Ticarcillin disodium salt

Bezeichnung:Ticarcillin disodium salt

CAS-Nr4697-14-7

Englisch Name:Ticarcillin disodium salt

CBNumberCB3147339

SummenformelC15H17N2NaO6S2

Molgewicht408.42

MOL-Datei4697-14-7.mol

Ticarcillin disodium salt physikalisch-chemischer Eigenschaften

Schmelzpunkt	>173°C (dec.)
storage temp.	2-8°C
Löslichkeit	H2O: soluble50mg/mL
Aggregatzustand	powder
Farbe	white to light yellow
Merck	13,9505
Stabilität	Moisture sensitive
InChIKey	ZBBCUBMBMZNEME-QBGWIPKPSA-L
CAS Datenbank	4697-14-7(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	36/37/38-42-43-42/43
S-Sätze:	26-36/37
WGK Germany	2
RTECS-Nr.	XM9410000
HS Code	2941100000

Gefahreninformationscode (GHS)

Ticarcillin disodium salt Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R42:Sensibilisierung durch Einatmen möglich.
R43:Sensibilisierung durch Hautkontakt möglich.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Beschreibung
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.
Chemische Eigenschaften
Ticarcillin disodium salt is White Solid
Originator
Ticar,Beecham,US,1976
Verwenden
coccidiostat
Verwenden
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
Allgemeine Beschreibung
Ticarcillin was synthesized by Beecham Research Laboratories in 1971. The phenyl residue of carbenicillin was replaced by the 3-thienyl moiety. Ticarcillin shows almost the same activity as carbenicillin against gram-positive bacteria and a twofold higher activity against gram-negative bacteria. Its in vivo activity against Pseudomonas aeruginosa infections in mice is fourfold higher than that of sulbenicillin. Ticarcillin is used to treat sepsis, urinary tract infections, and serious Pseudomonas aeruginosa, Escherichia coli, Proteus, and Enterobacter infections in leukemic and other cancer patients.

Ticarcillin disodium salt Upstream-Materialien And Downstream Produkte

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