| Identification | More | [Name]
Ceftezole | [CAS]
26973-24-0 | [Synonyms]
(6r,7r)-8-oxo-7-[(1h-tetrazol-1-ylacetyl)amino]-3-[(1,3,4-thiadiazol-2-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CEFTEZOLE
CEPHTEZOL
ceftezol
Ceftazole
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
CTZ
FR 10123
(6R,7R)-8-Oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-3-[(1,3,4-thiadiazol-2-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | [Molecular Formula]
C13H12N8O4S3 | [MDL Number]
MFCD00274176 | [Molecular Weight]
440.48 | [MOL File]
26973-24-0.mol |
| Hazard Information | Back Directory | [Originator]
Ceftezole,Arocor Holdings Inc. | [Uses]
A direct bandgap semiconductor, it is used in a variety of applications, including radiation detectors, photorefractive gratings, electro-optic modulators, solar cells, and terahertz generation and detection. The band gap varies from approximately 1.4 to 2.2 eV, depending on composition. | [Uses]
Ceftezole is a β-lactam, cephem antibiotic. It also exhibits potent α-glucosidase inhibitory activity and antidiabetic effect in streptozotocin-induced mouse. | [Definition]
ChEBI: Ceftezole is a first-generation cephalosporin antibiotic having (1,3,4-thiadiazol-2-ylsulfanyl)methyl and [2-(1H-tetrazol-1-yl)acetamido side groups located at positions 3 and 7 respectively. It is a cephalosporin and a member of thiadiazoles. | [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 | [General Description]
Cadmium zinc telluride (Cd1-xZnxTe or CZT) can detect nuclear radiation hence, CZT with Zn concentrations between 0.1-0.2 may be used in the making of radiation detectors of X-ray and gamma-ray spectrometers. |
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