexity: 138

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiinfective Agents
• Canonical SMILES: CC1C(O1)P(=O)(O)O
• Isomeric SMILES: C[C@H]1[C@H](O1)P(=O)(O)O
• Recent ClinicalTrials: Single Dose Monurol for Treatment of Acute Cystitis
• Recent EU Clinical Trials: A double-blind, randomised, multi-centre, controlled clinical trial to compare D-mannose versus antibiotic in the treatment of acute uncomplicated lower urinary tract infections in female patients
• Recent NIPH Clinical Trials: A trial of a combination therapy of fecal microbial transplantation and antibiotics for inflammatory bowel disease
• Uses: Antibacterial.
• Therapeutic Function: Antibiotic
• Clinical Use: Phosphomycin, introduced in 1972, inhibits enolpyruvial transferase, an enzyme catalyzing an early step in bacterial cell wall biosynthesis. Inhibition results in reduced synthesis of peptidoglycan, an important component in the bacterial cell wall. Phosphomycin is bactericidal against Escherichi a coli and Enterobacter faecali s infections.
• Drug interactions: Potentially hazardous interactions with other drugs Metoclopramide: increases gastrointestinal motility and therefore lowers the serum concentration and urinary excretion of fosfomycin.

Technology Process of Fosfomycin

There total 7 articles about Fosfomycin 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:

(S)-2-hydroxypropylphosphonic acid → fosfomycin (23155-02-4)

Guidance literature:

With Streptomyces fradiae;

Reference yield:

phosphomycin disodium salt (26016-99-9) → fosfomycin (23155-02-4)

Guidance literature:

With Dowex 50x8, H(+); In water;

DOI:10.1039/b821829c

Reference yield:

(2-aminethyl)phosphonic acid (2041-14-7) → fosfomycin (23155-02-4)

Guidance literature:

In water; at 28 ℃; for 120h; blocked mutant of Streptomyces wedmorensis ATCC 21239, pH 8.0;

DOI:10.1271/bbb1961.49.873

upstream raw materials:

(2-aminethyl)phosphonic acid

β-Hydroxyethanphosphonsaeure

phosphomycin disodium salt

1,2-propenephosphonic acid

Downstream raw materials:

tobramycin

Benzoic acid (1R,2R)-2-benzoylamino-1-(dimethoxy-phosphoryl)-propyl ester

Refernces

• 1、 Zhao, Zongbao,Liu, Pinghua,Murakami, Kazuo,Kuzuyama, Tomohisa,Seto, Haruo,Liu, Hung-wen. "Mechanistic studies of HPP epoxidase: Configuration of the substrate governs its enzymatic fate". . p. 4529 - 4532. Retrieved 2002.
• 2、 Huang, Hui,Chang, Wei-Chen,Romo, Anthony,Mansoorabadi, Steven O.,Liu, Hung-Wen,Pai, Pei-Jing,Russell, David H.. "Evidence for radical-mediated catalysis by HppE: A study using cyclopropyl and methylenecyclopropyl substrate analogues". supporting information. p. 16171 - 16174,4. Retrieved 2020/09/09.
• 3、 McGrath, John W.,Hammerschmidt, Friedrich,Preusser, Werner,Quinn, John P.,Schweifer, Anna. "Studies on the biodegradation of fosfomycin: Growth of Rhizobium huakuii PMY1 on possible intermediates synthesised chemically". experimental part. p. 1944 - 1953. Retrieved 2009/06/28.