Welcome to LookChem.com Sign In|Join Free

CAS

  • or

23155-02-4

Post Buying Request

23155-02-4 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

23155-02-4 Usage

Mode of action

The N-acetylmuramic acid component of the bacterial cell wall is derived from N-acetylglucosamine by the addition of a lactic acid substituent derived from phosphoenolpyruvate. Fosfomycin blocks this reaction by inhibiting the pyruvyl transferase enzyme involved. The antibiotic enters bacteria by utilizing active transport mechanisms for α-glycerophosphate and glucose-6-phosphate. Glucose-6-phosphate induces the hexose phosphate transport pathway in some organisms (notably Escherichia coli) and potentiates the activity of fosfomycin against these bacteria.

Chemical Properties

Water-soluble crystals.

Originator

Fosfocin,Crinos,Italy,1977

Uses

Antibacterial.

Definition

ChEBI: A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus.

Manufacturing Process

(A) The preparation of [(1-chloroethoxy)chloromethyl]phosphonic acid: Acetaldehyde (1.1 mol) and hydroxymethylphosphonic acid (1 mol) in 500 ml of benzene are saturated with hydrogen chloride gas at 10°C to 15°C. The mixture is aged at 25°C for 24 hr, the solvent distilled out in vacuo and the residue flushed three times with benzene to remove all traces of hydrogen chloride. The residue is taken up in benzene (500 ml), treated with tert-butyl hypochlorite (0.8 mol) and azobisisobutyronitrile (0.8 mm) at 40°C until titration shows the absence of hypochlorite and the solution is then evaporated to yield [(1-chloroethoxy)chloromethyl] phosphonic acid in the form of an oil. (B) The preparation of (cis-1,2-epoxypropyl)phosphonic acid: [(1- chloroethoxy)chloromethyl] phosphonic acid (1.0 g) is added with stirring to tetrahydrofuran (50 ml) to which has been added a crystal of iodine and a zinc-copper couple (15.0 g). The mixture is then heated under reflux for 24 hr and the resulting solution filtered to yield (cis-1,2-epoxypropyl)-phosphonic acid. There is also a fermentation route to Fosfomycin as noted by Kleeman and Engel.

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.

Metabolism

Fosfomycin undergoes no biotransformation and is excreted mainly unchanged through the kidneys. This results in very high urinary concentrations (up to 3 mg/mL) within 2-4 hours of a dose. Therapeutic concentrations of 200-300 mcg/mL in urine are usually maintained for at least 36 hours, and can last from 48-72 hours.

Check Digit Verification of cas no

The CAS Registry Mumber 23155-02-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,1,5 and 5 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 23155-02:
(7*2)+(6*3)+(5*1)+(4*5)+(3*5)+(2*0)+(1*2)=74
74 % 10 = 4
So 23155-02-4 is a valid CAS Registry Number.
InChI:InChI=1/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1

23155-02-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name fosfomycin

1.2 Other means of identification

Product number -
Other names Fosfomycinum

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:23155-02-4 SDS

23155-02-4Relevant articles and documents

Studies on the biosynthesis of fosfomycin. Conversion of 2-hydroxyethylphosphonic acid and 2-aminoethylphosphonic acid to fosfomycin

Imai,Seto,Ogawa,et al.

, p. 873 - 874 (1985)

-

A new non-chloride method of synthesis of antibacterial antibiotic fosfomycin based on the principles of green chemistry

Belakhov,Garabadzhiu

, p. 2974 - 2977 (2017/07/07)

A new non-chloride method for synthesis of antibacterial antibiotic fosfomycin, which is based on principles of green chemistry, has been developed.

Apparatus And Methods For Delivering A Plurality Of Medicaments For Management Of Co-Morbid Diseases, Illnesses Or Conditions

-

, (2010/09/07)

A method and apparatus for delivering a plurality of medicaments in a single delivery vehicle for the management of co-morbid diseases, illnesses and conditions. The present invention provides a novel delivery process for many medicaments. Medicaments may be encapsulated and stored separately within a larger capsule until the time of ingestion, consumption, or the like. Benefits of the present invention include maintaining separation of distinct ingredients within a single capsule and the capability to control the time release of multiple ingredients within the capsule.

Indirect evidence for the biosynthesis of (1S,2S)-epoxypropylphosphonic acid as a co-metabolite of fosfomycin [(1R,2S)-1,2-epoxypropylphosphonic acid] by Streptomyces fradiae

Simov, Biljana Peric,Wuggenig, Frank,Laemmerhofer, Michael,Lindner, Wolfgang,Zarbl, Elfriede,Hammerschmidt, Friedrich

, p. 1139 - 1142 (2007/10/03)

Treatment of the culture broth of fosfomycin (1) producing Streptomyces fradae with ammonia gives 2-3% of the C-1 epimeric compound 5, as well as the known (1R,2R)-2-amino-1-hydroxypropylphosphonic acid (3) derived from fosfomycin. The configuration of 5 was determined by capillary electrophoresis employing a quinine carbamate-type chiral selector and by synthesis from a monoprotected 1,2-dihydroxypropylphosphonate of known absolute configuration. It is postulated that (1S,2R)-2-amino-1-hydroxypropylphosphonic acid (5) is derived by ring opening of a trans-epoxide, formed as a co-metabolite of fosfomycin (cis-epoxide), with ammonia. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 23155-02-4