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Ticarcillin disodium salt, CAS 4697-14-7, molecular formula C15H17N2NaO6S2, is a semi synthetic penicillin antibiotic. Usually white to light yellow to light orange crystalline powder, it is a complex organic compound with multiple functional groups in its structure, such as carboxyl, thienyl, amino, etc. Easy to dissolve in water, the aqueous solution is relatively stable; The solubility in H2O can reach 50mg/mL, and the resulting clear solution has a pH value of 6.0-8.0. The property of being easily soluble in water facilitates its dissolution and absorption in the body, thereby improving the bioavailability of drugs.
Water solutions are relatively stable, but acidic solutions are relatively unstable, so attention should be paid to avoiding acidic environments during storage and use. During the heating process, a decomposition reaction occurs, and the specific decomposition temperature and decomposition products depend on the heating conditions and material purity.
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Chemical Formula |
C15H14N2O6S22- |
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Exact Mass |
382.03 |
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Molecular Weight |
382.41 |
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m/z |
191.02 (100.0%), 191.52 (16.2%), 192.01 (9.0%), 191.51 (1.6%), 192.51 (1.5%), 192.02 (1.2%), 192.02 (1.2%) |
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Elemental Analysis |
C, 47.11; H, 3.69; N, 7.33; O, 25.10; S, 16.77 |
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Core Clinical Applications
Ticarcillin disodium salt is a commonly used agent for treating severe bacterial infections. With broad-spectrum antibacterial activity, targeted action and stable therapeutic effects, it is widely deployed for moderate-to-severe and complicated bacterial infections. It can be administered alone or combined with β-lactamase inhibitors such as clavulanate potassium to enhance bactericidal activity against resistant strains, meeting infection treatment needs across multiple clinical departments.
Treatment of Respiratory Tract Infections
Respiratory bacterial infections represent one of the primary indications for the producr. The drug penetrates respiratory mucosal tissue and achieves effective concentrations at lesion sites including airways and alveoli, delivering reliable efficacy against acute and chronic respiratory infections caused by susceptible pathogens. Clinically, it treats acute bronchitis, acute exacerbations of chronic bronchitis, community-acquired pneumonia, hospital-acquired pneumonia, and bronchiectasis complicated by infection, with causative pathogens including Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa, and Escherichia coli.
The product offers particular advantages for hospital-acquired pulmonary infections. Pathogens isolated from nosocomial infections often carry resistance, and Pseudomonas aeruginosa is a key pathogen. The product is among the few penicillins retaining high activity against Pseudomonas aeruginosa. It effectively controls cough, sputum production, high fever, dyspnea and other manifestations of severe pulmonary infection and prevents spread into deep lung tissue and systemic circulation. In immunocompromised populations such as the elderly, bedridden patients, and patients receiving chemotherapy or radiotherapy, the agent rapidly suppresses severe respiratory infection and reduces the risk of serious complications including respiratory failure, making it a first-line therapy for severe respiratory infections.
Treatment of Urogenital Tract Infections
Most urogenital infections are caused by invasive Gram-negative bacteria; these infections are prone to recurrence and progression to complicated disease. The product exhibits high susceptibility against common urinary pathogens and serves as an important clinical agent for diverse urinary tract infections. Indications include uncomplicated urinary tract infection, complicated urinary tract infection, pyelonephritis, cystitis, prostatitis and pelvic infection. It effectively eradicates major urinary pathogens such as Escherichia coli, Proteus mirabilis, Enterobacter cloacae and Pseudomonas aeruginosa.
Compared with conventional urinary antibiotics, the product performs better in complicated infections caused by resistant strains. For urinary calculi with superimposed infection, postoperative ascending urinary tract infection, and recurrent chronic urinary tract infection, it rapidly resolves inflammation, relieves dysuria, frequency, urgency, lumbago and fever, eliminates pathogens within lesions, and lowers relapse rates. In addition, the drug accumulates to high concentrations in urinary tissues, exhibits stable metabolism, and causes minimal irritation to normal renal tissue. At standard doses, it can be safely used for moderate-to-severe urinary tract infections in adults and children, supporting broad clinical applicability.
