| Identification | Back Directory | [Name]
cefacetrile | [CAS]
10206-21-0 | [Synonyms]
Cefacetrilo
cefacetrile
CEPHACETRILE
Cefacetrilum
cefacetrile USP/EP/BP
Cephacetrile,Cefacetrile
Cefacetrilum [inn-latin]
Cefacetrilo [inn-spanish]
7-Cyanacetylamino-cephalosporansaeure
Cephacetrile (base and/or unspecified salts)
(7R)-3-[(Acetyloxy)methyl]-7-[(cyanoacetyl)amino]cepham-3-ene-4-carboxylic acid
(6R,7R)-3-Acetoxymethyl-7-(2-cyanacetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure
7-(2-Cyanacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carboxylat acetat (ester)
(6R,7R)-7-(2-Cyanoacetylamino)-3-(acetoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]octan-2-ene-2-carboxylic acid
(6R,7R)-3-[(Acetyloxy)Methyl]-7-[(2-cyanoacetyl)aMino]-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
7-(2-CyanoacetaMido)-3-(hydroxyMethyl)-8-oxo-5-thia-
-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Acetate (Ester)
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[(2-cyanoacetyl)amino]-8-oxo-, (6R,7R)- | [EINECS(EC#)]
233-508-8 | [Molecular Formula]
C13H13N3O6S | [MDL Number]
MFCD00865099 | [MOL File]
10206-21-0.mol | [Molecular Weight]
339.327 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
pKa 1.97 (Uncertain) | [color ]
White to Pale Beige | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [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. | [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. | [storage]
-20°C |
|
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Energy Chemical
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021-58432009 400-005-6266 |
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http://www.energy-chemical.com |
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