42540-40-9

Basic information

• Product Name: Cemandil sodium salt
• Synonyms: ,(6r-(6-alpha,7-beta(r)))-;5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicacid,7-(((formyloxy)phenylace;cefamandolnafato;cephamandolenafate;mandol;o-formylcefamandolesodium;CEFAMANDOLE FORMATE SODIUM SALT;CEFAMANDOLE NAFATE
• CAS NO: 42540-40-9
• Molecular Formula: C₁₉H₁₇N₆O₆S₂*Na
• Molecular Weight: 512.49
• EINECS: 255-877-4
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;MANDOL
• Mol File: 42540-40-9.mol

Chemical Properties

• Melting Point: 190-193°C
• Appearance: White solid
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility: Freely soluble in water, sparingly soluble in methanol.
• PKA: 2.6-3.0(at 25℃)
• Water Solubility: Freely soluble in water. Sparingly soluble in methanol
• CAS DataBase Reference: Cemandil sodium salt(CAS DataBase Reference)
• NIST Chemistry Reference: Cemandil sodium salt(42540-40-9)
• EPA Substance Registry System: Cemandil sodium salt(42540-40-9)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: XI0380000
• Hazardous Substances Data: 42540-40-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cemandil sodium salt is used as an antibiotic for treating various bacterial infections. Its application is due to its effectiveness in combating a wide range of bacterial pathogens, making it a valuable asset in the fight against infections.
Used in Medical Treatments:
Cemandil sodium salt is used as a therapeutic agent for patients suffering from bacterial infections. Its application is based on its ability to inhibit bacterial cell wall synthesis, leading to the destruction of the bacterial cell and the resolution of the infection.
Used in Research and Development:
Cemandil sodium salt is used as a research compound for studying the mechanisms of action and resistance of cephalosporin antibiotics. Its application in this context is to further understand the interactions between antibiotics and bacterial cells, potentially leading to the development of more effective treatments.

Therapeutic Function

Antibiotic

Mechanism of action

Cefamandole nafate has a formylated D-mandelic amide moiety at C-7. The formate ester is cleaved rapidly in the host to release the more active cefamandole. The esterification also apparently overcomes the instability of cefamandole when it is stored in dry form. This agent has increased activity against Haemophil us influenzae and some Gram-negative bacilli as compared with the first-generation cephalosporins. Loss of the 5-thio-l-methyl-l-H-tetrazole moiety (referred to sometimes by the acronym MT T) from C-3 is associated with prothrombin deficiency and bleeding problems as well as with an Antabuse-like acute alcohol intolerance. On the other hand, this grouping enhances potency and prevents metabolism by deacetylation. Like the other second-generation cephalosporins, cefamandole is more active against Gram-negative bacteria. The principle clinical use is for lower respiratory tract, skin and skin structures, and bone and joint infections as well as septicemia and urinary tract infections when the organisms are sensitive.

Clinical Use

The D-mandeloyl moiety of Cemandil sodium salt appears toconfer resistance to a few β-lactamases, since some β-lactamase–producing, Gram-negative bacteria (particularlyEnterobacteriaceae) that show resistance to cefazolin andother first-generation cephalosporins are sensitive tocefamandole. Additionally, it is active against some ampicillin-resistant strains of Neisseria and Haemophilus spp.Although resistance to β-lactamases may be a factor in determiningthe sensitivity of individual bacterial strains tocefamandole, an early study indicated that other factors,such as permeability and intrinsic activity, are frequentlymore important. The L-mandeloyl isomer is significantlyless active than the D-isomer.