Treatment of Intra-Abdominal and Soft-Tissue Infections
Intra-abdominal infections are frequently polymicrobial, involving both aerobes and anaerobes, and carry rapid progression and high mortality, demanding antibiotics with an extensive spectrum. The product possesses dual activity against aerobic and anaerobic bacteria and covers most pathogens in intra-abdominal infections. It is widely used for severe intra-abdominal conditions including peritonitis, intra-abdominal abscess, cholecystitis, and perforated appendicitis with infection. For postoperative complications such as surgical-site abdominal infection and infected ascites, it rapidly controls local inflammation, blocks infection dissemination, reduces postoperative infection-related mortality, and facilitates recovery.
In skin and soft-tissue infections, the product targets moderate-to-severe disease including traumatic wound infection, burn wound infection, cellulitis, and deep soft-tissue abscess. Such infections are often driven by resistant organisms such as Staphylococcus aureus, Pseudomonas aeruginosa, and Klebsiella species, against which conventional antibiotics show limited efficacy. The product penetrates deep soft tissue to reach infected lesions, kills pathogens, reduces inflammatory exudate from wounds, and prevents severe sequelae such as tissue necrosis and sepsis. It is especially suitable for anti-infective management after extensive burns and major trauma.
Applications in Biological Research
Beyond clinical use, ticarcillin disodium salt functions as an important research reagent in molecular biology, plant genetic engineering, and cell culture due to precise bacteriostatic targeting and low cytotoxicity. It is widely employed for experimental contamination control, material purification, and system stabilization as a routine functional antibiotic in laboratories.
Bacteriostatic Control in Plant Transgenic Experiments
In Agrobacterium-mediated plant transformation, Agrobacterium tumefaciens delivers foreign genes into plant cells, yet residual bacteria continue to proliferate after transformation, interfering with callus differentiation and seedling development and causing experimental failure. The product exerts specific potent bactericidal activity against Agrobacterium while displaying very low toxicity toward plant cells and callus, without inhibiting cell division and differentiation. It is therefore the preferred bacteriostatic reagent for plant transgenic work.
During the co-cultivation phase after Agrobacterium infection of explants, addition of the product at an appropriate concentration completely eliminates residual bacteria on and inside explants, preventing browning and contamination from overgrowth. It does not interfere with integration and expression of transgenes and substantially improves recovery of transgenic plant lines. It is now routinely used in transgenic breeding for rice, Arabidopsis thaliana, tobacco, fruits and vegetables, and other plant species.
Contamination Control in Cell Culture Systems
Animal and microbial cell culture requires stringent asepsis; bacterial contamination is a leading source of experimental artifacts. The product has a broad spectrum, suppressing common Gram-negative and selected Gram-positive contaminants in culture systems. Compared with routine agents such as penicillin and streptomycin, it is associated with lower resistance emergence and better cellular compatibility.
In high-precision work including stem-cell culture, tumor-cell culture, and primary-cell isolation, supplemented the product helps maintain stable aseptic cultures and prevents microbial overgrowth from compromising cell viability and data integrity. Importantly, it does not alter cellular biological properties, proliferation kinetics or gene-expression profiles, maximizing reliability of cell-based assays. It serves as a core reagent for contamination control in biological laboratories.
Method 1: Chemical synthesis method
The chemical synthesis of ticarcillin disodium salt is a complex and intricate process involving multiple steps and chemical reactions.
Synthetic raw materials and intermediates
The synthetic raw materials of ticarcillin disodium mainly include 6-aminopenicillanic acid (6-APA), 3-thiophene malonic acid or its derivatives. Among them, 3-thiophene malonic acid is an important intermediate, and its synthesis process is also relatively complex.
