Ticarcillin sodium Property

storage temp. 

-20°C

CAS DataBase Reference

74682-62-5(CAS DataBase Reference)

Safety

HS Code 

2941106000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P285In case of inadequate ventilation wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P341IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.

P321Specific treatment (see … on this label).

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

Ticarcillin sodium Chemical Properties,Usage,Production

Originator

Ticar,Beecham,US,1976

Uses

Ticar (Glaxo-SmithKline).

Definition

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

Manufacturing Process

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.

Therapeutic Function

Antibiotic

Clinical Use

Ticarcillin disodium, α-carboxy-3-thienylpenicillin (Ticar),is an isostere of carbenicillin in which the phenyl group is replacedby a thienyl group. This semisynthetic penicillinderivative, like carbenicillin, is unstable in acid and, therefore,must be administered parenterally. It is similar tocarbenicillin in antibacterial spectrum and pharmacokineticproperties. Two advantages for ticarcillin are claimed:(a) slightly better pharmacokinetic properties, includinghigher serum levels and a longer duration of action; and(b) greater in vitro potency against several species of Gramnegativebacilli, most notably P. aeruginosa and Bacteroidesfragilis. These advantages can be crucial in the treatment ofserious infections requiring high-dose therapy.