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26016-99-9

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26016-99-9 Usage

Appearance Properties

It appears as a white crystalline powder at room temperature, hygroscopic, easily soluble in water, heated while dissolving. Fosfomycin Sodium can combine with a bacterial cell wall synthesis enzyme, hinder bacterial cell wall synthesis related substances utilizing at the first reaction, which in turn has a bactericidal effect. have antibacterial effect for Staphylococcus aureus, Streptococcus pneumoniae, Escherichia coli, Neisseria gonorrhoeae, Proteus mirabilis, Salmonella typhi, Serratia bacteria, most Pseudomonas aeruginosa, Streptococcus pyogenes, Streptococcus faecalis, part indole-positive Proteus and certain Klebsiella, Enterobacter bacteria. The main clinical applications of Fosfomycin Sodium include: urinary tract treatment of sensitive Gram-negative bacteria caused urinary system, infection of skin and soft tissue, respiratory, intestinal and other parts. It can also be combined with other antibiotics, the treatment of severe infections caused by susceptible strains such as sepsis, pulmonary, meningeal infections, peritonitis, adnexitis, intrauterine infections, pelvic inflammatory disease, osteomyelitis. Also in combination with vancomycin for the treatment of methicillin-resistant Staphylococcus aureus (MRSA) infection.

Pharmacological effects

1. Broad spectrum antibiotic, high bioavailability, rapid absorption, strong anti-bacterial, not diet affected. Fosfomycin Sodium displays effects on killing Gram-positive and Gram-negative bacteria, especially Pseudomonas aeruginosa, Proteus, Salmonella, and exhibit excellent antibacterial activity for a variety of drug-resistant Staphylococcus aureus and Escherichia coli. For usage in animals, there is no drug resistance and cross-resistance. Clinical effect is good. 2. Rapid sterilization: This product is a rapid fungicide, its role is still evident after 1-2 hours. About 25% of the E. coli were killed at 1 hour after exposured to Fosfomycin Sodium (12.5μg/ml), and all died within 4-6 hours. Pseudomonas aeruginosa and Staphylococcus aureus were also all killed at 4 and 8 hours. 3. Low toxicity, little irritation on the body, no acute toxicity and adverse reactions, no increased burden on the kidney. 4. Low residue: the eliminate time for the muscles and organs to reach the residual standard is 48-72 hours. The above information is edited by the lookchem of Tian Ye.

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.

Usage and dosage

Used in water for livestock and poultry: every 100kg of water added the product 5-10 grams, 2 times a day, once every three days. Used in animal spices: 10-15 g of the product added to per 100kg feed, 2 times a day, once every three days.

Combination therapy

For the treatment of intestinal infections, Fosfomycin Sodium can combine with β-lactam, aminoglycoside. For the treatment of respiratory and lung infections, combining with macrolides, β-lactam. For staph infections, better combined with erythromycin, rifampin. For the treatment of acute respiratory infections, sepsis, peritonitis ect., increase the dose. Need to combine with β-lactams or aminoglycosides.

Detection Indicator

No. Test item Export standard CP2000 Edition 1 Traits: A white crystalline powder, odorless, taste salty white crystalline powder, odorless, salty taste 2 Discriminator: Positive reaction Positive reaction 3 Specific rotation °-4.2 ~-5.5-4.2 ~-5.5 4 Heavy Metal ≤0.0010% 0≤.0010% 5 Content ≥700μ/mg ≥700μ/mg 6 Alkalinity 9.0-10.5 9.0-10.5 7 Weight loss on drying ≤1.0% ≤1.5% (water) 8 Solution clarity ≤No. 3/4 turbidity standards solution ≤No. 1 turbidity standard solution 9 Color of the solution ≤Yellow No. 1 ≤ Yellow No. 1 10 Glycols ≤0.50% ≤0.50% 11 Clarity of solution: can not be detected, in compliance with (a gross point ≤8/g, wherein a color point ≤2/g) 12 W ≤0.002%- 13 phosphorus content-16.2-17.9% 14 Sterile: Subject to compliance 15 Heat source/ bacterial endotoxin: compliance (heat source) compliance (bacterial endotoxin) 16 α-phenylethylamine ≤0.01%- 17 Residual amount of methanol: real 18 Residual amount of ethanol: Real The above information is the main export detection index of fosfomycin.