Synthesis steps
1. Synthesis of 3-thiophene malonic acid
3-thiophene malonic acid is a key intermediate for the synthesis of ticarcillin disodium. The synthesis process usually includes the following steps:
(1) Addition reaction of acetylene and chloroacetyl chloride:
Firstly, acetylene and chloroacetyl chloride undergo an addition reaction under the action of a catalyst, producing (E) -1,4-dichloro-3-buten-2-one.
(2) Cronenberg reaction:
Next, (E)-1, 4-Dichloro-3-buten-2-one undergoes the Krebs reaction to generate the corresponding ketone acid.
(3) Hydrolysis and cyclization reaction:
Finally, the ketone acid undergoes hydrolysis and cyclization reaction to obtain 3-thiophene malonic acid.
2. Synthesis of ticarcillin monosodium salt
After obtaining 3-thiophene malonic acid, ticarcillin monosodium salt can be further synthesized. The specific steps are as follows:
(1) Activation of 3-thiophene malonic acid:
Firstly, 3-thiophene malonic acid is activated by esterification reaction to convert it into the corresponding ester compound for subsequent chlorination reaction.
(2) Chlorination reaction:
Activated 3-thiophene malonate reacts with chlorinating agents such as dichlorosulfoxide to generate the corresponding acyl chloride.
(3) Condensation reaction:
Next, the generated acyl chloride is subjected to condensation reaction with 6-APA. This step is usually carried out in the presence of appropriate solvents and catalysts to generate the acid salt of ticarcillin.
(4) Salt formation reaction:
Finally, the acid salt of ticarcillin is reacted with a base such as sodium hydroxide to form a salt, resulting in the formation of ticarcillin monosodium salt.
3. Synthesis of the product
After obtaining ticarcillin monosodium salt, it can be further processed to obtain ticarillin disodium salt. The specific steps are as follows:
(1) Preparation of solution:Firstly, dissolve ticarcillin monosodium salt in a suitable solvent, such as water or organic solvent.
(2) Adjust pH value:Next, adjust the pH value of the solution by adding acid or base for subsequent salt formation reactions.
(3) Salting and refining:Under appropriate temperature and stirring conditions, salt forming agents (such as sodium bicarbonate, sodium acetate, etc.) are added to the solution to convert ticarcillin monosodium salt to ticarillin disodium salt.
Then, the product is refined through steps such as filtration, washing, and drying to obtain high-purity ticarillin disodium salt.The chemical synthesis of ticarcillin disodium is a complex and intricate process involving multiple steps and chemical reactions. By strictly controlling reaction conditions, selecting appropriate catalysts and solvents, and purifying the product, high-purity and stable quality ticarillin disodium salt can be obtained. This synthesis method has broad application prospects and important clinical significance.
Method 2: Fermentation method
The fermentation production of ticarcillin disodium salt is a complex biochemical process that combines microbial metabolic activity with specific chemical transformation steps. The following is a detailed explanation of the production steps:
Preparation before fermentation
The starting point of fermentation production is to select suitable microbial strains. These strains typically have the ability to produce penicillin compounds and have been screened and optimized to increase the production of ticarcillin.
Before formal fermentation, it is necessary to cultivate and domesticate the bacterial strains to adapt to the environmental conditions during the fermentation process and achieve optimal growth and metabolic status.
Fermentation medium is a mixture of nutrients required for microbial growth and metabolism. For production, fermentation media typically contain carbon sources (such as glucose, sucrose, etc.), nitrogen sources (such as amino acids, urea, etc.), inorganic salts (such as phosphates, magnesium salts, etc.), and growth factors.
The preparation of culture medium requires precise control of the proportions and concentrations of various components to ensure the normal growth and metabolism of microorganisms.
Fermentation equipment is a key device in the production process, including fermentation tanks, mixers, cooling systems, ventilation systems, etc.
Before fermentation, it is necessary to thoroughly clean and disinfect the equipment to prevent bacterial contamination. At the same time, it is necessary to check the operation status of the equipment to ensure that it can work properly.
Fermentation process
(1) Vaccination and cultivation
Inoculate the cultured and domesticated strains into the fermentation medium to begin the fermentation process.