InChI:InChI=1/C19H18N6O6S2.Na/c1-24-19(21-22-23-24)33-8-11-7-32-17-12(16(28)25(17)13(11)18(29)30)20-15(27)14(31-9-26)10-5-3-2-4-6-10;/h2-6,9,12,14,17H,7-8H2,1H3,(H,20,27)(H,29,30);/q;+1/p-1/t12-,14-,17-;/m1./s1

Upstream product

• 24209-38-9 (6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid 
• 20698-91-3 (R)-methyl mandelate 
• 65338-32-1 cefamandole 
• 57268-80-1 Cefamandole nafate 
• 29169-63-9 (R)-formiloxy(phenyl)acetic acid 
• 80543-51-7 (S)-formyloxy(phenyl)acetyl chloride 
• 957-68-6 7-Aminocephalosporanic acid 
• 22252-43-3 3-deacetyloxy-7-aminocephalosporanic acid 
• 57079-45-5 D-(-)-2-formyloxy-2-phenylacetyl chloride 

Downstream Products

• 65338-32-1 cefamandole 
• 144125-09-7 cefamandole 
• 65338-32-1 cefamandole 

Relevant articles and documents

Synthetic method of L-type cefamandole nafate

The invention provides a synthesis method of L-type cefamandole nafate, which comprises the following steps of carrying out silanization reaction on 7-ATCA and a silane protective agent in the presence of an organic solvent, carrying out acylation reaction with L-formyl mandelic acid chloride, removing silane protective groups, carrying out salification reaction with a sodium salt solution, and carrying out freeze drying to obtain an L-type cefamandole nafate solid. The invention provides an efficient and simple synthetic method of L-type cefamandole nafate.

1/4 head spore Meng Duozhi sodium compound (by machine translation)

The invention discloses 1/4 head spore Meng Duozhi sodium compound and its preparation method, each of the plurality of containing sodium molar spore Meng 1/4 mole water. The method of the invention for preparing the compounds of the spore Meng Duozhi sodium, low impurity content, good stability, and good fluidity, the moisture and small, with more extensive application prospects. (by machine translation)

Synthesis method for dextrorotation cefamandole nafate

The invention discloses a synthesis method for dextrorotation cefamandole nafate. The method includes the steps that in one-element organic solvent, 7-ACA and 1-methyl-1h-tetrazole-5-thiol are subjected to condensation with a boron trifluoride complex of the one-element organic solvent as a catalyst so as to generate 7-ATCA; and then, in another one-element organic solvent, under the effect of organic alkali, the 7-ATCA and S-(-)-formylmandeloyl chloride are made to react so as to generate the dextrorotation cefamandole nafate, then, an organic phase is left after hydrolysis and extraction phase splitting, organic acid sodium salt and another organic solvent indissolvable in dextrorotation cefamandole sodium are added, the dextrorotation cefamandole sodium is obtained through crystallization, finally, the dextrorotation cefamandole sodium is dissolved in water, organic solvent incapable of being dissolved in water is added together with organic or inorganic acid, an organic phase is left after extraction phase splitting, and reduced pressure rotary evaporation is conducted on the organic phase to obtain the dextrorotation cefamandole nafate. The method is simple, conditions are gentle, raw materials are easy to obtain, and purity of the finally-obtained product is 99% or above.

Method for improving quality of cemandil sodium by using three-dimensional column plate to purify solvent

The present invention discloses a method for improving the quality of cemandil sodium by using a three-dimensional column plate to purify a solvent. The method comprises: solvent purification, alkylation reaction, cefamandole ester synthesis, extraction, cemandil sodium synthesis, and sterile sub-packaging. According to the present invention, during the cemandil sodium preparation process, the reaction system solvent is purified by using the high-throughput efficient three-dimensional mass transfer column tray technology so as to finally improve the quality of the cemandil sodium product and ensure the quality of the cemandil sodium powder-needle preparation for injection. The invention provides the method for improving the quality of the cemandil sodium powder-needle preparation for injection by using the three-dimensional column tray mass transfer technology to purify the organic solvent.

Cefamandole nafate for reducing anaphylaxis and preparation thereof

The invention relates to an antibiotic drug, in particular to cefamandole nafate for reducing anaphylaxis. The compound has the advantages of high yield, high purity and the like, and is suitable for industrial production, and product stability and anaphylaxis reducing and clinic application of a preparation are all obviously improved .

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.