144125-09-7

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(S*)]]-
• CAS NO: 144125-09-7
• Molecular Formula: C₁₈H₁₈N₆O₅S₂
• Molecular Weight: 462.5
• Mol File: 144125-09-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: cefamandole(CAS DataBase Reference)
• NIST Chemistry Reference: cefamandole(144125-09-7)
• EPA Substance Registry System: cefamandole(144125-09-7)

Safety Data

• Hazardous Substances Data: 144125-09-7(Hazardous Substances Data)

Usage

Description

Cefamandole is a second-generation cephalosporin antibiotic characterized by its potent antibacterial activity. It is a stereoisomer of Cefamandole (C440145) and is primarily used in the medical field to combat bacterial infections.

Uses

Used in Medical Industry:
Cefamandole is used as an antibiotic for treating a variety of bacterial infections. Its application is particularly effective against gram-positive and some gram-negative bacteria, making it a valuable tool in the treatment of infections caused by these types of bacteria.

Upstream product

• 42540-40-9 Bergacef 
• 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 
• 51818-85-0 7-[(1-hydroxy-1-phenyl)-acetamido]-3-acetoxymethyl-Δ³-cephem-4-carboxylic acid 
• 13183-79-4 1-methyl-5-mercaptotetrazole 
• 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 
• 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 
• 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 
• 70579-79-2 (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 
• 70579-78-1 (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 
• 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 
• 57268-80-1 Cefamandole nafate 
• 42540-40-9 cefamandole nafate 

Relevant articles and documents

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.

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

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.