cefacetrile Chemical Properties

Melting point:

133-135°C

Boiling point:

757.5±60.0 °C(Predicted)

Density 

1.59±0.1 g/cm3(Predicted)

storage temp. 

Hygroscopic, -20°C Freezer, Under Inert Atmosphere

solubility 

DMF (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

pKa 1.97 (Uncertain)

form 

Solid

color 

White to Pale Beige

Stability:

Hygroscopic

cefacetrile Usage And Synthesis

Description

This drug is similar to cephalothin, but after intravenous administration, higher peak serum levels are attained, and its serum half-life is longer (Brogard et al., 1973a; Brogard et al., 1973b). However, cephacetrile appears to have no clinical advantages over cephalothin, as demonstrated in one comparative trial (Jackson et al., 1974). It has most recently been available in Italy.

Chemical Properties

Pale Beige Solid

Originator

Celospor,Ciba Geigy,Switz.,1969

Uses

A cephalosporin antibiotic. Antibacterial.

Definition

ChEBI: Cefacetrile is a cephalosporin.

Manufacturing Process

13.6 g (0.05 mol) of 7-aminocephalosporanic acid are taken up in a mixture of 150 ml of methylene chloride and 19.5 ml of tributylamine (0.12 mol) and at 0°C a solution of 8.4 g of cyanoacetylchloride (0.07 mol) in 100 ml of methylene chloride is stirred in. The bath is then stirred for ? hour at 0°C and for ? hour at 20°C, the reaction solution is evaporated under vacuum and the residue taken up in 10% aqueous dipotassium hydrogenphosphate solution. This aqueous phase is washed with ethyl acetate, acidified to pH 2.0 with concentrated hydrochloric acid and extracted with ethyl acetate.
After having been dried over sodium sulfate and evaporated under vacuum, this extract gives as a solid residue 14.7 g of crude 7-cyanoacetylamino-cephalosporanic acid which is purified by chromatography on 30 times its own weight of silica gel. The fractions eluted with chloroform plus acetone (7:3) furnish a product which crystallizes from acetone plus ether in the form of needles melting at 168° to 170°C with decomposition.
5.10 g (15 mmol) of 7-cyanoacetyl-aminocephalosporanic acid are suspended in 102 ml of distilled water and converted into the sodium salt by stirring in dropwise 15 ml of N sodium hydroxide solution.

Therapeutic Function

Antibiotic

Antimicrobial activity

Its spectrum resembles that of cefalotin. Following an intramuscular dose of 1 g, a peak plasma concentration around 15 mg/L is achieved at 1 h. About 25% is bound to plasma protein. Penetration into the CSF is limited. About 80% of the drug is excreted in the urine, producing concentrations in excess of 1 g/L, 25% of which is in the desacetylated form. Clearance is depressed by probenecid and in renal failure. Little is excreted in the bile. Manifestations of hypersensitivity in patients not known to be allergic to β-lactam antibiotics are common. It is no longer used.

cefacetrile (10206-21-0)Related Product Information

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• [R-[R*,R*-(Z)]]-α-[[(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-1,2,5,7-tetrahydro-7-oxo-4H-Furo[3,4-d][1,3]thiazine-2-acetic Acid
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• 3-ACETOXYMETHYL-7-AMINO-8-OXO-5-THIA-1-AZA-BICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID