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HomeProduct name listCemandil sodium salt

Cemandil sodium salt

Synonym(s):Cefamandole formate sodium salt

  • CAS NO.:42540-40-9
  • Empirical Formula: C19H17N6NaO6S2
  • Molecular Weight: 512.49
  • MDL number: MFCD00864877
  • EINECS: 255-877-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-07-02 08:55:11
Cemandil sodium salt Structural

What is Cemandil sodium salt?

Chemical properties

White Solid

Originator

Mandokef,Lilly,W. Germany,1977

The Uses of Cemandil sodium salt

Cephalosporin antibacterial.

The Uses of Cemandil sodium salt

A second generation cephalosporin antibiotic.

What are the applications of Application

Cefamandole nafate is a compound used to study the effects of expression and inhibition of PBP 2A

Definition

ChEBI: A cephalosporin prodrug having (R)-O-formylmandelamido and N-methylthiotetrazole side-groups.

Manufacturing Process

To 21.6 kg (17.8 l) of 98% formic acid was added 1.14 kg (7.5 mols) of D-(-)- mandelic acid and the reaction mixture was heated for 4 hours at 70°C with stirring. The excess formic acid was evaporated off in vacuo and the residual syrup was dissolved in 6 l of benzene. The solution was washed twice with 6 l portions of water and was dried over magnesium sulfate. The drying agent was filtered and washed with 1.5 l of benzene, the washes being added to the filtrate. The dried filtrate was evaporated in vacuo to obtain the D-(-)- mandelic acid formate ether as a syrup. The product can be crystallized from cyclohexane to yield material melting at about 55°C to 58°C.
The mandelic acid formate ester obtained as a syrup as described above is stirred for 2 hours with 2.9 kg (~1.75 l) of thionyl chloride at a temperature of about 70°C. The excess thionyl chloride is removed by evaporation and the residual green solution is vacuum distilled. The product, O-formyl mandeloyl chloride, distills over at 127°C to 130°C (15 mm) or at 108°C to 112°C (7 mm).
To 13 l of ethyl acetate were added 85.1 g (2.59 mols) of 7-amino-3-(1- methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid and 1,361 g (10.37 mols) of monotrimethylsilyl acetamide, and the mixture was stirred at 50°C until a clear solution was obtained. The solution was cooled to 20°C and 514 g (2.59 mold of O-formyl mandeloyl chloride was added at a rate such that the temperature of the reaction solution was maintained between about 20°C to 25% with ice-cooling.
The reaction mixture was stirred for 1.5 hours at about room temperature after the addition of the mandeloyl chloride was completed. Five liters of water were then added to the reaction mixture and the diluted mixture was stirred for about 10 minutes. The organic layer was separated and was washed twice with water. The combined washes are extracted with 1.5 l of ethyl acetate and the extract is combined with the washed organic layer. The whole was dried over magnesium sulfate, filtered and evaporated in vacuo on a 25°C water bath to yield 1,460 g of product, 7-(D-2-formyloxy-2- phenylacetamido)-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4- carboxylic acid, as a yellow foam.
The product was dissolved in 5 l of acetone and the solution was mixed with a solution of 430 g (2.59 mols) of sodium 2-ethylhexanoate in 5.4 l of acetone. The combined solutions were seeded and stirred in an ice bath for 1.5 hours. The crystalline precipitate of sodium 7-(D-2-formyloxy-2-phenylacetamido)-3- (1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate was filtered and washed with 5 l of acetone. The crystalline salt was dried overnight in a vacuum oven at 40°C to yield 1,060 g (80%)of product, melting at 182°C to 184°C.

brand name

Mandol (Lilly).

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.

Properties of Cemandil sodium salt

Melting point: 190-193°C
storage temp.  Inert atmosphere,Store in freezer, under -20°C
solubility  Freely soluble in water, sparingly soluble in methanol.
form  neat
pka 2.6-3.0(at 25℃)
form  Solid
color  White to Off-White
Water Solubility  Freely soluble in water. Sparingly soluble in methanol
CAS DataBase Reference 42540-40-9(CAS DataBase Reference)

Safety information for Cemandil sodium salt

Signal word Danger
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H315:Skin corrosion/irritation
H317:Sensitisation, Skin
H319:Serious eye damage/eye irritation
H334:Sensitisation, respiratory
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P284:Wear respiratory protection.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P342+P311:IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

Computed Descriptors for Cemandil sodium salt

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