4697-14-7

Ticarcillin is a semisynthetic β-lactam antibiotic. It is active against P. aeruginosa, E. coli, P. mirabilis, P. rettgeri, and K. aerogenes (MICs = 4-125 μg/ml). Topical administration of ticarcillin (2.5 mg per eye) reduces P. aeruginosa colony count in rabbit eye. Formulations containing ticarcillin have been used in the treatment of a variety of bacterial infections.

Ticarcillin disodium salt is White Solid

Ticar,Beecham,US,1976

coccidiostat

The disodium salt of Ticarcillin, a carboxypenicillin belonging to the beta-lactam class of antibiotics. Ticarcillin is an injectable antibiotic used in the treatment of infections caused by gram-nega tive bacteria, particularly Pseudomonas aeruginosa.

The disodium salt of Ticarcillin, a carboxypenicillin belonging to the beta-lactam class of antibiotics. Ticarcillin is an injectable antibiotic used in the treatment of infections caused by gram-negative bacteria, particularly Pseudomonas aeruginosa.

ChEBI: Ticarcillin disodium is an organic sodium salt. It contains a ticarcillin(2-).

A mixture of monobenzyl-3-thienylmalonate (1.38 g, 5 mmol) and thionyl chloride (2.5 ml) was warmed at 50°C to 55°C for 1 hour, then at 60°C to 65°C for 10 minutes. The excess of thionyl chloride was removed in vacuo at not more than 30°C, the last traces being removed by codistillation with dry benzene (1 ml) under high vacuum, leaving monobenzyl3-thienylmalonyl chloride as a yellow oil.
The acid chloride obtained as described above was dissolved in dry acetone (10 ml) and added in a steady stream to a stirred solution of 6- aminopenicillanic acid (1.08 g, 5 mmol) in a mixture of N sodium bicarbonate (15 ml) and acetone (5 ml). After the initial reaction the reaction mixture was stirred at room temperature for 45 minutes, then washed with ether (3 x 25 ml). Acidification of the aqueous solution with N hydrochloric acid (11 ml) to pH 2 and extraction with ether (3 x 15 ml) gave an ethereal extract which was decolorized with a mixture of activated charcoal and magnesium sulfate for 5 minutes.
The resulting pale yellow ethereal solution was shaken with sufficient N sodium bicarbonate (4 ml) to give an aqueous extract of pH 7 to 7.5. This extract was concentrated to syrup at low temperature and pressure, then isopropanol was added with stirring until the mixture contained about 10% water.
Crystallization was initiated, and completed at about 0°C overnight, to give the sodium salt of α-(benzyloxycarbonyl)-3-thienylmethylpenicillin as white crystals in 50% weight yield. This product was estimated by colorimetric assay with hydroxylamine to contain 91% of the anhydrous sodium salt. A solution of the sodium salt of α-(benzyloxycarbonyl)-3- thienylmethylpenicillin (2.13 g, 4.3 mmol) in water (30 ml) was added to a suspension of 5% palladium on calcium carbonate (10.65 g) in water (32 ml) which had been prehydrogenated for 1 hour.
The mixture was then hydrogenated at just above atmospheric pressure for 1 1/2 hours and filtered through a Dicalite bed. The clear filtrate was evaporated at low temperature and pressure, and the residue dried in vacuo over phosphorus pentoxide, to give 1.64 g of the salt of α-(3- thienyl)methylpenicillin as a white solid. Colorimetric assay with hydroxylamine showed this salt to contain 94% of the anhydrous penicillin. Paper chromatography showed complete reduction of the benzyl group.

Antibiotic

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