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| Product Name: | Ticarcillin disodium salt | | Synonyms: | (2S,5S,6R)-6-[[(2R)-CARBOXY-3-THIENYLACETYL]AMINO]-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3,2,0]HEPT;(2S,5R,6R)-6-[[(2R)-CARBOXY-3-THIENYLACETYL]AMINO]-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID DISODIUM SALT;TICAR;TICARCILLIN DISODIUM;Ticarcillin Sodium/Potassium Clavulanate (15:1);Disodium (2S,5R,6R)-6-[[(2RS)-2-carboxylato-2-(thiophen-3-yl)acetyl] amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;Ticarcillin disodium salt, Antibiotic for Culture Media Use Only;Ticarcillin (sodium salt) | | CAS: | 4697-14-7 | | MF: | C15H17N2NaO6S2 | | MW: | 408.42 | | EINECS: | 628-059-3 | | Product Categories: | BAYCOX;antibiotic;4697-14-7 | | Mol File: | 4697-14-7.mol |  |
| | Ticarcillin disodium salt Chemical Properties |
| Melting point | >173°C (dec.) | | storage temp. | 2-8°C | | solubility | H2O: soluble50mg/mL | | form | powder | | color | white to light yellow | | Merck | 13,9505 | | Stability: | Moisture sensitive | | InChIKey | ZBBCUBMBMZNEME-QBGWIPKPSA-L | | CAS DataBase Reference | 4697-14-7(CAS DataBase Reference) |
| | Ticarcillin disodium salt Usage And Synthesis |
| Brand Name(s) in US | Ticar, Ticillin
| | Description | 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. | | Chemical Properties | Ticarcillin disodium salt is White Solid
| | Originator | Ticar,Beecham,US,1976 | | Uses | 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. | | Uses | coccidiostat | | Uses | 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. | | 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 |
| | Ticarcillin disodium salt Preparation Products And Raw materials |
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