Precautions

1. This product is mainly used for pigs, chickens, fish; application for other animals should medication under veterinary guidance. 2. Fosfomycin Sodiumand β-lactams, aminoglycosides, macrocyclic acid esters have a synergistic effect of combination therapy, and can reduce or delay the occurrence of bacterial resistance.

Uses

Different sources of media describe the Uses of 26016-99-9 differently. You can refer to the following data:
1. For the treatment of infections caused by Staphylococcus aureus, Escherichia coli, Proteus and Shigella.
2. Curariform muscle relaxants
3. 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
4. Prevents peptidoglycan synthesis by inhibiting MurA, an enzyme responsible for synthesizing N-acetylmuramic acid or NAM, a major component of peptidoglycan

Chemical Properties

White Solid

Check Digit Verification of cas no

The CAS Registry Mumber 26016-99-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,0,1 and 6 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 26016-99:
(7*2)+(6*6)+(5*0)+(4*1)+(3*6)+(2*9)+(1*9)=99
99 % 10 = 9
So 26016-99-9 is a valid CAS Registry Number.
InChI:InChI=1/C3H7O4P.2Na/c1-2-3(7-2)8(4,5)6;;/h2-3H,1H3,(H2,4,5,6);;/q;2*+1/p-2/t2-,3+;;/m0../s1

26016-99-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (F0889)  Fosfomycin Disodium Salt  >98.0%(HPLC)(T)

  • 26016-99-9

  • 5g

  • 790.00CNY

  • Detail
  • TCI America

  • (F0889)  Fosfomycin Disodium Salt  >98.0%(HPLC)(T)

  • 26016-99-9

  • 25g

  • 2,350.00CNY

  • Detail

26016-99-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Fosfomycin Disodium Salt

1.2 Other means of identification

Product number -
Other names Disodium (1R,2S)-1,2-Epoxypropylphosphonate

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:26016-99-9 SDS

26016-99-9Synthetic route

syn-(1R,2S)-1-chloro-2-hydroxypropane phosphonic acid disodium salt

syn-(1R,2S)-1-chloro-2-hydroxypropane phosphonic acid disodium salt

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Conditions
ConditionsYield
With sodium hydroxide for 1h;90%
dibenzyl (1R,2S)-1,2-epoxypropylphosphonate
172585-28-3

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

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Conditions
ConditionsYield
With Dowex 50WX8 (Na form); hydrogen; cyclohexylamine; palladium on activated charcoal In methanol76%
(1-bromo-2-hydroxypropyl)phosphonic acid
119007-50-0

(1-bromo-2-hydroxypropyl)phosphonic acid

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Conditions
ConditionsYield
With sodium methylate In methanol1.91 g
(1R,2S)-1-chloro-2-hydroxypropanephosphonic acid
640716-21-8

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

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Conditions
ConditionsYield
With sodium hydroxide In methanol pH=9 - 10;
disodium (1S,2S)-2-hydroxy-1-methanesulphonyloxypropyl phosphonate

disodium (1S,2S)-2-hydroxy-1-methanesulphonyloxypropyl phosphonate

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Conditions
ConditionsYield
With sodium hydroxide In water
With sodium hydroxide In water
With sodium hydroxide In water
phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

cyclohexylamine
108-91-8

cyclohexylamine

((1R,2R)-1,2-Dihydroxy-propyl)-phosphonic acid; compound with cyclohexylamine
132125-61-2

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

Conditions
ConditionsYield
With sulfuric acid at 50℃; for 48h;60%
phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

A

(1S,2S)-(+)-(1-Amino-2-hydroxypropyl)phosphonsaeure
128708-51-0

(1S,2S)-(+)-(1-Amino-2-hydroxypropyl)phosphonsaeure

B

(1R,2R)-(-)-(2-Amino-1-hydroxypropyl)phosphonsaeure
84601-12-7

(1R,2R)-(-)-(2-Amino-1-hydroxypropyl)phosphonsaeure

Conditions
ConditionsYield
With ammonia at 60℃;A 42%
B 58%
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;
dimethyltin dichloride
753-73-1

dimethyltin dichloride

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Me2Sn((1R,2S)-1,2-epoxypropylphosphonate)

