65338-32-1

Basic information

• Product Name: cefamandole
• Synonyms: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[(hydroxyphenylacetyl)amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, [6R-(6α,7β)]-
• CAS NO: 65338-32-1
• Molecular Formula: C₁₈H₁₈N₆O₅S₂
• Molecular Weight: 462.5
• Mol File: 65338-32-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: cefamandole(CAS DataBase Reference)
• NIST Chemistry Reference: cefamandole(65338-32-1)
• EPA Substance Registry System: cefamandole(65338-32-1)

Safety Data

• Hazardous Substances Data: 65338-32-1(Hazardous Substances Data)

Upstream product

• 51818-85-0 7-[(1-hydroxy-1-phenyl)-acetamido]-3-acetoxymethyl-Δ³-cephem-4-carboxylic acid 
• 13183-79-4 1-methyl-5-mercaptotetrazole 
• 20698-91-3 (R)-methyl mandelate 
• 24209-38-9 (6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid 
• 42540-40-9 cefamandole nafate 

Downstream Products

• 58333-59-8 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester 
• 70579-75-8 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-glycyloxymethyl ester 
• 57268-80-1 Cefamandole nafate 
• 42540-40-9 cefamandole nafate 
• 70606-86-9 N-tert-butoxycarbonyl-L-aspartic acid 4-[(6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyloxymethyl] ester 1-methyl ester 
• 70579-78-1 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-L-isoleucyloxymethyl ester 
• 70579-79-2 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (N-tert-butoxycarbonyl-L-phenylalanyloxy)-methyl ester 
• 70579-77-0 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-L-leucyloxymethyl ester 
• 70579-76-9 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-L-valyloxymethyl ester 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF CEFAMANDOLE NAFATE

The present invention relates to a process for the preparation of cefamandole nafate from cefamandole and to the use thereof in the manufacture of a medicament for treatment of a bacterial disease.

PROCESS FOR THE FORMYLATION OF CEFAMANDOLE

The present invention relates to a process for the preparation of O-formyl cefamandole, an intermediate in the preparation of cefamandole nafate, by formylation of cefamandole.

Coupling of Site-Directed mutagenesis and immobilization for the rational design of more efficient biocatalysts: The case of immobilized 3G3K PGA from E. coli

We have investigated the synthetic performance of the immobilized 3G3K mutant of the Penicillin G acylase (PGA) from E. coli obtained by site-directed mutagenesis. The 3G3K mutant, characterized by a tag consisting of three lysines alternating with three

Influence of substrate structure on PGA-catalyzed acylations. Evaluation of different approaches for the enzymatic synthesis of cefonicid

The influence of the substrate structure on the catalytic properties of penicillin G acylase (PGA) from Escherichia coli in kinetically controlled acylations has been studied. In particular, the affinity of different β-lactam nuclei towards the active site has been evaluated considering the ratio between the rate of synthesis (vs) and the rate of hydrolysis of the acylating ester (vhl). 7-Aminocephalosporanic acid (7-ACA) and 7-amino-3-(1-sulfomethyl-1,2,3,4-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (7-SACA) showed a good affinity for the active centre of PGA. The enzymatic acylation of these nuclei with R-methyl mandelate has been studied in order to evaluate different approaches for the enzymatic synthesis of cefonicid. The best results have been obtained in the acylation of 7-SACA. Cefonicid (8) was recovered from the reaction mixture as the disodium salt in 65% yield and about 95% of purity. Furthermore, through acylation of 7-ACA, a "one-pot" chemo-enzymatic synthesis was carried out starting from cephalosporin C using three enzymes in sequence: D-amino acid oxidase (DAO), glutaryl acylase (GA) and PGA. Cefonicid disodium salt was obtained in three steps, avoiding any intermediate purification, in 35% overall yield and about 94% purity. This approach presents several advantages compared with the classical chemical processes.

Modulation of penicillin acylase properties via immobilization techniques: One-pot chemoenzymatic synthesis of Cephamandole from Cephalosporin C

The modulation of penicillin G acylase (PGA) properties via immobilization techniques has been performed studying the acylation of 7-aminocephalosporanic acid with R-mandelic acid methyl ester. PGA from Escherichia coli, immobilized onto agarose activated

Prodrug derivatives of carboxylic acid drugs

Novel ester derivatives of carboxylic acid medicaments of formula (I), wherein R--COO--represents the acyloxy residue of a carboxylic acid drug or medicament, n is an integrer from 1 to 3, and R1 and R2 are the same or different and are selected from a group consisting of an alkyl, an alkenyl, an aryl, an aralkyl, a cycloalkyl and which group may be unsubstituted or substituted, or R1 and R2 together with the N forms a 4-, 5-, 6- or 7-membered heterocyclic ring, which in addition to the nitrogen atom may contain one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and which heterocyclic group may be substituted. These compounds are highly biolabile prodrug forms of the corresponding carboxylic acid compounds and are highly susceptible to undergoing enzymatic hydrolysis in vivo whereas they are highly stable in aqueous solution. The novel derivatives are less irritating to mucosa than the parent carboxylic acids and may provide an improved bio-availability of the drugs.

Sparingly soluble salts of cefamandole, and ophthalmic compositions containing same

The hydrabamine and benzathine salts of cefamandole are useful in aqueous ophthalmic compositions which have good stability and shelf life.

Conversion of cefamandole nafate to cefamandole sodium

The rate of hydrolysis of the formyl moiety of cefamandole nafate was determined as a function of pH, temperature, and concentration of added sodium carbonate or tromethamine. The reaction rate was sensitive to hydroxide ion in the pH 5.5-8.0 range with half life values of hours to minutes. Hydrolysis was rapid upon the addition of sodium carbonate or tromethamine. Chirality in the 7 D mandelamido side chain was unaffected by hydrolysis.