144790-28-3

Usage

Uses

Used in Pharmaceutical Industry:
L-Cefadroxil is used as an antibiotic for the treatment of various bacterial infections. Its application is primarily due to its ability to inhibit bacterial cell wall synthesis, leading to the destruction of the bacterial cell. This makes L-Cefadroxil a crucial component in the fight against bacterial infections and a key player in the development of new antibiotics to combat drug-resistant strains.

Upstream product

• 22252-43-3 3-deacetyloxy-7-aminocephalosporanic acid 
• 78858-51-2 C₁₆H₁₉NO₇ 
• 37763-23-8 D-2-p-hydroxyphenylglycine methyl ester 
• 69651-48-5 N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine 
• 541-41-3 chloroformic acid ethyl ester 
• 54397-23-8 D-(-)-4-hydroxyphenylglycineamide 
• 26395-99-3 7-aminodesacetoxycephalosporanic acid 

Downstream Products

• 73226-86-5 2-hydroxy-3-(p-hydroxyphenyl)-6-methylpyrazine 
• 147103-95-5 4-hydroxyphenylglycylcefadroxil 
• 34876-35-2 3-hydroxy-4-methyl-2(5H)-thiophenone 
• 135656-64-3 7-<2-(dihydro-5-butyl-6-thioxo-2H-1,3,5-thiadiazine-3(4H)-yl)-2-(4-hydroxyphenyl)acetamido>-3-methyl-3-cephem-4-carboxylic acid 
• 135656-67-6 7-<2-(dihydro-5-isobutyl-6-thioxo-2H-1,3,5-thiadiazine-3(4H)-yl)-2-(4-hydroxyphenyl)acetamido>-3-methyl-3-cephem-4-carboxylic acid 

Relevant academic research and scientific papers

Clathration-induced asymmetric transformation of cefadroxil

The cephalosporin antibiotic Cefadroxil can be epimerized at the α-carbon of its amino acid side chain using pyridoxal as the mediator. By clathration with 2,7-dihydroxynaphthalene, the desired diastereomer can be selectively withdrawn from the equilibrat

Efficient synthesis of cefadroxil in [Bmim][NTf2]-phosphate cosolvent by magnetic immobilized penicillin G acylase

For the first time, cefadroxil was synthesized from 7-Amino-3-desacetoxycephalosporanic acid and d-hydroxyphenylglycine methyl ester in [Bmim][NTf2]-phosphate cosolvent capable of dissolving the substrates using the penicillin G acylase (PGA) immobilized on the micrometer-size magnetic polymer microspheres having high activity of 2,083 U/g. The high synthesis/hydrolysis (S/H) ratio of 1.12 was achieved with 79.0% yield, where only the S/H ratio of 0.19 and yield of 20.0% was obtained using free PGA under the identical optimum reaction conditions. Cefadroxil had been synthesized efficiently in [Bmim][NTf2]-phosphate cosolvent by the magnetic immobilized PGA, which illuminated that there are two very critical and essential designs, that is, effective support and suitable solvent system by PGA, in enzymatic synthesis of cefadroxil. Obviously, there is great potential for the magnetic immobilized PGA and ionic liquid solvent in application to biocatalysis.

PROCESS FOR THE SYNTHESIS OF HYDROXYPHENYLGLYCINE ESTERS

The present invention refers to a process for the synthesis of a D-(-)-p-hydroxyphenylglycine (HPG) ester in crystal form, by crystallizing D-HPG ester from a solution containing dissolved D-HPG ester to obtain a suspension comprising D-HPG ester crystals, characterized in that the eeD of the D-HPG ester in the solution and the eeD of the D-HPG ester crystals is above 95%, preferably above 97%, more preferably above 98%, more preferably above 99%, more preferably above 99.5%.

PROCESS FOR THE CRYSTALLISATION OF CEFADROXIL

The present invention relates to a process for the preparation of cefadroxil in crystal form, comprising a) adding an aqueous solution of cefadroxil to a crystallisation vessel and a titrant to keep a pH in the crystallisation vessel of between 7 to 9; and b) lowering the pH in the crystallisation vessel to a value of between 5 and 6.5 to obtain a suspension of the ?-lactam compound in crystal form. The invention further relates to cefadroxil in crystal form obtainable by the process according to the present invention. The invention also relates to cefadroxil in crystal form with a CIE b value of below 12 when stored at a temperature of 25°C for at least 1 month.

PROCESSES FOR THE PREPARATION OF CEPHEM DERIVATIVES

Provided is a process for preparing a compound of formula 1 or its salt, which includes reacting a compound of formula 2 with a compound of formula 3 in the presence of a base.

PROCESS FOR THE PREPARATION OF 7-AMINO (p-HYDROXYPHENYLGLYCYL) CEPHEM COMPOUNDS

The invention relates to pure 7- amino (p-hydroxyphenylglycyl) cephem compounds. The invention also relates to processes for the preparation of pure 7- amino (p-hydroxyphenylglycyl) cephem compounds and pharmaceutical compositions that include the pure 7- amino (p-hydroxyphenylglycyl) cephem compounds.

Process for the preparation of cefadroxil

The present invention relates to an improved process for the preparation of cefadroxil of the formula (I), more particularly, the present invention relates to an improved process for the preparation of cefadroxil having water content in the range of 4-5%.

Synthesis of cephalosporin-type antibiotics by coupling of their β-lactam nucleus and racemic amino acid side chains using a clathration-induced asymmetric transformation

The cephalosporin-type antibiotics Cephalexin, Cephradine and Cefadroxil have been prepared by coupling of their β-lactam nucleus and racemic amino acid side chain precursors. The initially obtained mixture of cephalosporin epimers is subjected to a clathration-induced asymmetric transformation which results in the epimerization of the epi-cephalosporin into the cephalosporin with the correct diastereomeric configuration.

Penicillin acylase in the industrial production of β-lactam antibiotics

Immobilized penicillin acylase is a biocatalyst suitable for the kinetically controlled industrial synthesis of semi-synthetic antibiotics in aqueous environments. Amoxiciliin and ampicillin are obtained by condensing 6-aminopenicillanic acid with the amide or ester of D-( - )-4-hydroxyphenyIglycine and D-( - )phenylglycine, respectively. Similarly, the cephalosporin antibiotics cefadroxil and cephalexin can be obtained from 7-aminodesacetoxycephalosporanic acid.

Synthesis of related substances of cefadroxil

The chemical synthesis of some related substances of the cephalosporin antibiotic cefadroxil is described. These compounds which may be present in commercial samples originate from the semisynthetic preparation of the antibiotic or from degradation. The preparation of these products enables the validation of selective quantitative analytical methods, such as liquid chromatography and tlc.