Me2Sn((1R,2S)-1,2-epoxypropylphosphonate)

Conditions
ConditionsYield
In methanol 1:1 mixt. stirred for 24 h at 40°C; pptd. on cooling, septd., recrystd. (benzene/chloroform=1/1), dried overP4O10 (vac.), elem. anal.;
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

(Me3Sn)2((1R,2S)-1,2-epoxypropylphosphonate)

(Me3Sn)2((1R,2S)-1,2-epoxypropylphosphonate)

Conditions
ConditionsYield
In methanol stoich. mixt. stirred for 24 h at 40°C; pptd. on cooling, septd., recrystd. (benzene/chloroform=1/1), dried overP4O10 (vac.), elem. anal.;
dibutyltin chloride
683-18-1

dibutyltin chloride

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Bu2Sn((1R,2S)-1,2-epoxypropylphosphonate)

Bu2Sn((1R,2S)-1,2-epoxypropylphosphonate)

Conditions
ConditionsYield
In methanol 1:1 mixt. stirred for 24 h at 40°C; pptd. on cooling, septd., recrystd. (benzene/chloroform=1/1), dried overP4O10 (vac.), elem. anal.;
phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

triphenyltin chloride
639-58-7

triphenyltin chloride

(Ph3Sn)2((1R,2S)-1,2-epoxypropylphosphonate)

(Ph3Sn)2((1R,2S)-1,2-epoxypropylphosphonate)

Conditions
ConditionsYield
In methanol stoich. mixt. stirred for 24 h at 40°C; pptd. on cooling, septd., recrystd. (benzene/chloroform=1/1), dried overP4O10 (vac.), elem. anal.;
phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

fosfomycin
23155-02-4

fosfomycin

Conditions
ConditionsYield
With Dowex 50x8, H(+) In water
phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

A

(1R,2R) (1,2-dihydroxypropyl)phosphonate

(1R,2R) (1,2-dihydroxypropyl)phosphonate

B

(1S,2S) (1,2-dihydroxypropyl)phosphonate

(1S,2S) (1,2-dihydroxypropyl)phosphonate

Conditions
ConditionsYield
With water; sodium hydroxide at 90℃; for 24h;

26016-99-9Relevant articles and documents

Asymmetric synthesis of (-)-fosfomycin and its trans-(1S,2S)-diastereomer using a biocatalytic reduction as the key step

Marocco, Christian P.,Davis, Erik V.,Finnell, Julie E.,Nguyen, Phung-Hoang,Mateer, Scott C.,Ghiviriga, Ion,Padgett, Clifford W.,Feske, Brent D.

, p. 1784 - 1789 (2011)

Fosfomycin is a gram positive and gram negative antibiotic that contains an asymmetric epoxide. An enzyme library was screened for its ability to reduce dimethyl(1-chloro-2-oxopropyl)phosphonate to the corresponding asymmetric chlorohydrin. Homology models were built in MOE, which were shown to accurately model the enzyme-substrate complex displaying the stereoselectivity that we observed. Two enzymes, YDR368w and YHR104w, were chosen for the scale up and synthesis of fosfomycin and its trans-(1S,2S)-diastereomer.

Silicon Directed Asymmetric Synthesis of (1R,2S)-(-)-(1,2-Epoxypropyl)phosphonic Acid (Fosfomycin) from (S)-Lactaldehyde

Bandini, Elisa,Martelli, Giorgio,Spunta, Giuseppe,Panunzio, Mauro

, p. 2127 - 2130 (2007/10/03)

The title compound is obtained in high diastereomeric purity based on the stereoselective addition of trimethylsilyldibenzylphosphite (TMSDBP) to O-triisopropylsilyloxy (S)-lactaldehyde.

First asymmetric synthesis of enantiomerically pure (1R,2S)-(-)-(1,2-epoxypropyl)phosphonic acid (fosfomycin)

Giordano,Castaldi

, p. 1470 - 1473 (2007/10/02)

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