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Ceftezole

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Ceftezole Basic information

Product Name:
Ceftezole
Synonyms:
  • ceftezol
  • CEPHTEZOL
  • CEFTEZOLE
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-3-[(1,3,4-thiadiazol-2-ylthio)methyl]-, (6R,7R)-
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-3-[(1,3,4-thiadiazol-2-ylthio)methyl]-, (6R-trans)-
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 8-oxo-7-[2-(1H-tetrazol-1-yl)acetamido]-3-[(1,3,4-thiadiazol-2-ylthio)methyl]- (8CI)
  • Celoslin
  • CG-B 3Q
CAS:
26973-24-0
MF:
C13H12N8O4S3
MW:
440.48
Mol File:
26973-24-0.mol
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Ceftezole Chemical Properties

Melting point:
155°C (dec.)
Density 
2.09
pka
2.60±0.50(Predicted)
λmax
273nm(Phosphate buffer sol.)(lit.)
Merck 
14,1948
CAS DataBase Reference
26973-24-0(CAS DataBase Reference)
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Safety Information

Hazard Codes 
T+,N
Risk Statements 
21/22-26-50/53
Safety Statements 
28-36/37-45-61
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Ceftezole Usage And Synthesis

Originator

Ceftezole,Arocor Holdings Inc.

Manufacturing Process

To a solution of 1 equivalent (eq.) of 1H-tetrazole-1-acetic acid and 1 eq. of triethylamine in 20 ml of tetrahydrofuran cooled to -20°C was added 1 eq. of pivaloyl chloride. After thirty-minute stirring of the mixture 20 ml of a chloroform solution containing 1 eq. of and 1 eq. of triethylamine was poured into the solution cooled at -10°C during a period of 30 minutes. The resulting mixed solution was stirred for 30 minutes at the same temperature, for 1 hour in an ice-water mixture and for 3 hours at room temperature. Removal of a solvent from the reaction mixture afforded an oily residue, which was dissolved into 15 ml of 10% sodium bicarbonate aqueous solution. The resulting aqueous layer was adjusted to pH 1.0-2.0 with 10% hydrochloric acid, washed with ether and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate and concentrated under reduced pressure leaving a residue which was triturated with ethyl acetate to obtain 3- acetoxymethyl-8-oxo-7-(2-tetrazol-1-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid.
A solution of 1 eq. of sodium salt of 3-acetoxymethyl-8-oxo-7-(2-tetrazol-1- acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (it may be prepared with equivalent of sodium bicarbonate and above named acid) and 1 eq. of [1.3.4]-thiadiazole-2-thiol in 20 ml of phosphate buffer (pH 6.4) was stirred for 5.5 hours at 60°C. The reaction mixture was adjusted to pH 2.0 with 5% hydrochloric acid and treated with ethyl acetate to form a title compound - ceftezole.

Therapeutic Function

Antibiotic

CeftezoleSupplier

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