42540-40-9 Usage
Chemical Properties
White Solid
Uses
Different sources of media describe the Uses of 42540-40-9 differently. You can refer to the following data:
1. A second generation cephalosporin antibiotic.
2. Cephalosporin antibacterial.
Definition
ChEBI: A cephalosporin prodrug having (R)-O-formylmandelamido and N-methylthiotetrazole side-groups.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 42540-40-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,2,5,4 and 0 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 42540-40:
(7*4)+(6*2)+(5*5)+(4*4)+(3*0)+(2*4)+(1*0)=89
89 % 10 = 9
So 42540-40-9 is a valid CAS Registry Number.
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
42540-40-9Relevant articles and documents
Synthetic method of L-type cefamandole nafate
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Paragraph 0057-0064, (2021/04/26)
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.
Synthesis method for dextrorotation cefamandole nafate
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, (2017/08/28)
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.
Cefamandole nafate for reducing anaphylaxis and preparation thereof
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Paragraph 0024, (2016/12/01)
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 .
