| Identification | More | [Name]
Ticarcillin disodium salt | [CAS]
4697-14-7 | [Synonyms]
(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
(2S,5S,6R)-6-[[(2R)-CARBOXY-3-THIENYLACETYL]AMINO]-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3,2,0]HEPT
TICAR
TICARCILLIN DISODIUM
TICARCILLIN DISODIUM SALT
TICARCILLIN SODIUM
TIMENTIN
3-thiophenemalonamicacid,n-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicylo(3
ticarpen
TICARCILLIN IMPURITY A(2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-[[(THIOPHEN-3-YL)ACETYL]-AMINO]-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID (DECARBOXYTICARCILLIN) EPT(CRM STANDARD)
TicarcillinDisodiumC15H14N2Na2O6S2
(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
Ticarcillin sodium
Timentin sodium
Ticarcillin disodium salt/Potassium clavulanate mixture (15:1)
CSL Ticillin , Tarcil
SmithKline Beecham Sodium Ticarcillin
[2S-[2α，5α，6β(S^<*>^)]]-6-[(Carboxy-3-thienylacetyl)amino]-3，3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid disodium salt
Aerugipen
Neoanabactyl | [EINECS(EC#)]
628-059-3 | [Molecular Formula]
C15H14N2Na2O6S2 | [MDL Number]
MFCD07787410 | [Molecular Weight]
428.39 | [MOL File]
4697-14-7.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R42:May cause sensitization by inhalation.
R43:May cause sensitization by skin contact.
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
2
| [RTECS ]
XM9410000
| [HS Code ]
2941100000 |
| Hazard Information | Back Directory | [Description]
Ticarcillin is a semisynthetic β-lactam antibiotic.1,2 It is active against P. aeruginosa, E. coli, P. mirabilis, P. rettgeri, and K. aerogenes (MICs = 4-125 μg/ml).2 Topical administration of ticarcillin (2.5 mg per eye) reduces P. aeruginosa colony count in rabbit eye.1 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]
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-nega
tive bacteria, particularly Pseudomonas aeruginosa. | [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 | [storage]
4°C, protect from light |
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