Cemandil sodium salt

Base Information

• Chemical Name: Cemandil sodium salt
• CAS No.: 42540-40-9
• Molecular Formula: C19H18N6O6S2. Na
• Molecular Weight: 512.502
• Hs Code.: 2941906000
• Mol file: 42540-40-9.mol

Synonyms:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[(2R)-(formyloxy)phenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,monosodium salt, (6R,7R)- (9CI);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(formyloxy)phenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,monosodium salt, [6R-[6a,7b(R*)]]-;Bergacef;Cedol;Cefam;Cefamandole formate sodium;Cefamandole nafate;Cefiran;Cemado;Cemandil;Fado;Kefadol;Kefandol;Lampomandol;Mandokef;Mandolsan;O-Formylcefamandole sodium;Sodium7-(D-2-formyloxy-2-phenylacetamido)-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate;Sodium O-formylcefamandole;

Chemical Property of Cemandil sodium salt

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 190-193 °C
• PKA: 2.6-3.0(at 25℃)
• PSA: 210.04000
• LogP: -0.41490
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: Freely soluble in water, sparingly soluble in methanol.
• Water Solubility.: Freely soluble in water. Sparingly soluble in methanol

Purity/Quality:

99% ^*data from raw suppliers

Cefamandole nafate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 26-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Uses: A second generation cephalosporin antibiotic. Cephalosporin antibacterial.
• Therapeutic Function: Antibiotic
• 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.

Technology Process of Cemandil sodium salt

There total 11 articles about Cemandil sodium salt which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.3%

(S)-formyloxy(phenyl)acetyl chloride (80543-51-7) + (6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid (24209-38-9) → cefamandole nafate (42540-40-9)

Guidance literature:

(6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid; With N,O-bis-(trimethylsilyl)-acetamide; In ethyl acetate; at 25 - 28 ℃;

(S)-formyloxy(phenyl)acetyl chloride; In ethyl acetate; at 0 - 5 ℃; for 2h;

With sodium hydrogencarbonate; pH=5.5 - 6.5; Solvent; Temperature;

Reference yield:

Cefamandole nafate (57268-80-1) → cefamandole nafate (42540-40-9)

Guidance literature:

With sodium 2-ethylhexanoic acid; In isopropyl alcohol; acetone; at 20 ℃; pH=5.6; pH-value; Solvent;

Reference yield:

D-mandelic acid chloride oxalate + (6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid (24209-38-9) → cefamandole nafate (42540-40-9)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at 2 - 20 ℃; for 3h;

upstream raw materials:

(6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid

(R)-methyl mandelate

cefamandole

Cefamandole nafate

Downstream raw materials:

cefamandole

cefamandole

cefamandole

Refernces

• 1、 -. "Method for improving quality of cemandil sodium by using three-dimensional column plate to purify solvent". . . Retrieved 2017/05/10.
• 2、 -. "Synthesis method for dextrorotation cefamandole nafate". Paragraph 0020; 0021. . Retrieved 2017/08/28.