4697-14-7 Usage
Description
Ticarcillin disodium salt is a semisynthetic β-lactam antibiotic derived from the carboxypenicillin class. It is characterized by its white solid appearance and is known for its activity against various gram-negative bacteria, including Pseudomonas aeruginosa, E. coli, P. mirabilis, P. rettgeri, and K. aerogenes. Ticarcillin disodium salt is commonly administered topically and is used in the treatment of a wide range of bacterial infections.
Uses
1. Used in Pharmaceutical Industry:
Ticarcillin disodium salt is used as an injectable antibiotic for the treatment of infections caused by gram-negative bacteria, particularly Pseudomonas aeruginosa. Its effectiveness in combating these infections makes it a valuable asset in the pharmaceutical industry.
2. Used as a Coccidiostat:
In the veterinary industry, Ticarcillin disodium salt is used as a coccidiostat to prevent and treat coccidiosis, a disease caused by the protozoan parasite Eimeria. Its application in this field helps maintain the health of livestock and contributes to the overall productivity of the industry.
3. Used in Ophthalmology:
Ticarcillin disodium salt is used as a topical treatment in ophthalmology to reduce the colony count of P. aeruginosa in the eyes of rabbits. This application highlights its potential in treating bacterial eye infections and promoting eye health.
Originator
Ticar,Beecham,US,1976
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
Check Digit Verification of cas no
The CAS Registry Mumber 4697-14-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,6,9 and 7 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 4697-14:
(6*4)+(5*6)+(4*9)+(3*7)+(2*1)+(1*4)=117
117 % 10 = 7
So 4697-14-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H16N2O6S2.2Na/c1-15(2)9(14(22)23)17-11(19)8(12(17)25-15)16-10(18)7(13(20)21)6-3-4-24-5-6;;/h3-5,7-9,12H,1-2H3,(H,16,18)(H,20,21)(H,22,23);;/q;2*+1/p-2/t7?,8-,9+,12-;;/m1../s1
