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78964-85-9

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78964-85-9 Usage

Chemical Properties

White to off-white powder

Uses

Different sources of media describe the Uses of 78964-85-9 differently. You can refer to the following data:
1. Phosphonic acid derivative; antibacterial.
2. Fosfomycin Tromethamine is used as an antibiotic compound in the treatment of urinary tract infections.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 78964-85-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,8,9,6 and 4 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 78964-85:
(7*7)+(6*8)+(5*9)+(4*6)+(3*4)+(2*8)+(1*5)=199
199 % 10 = 9
So 78964-85-9 is a valid CAS Registry Number.
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+/m.1/s1

78964-85-9 Well-known Company Product Price

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  • Sigma-Aldrich

  • (F0400000)  Fosfomycin trometamol  European Pharmacopoeia (EP) Reference Standard

  • 78964-85-9

  • F0400000

  • 1,880.19CNY

  • Detail
  • USP

  • (1286322)  Fosfomycin tromethamine  United States Pharmacopeia (USP) Reference Standard

  • 78964-85-9

  • 1286322-800MG

  • 4,326.66CNY

  • Detail

78964-85-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name Fosfomycin tromethamine

1.2 Other means of identification

Product number -
Other names FOSFOMYCIN TROMETAMOL

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:78964-85-9 SDS

78964-85-9Synthetic route

fosfomycin bis tromethamine

fosfomycin bis tromethamine

fosfomycin trometamol
78964-85-9

fosfomycin trometamol

Conditions
ConditionsYield
With acetic anhydride In methanol at 20 - 30℃; for 1.33333h;95.1%
fosfomycin bis-tromethamine

fosfomycin bis-tromethamine

fosfomycin trometamol
78964-85-9

fosfomycin trometamol

Conditions
ConditionsYield
Stage #1: fosfomycin bis-tromethamine In methanol at 20℃; for 0.25h;
Stage #2: With Cyclohexyl isocyanate In methanol at 20℃; for 0.633333h; Reagent/catalyst;
90.5%
(1R,2S)-(-)-cis-1,2-epoxypropyl phosphoric acid-R-(+)-α-phenethylamine salt

(1R,2S)-(-)-cis-1,2-epoxypropyl phosphoric acid-R-(+)-α-phenethylamine salt

2-amino-2-hydroxymethyl-1,3-propanediol
77-86-1

2-amino-2-hydroxymethyl-1,3-propanediol

fosfomycin trometamol
78964-85-9

fosfomycin trometamol

Conditions
ConditionsYield
Stage #1: (1R,2S)-(-)-cis-1,2-epoxypropyl phosphoric acid-R-(+)-α-phenethylamine salt; 2-amino-2-hydroxymethyl-1,3-propanediol In methanol at 20℃; for 0.25h;
Stage #2: With Cyclohexyl isocyanate In methanol at 20 - 33℃; for 0.633333h; Reagent/catalyst;
86.2%
C3H7O4P*C8H11N*C4H11NO3

C3H7O4P*C8H11N*C4H11NO3

fosfomycin trometamol
78964-85-9

fosfomycin trometamol

Conditions
ConditionsYield
With methanesulfonic acid In ethanol at 48 - 50℃; for 0.833333h; Reagent/catalyst; Temperature;72.3%
With methanesulfonic acid In ethanol at 48 - 50℃; for 0.833333h; Temperature;
2-amino-2-hydroxymethyl-propane-1,3-diol; hydrogenoxalate
855392-18-6

2-amino-2-hydroxymethyl-propane-1,3-diol; hydrogenoxalate

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

fosfomycin trometamol
78964-85-9

fosfomycin trometamol

Conditions
ConditionsYield
In methanol at 20 - 65℃; for 3 - 4h;

78964-85-9Downstream Products

78964-85-9Relevant articles and documents

Preparing method of fosfomycin trometamol

-

Paragraph 0025; 0026; 0027, (2019/04/26)

The invention belongs to the technical field of medicinal chemistry, and particularly relates to a preparing method of fosfomycin trometamol. The method includes the following steps of firstly, addingfosfomycin diaminoglycol to methyl alcohol, dropwise adding acetic anhydride or propionic anhydride at a room temperature, and removing the methyl alcohol after a stirring reaction to obtain white solid; secondly, adding absolute ethyl alcohol to the obtained white solid, conducting cooling and filtering, conducting washing with ethyl alcohol, and conducting vacuum drying to obtain the fosfomycintrometamol. According to the preparing method, the acetic anhydride which is low in price and low in toxicity is adopted as the raw material, cost is low, three wastes are few, the environment protection pressure is small, the yield is high, operation is simple and convenient, and the method is suitable for industrial production; in the preparing method, no low-temperature ion exchange column isneeded, the fosfomycin diaminoglycol and acetic anhydride react at a room temperature, the reaction conditions are mild, and energy consumption is low.

Method for conveniently preparing fosfomycin trometamol

-

Paragraph 0038; 0039; 0040; 0041; 0042; 0043; 0044-0077, (2019/01/08)

The invention discloses a synthesis method of fosfomycin trometamol. The method comprises the following steps: (1), taking fosfomycin phenylethylamine salt and tromethamine as raw material to preparefosfomycin bis (alpha-methylbenzylamine/tromethamine) salt, adding an alcoholic solution of methanesulfonic acid or para-toluenesulfonic acid in a stirring condition, stirring and performing cooling crystallization after dropwise adding is accomplished, and filtering to obtain a crude wet product; and (2), refining the crude product to obtain a refined product, and performing vacuum drying, so asto obtain a refined dried product. The method is simple to operate and mild in reaction condition, and ensures that both the product purity and the yield achieve high levels.

A process for the preparation of fosfomycin salts

-

Page/Page column 2, (2008/06/13)

A process for the preparation of fosfomycin trometamol, which comprises the reaction between fosfomycin disodium salt and a tromethamine acid salt with a carboxylic acid in a substantially anhydrous alcoholic solvent.

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