In the early stages of fermentation, it is necessary to control appropriate conditions such as temperature, pH value, and ventilation to promote the growth and metabolism of microorganisms.
(2) Accumulation of metabolites
As microorganisms grow and metabolize, ticarcillin or its precursor substances begin to accumulate in the fermentation broth.
At this point, it is necessary to closely monitor the concentration and proportion of various metabolites in the fermentation broth, as well as the growth status of microorganisms.
(3) Adjustment of fermentation conditions
According to the monitoring results, adjust the fermentation conditions in a timely manner, such as temperature, pH value, aeration rate, stirring speed, etc., to optimize the yield and quality of Tigasilin.
For example, when the production of ticarcillin begins to decrease, the ventilation rate and stirring speed can be appropriately increased to promote microbial metabolic activity.
Processing after fermentation
(1) Collection and treatment of fermentation broth
When the fermentation process reaches the predetermined time or the production of ticarcillin reaches its maximum value, stop fermentation and collect the fermentation broth.
The fermentation broth needs to be filtered, centrifuged, and other steps to remove microbial cells and solid impurities, resulting in a clear fermentation broth.
(2) Extraction and Purification
The ticarcillin or its precursor substances in the fermentation broth need to be separated and purified through appropriate extraction and purification steps.
The extraction steps usually include solvent extraction, ion exchange, membrane separation, etc. The purification steps include crystallization, recrystallization, chromatographic separation, etc.
The purpose of these steps is to remove impurities and by-products from the fermentation broth and improve the purity of ticarcillin.
(3) Salt formation and drying
After extraction and purification, ticarcillin or its precursor substances need to undergo salt formation reaction with appropriate bases to obtain the substance.
The salt formation reaction needs to be carried out under appropriate temperature and pH conditions to ensure stability and yield.
Finally, it will undergo drying treatment to remove moisture and volatile impurities, resulting in the final product.
In summary, the production of the product is a complex and delicate process that requires strict control of the conditions and operational steps at each stage. Through continuous optimization and improvement, the production and quality of ticarcillin disodium can be increased, meeting market demand and promoting the development of the pharmaceutical industry.
FAQ
1. Why does USP set the ticarcillin content at "80.0%–94.0%" for the bulk salt, but "90.0%–115.0%" for the finished injection? Isn't the salt supposed to be purer?
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This is not about purity, but about calculation basis. For the bulk salt (80–94%), the content is calculated on the anhydrous basis and reflects the intrinsic drug substance specification. For the finished injection (90–115%), it is calculated as is (label claim), allowing for overfill and excipient dilution. The salt is never 100% due to sodium content, residual solvents, and water; USP 29 requires potency ≥800 µg/mg (~84% at 952 µg/mg theoretical).
2. Its major degradation product has its own UNII (0A6CP1X10G). What is this compound and why does it matter for powder handling?
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It is Ticarcilloic Acid – the penicilloic acid formed by hydrolysis of the β-lactam ring . This is the primary degradation pathway. Its existence explains why ticarcillin powder must be stored in tight containers and protected from moisture. USP limits water to ≤6.0% for this exact reason; exposure to humidity triggers ring opening, inactivating the drug.
3. The stability data shows a paradox: it loses 7% in 3 days at 23°C but 14% in 5 days. Why is the degradation rate nonlinear?
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This is autocatalytic hydrolysis. The initial breakdown products (ticarcilloic acid) acidify the microenvironment, accelerating further degradation. The "7% at 3d → 14% at 5d" jump reflects this positive feedback. At 4°C, the loss stays <7% for 21 days, then jumps to 12% at 30 days – same mechanism, simply slowed by cold. This is why "beyond-use" dates are not linear extrapolations.
4. How can ticarcillin powder be simultaneously "feeble inducer" of β-lactamases yet highly susceptible to them? Isn't that contradictory?
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Induction and hydrolysis are distinct properties. Ticarcillin is a poor inducer – it weakly stimulates bacteria to produce more β-lactamase. But once the enzyme is already present (whether constitutive or induced by other drugs), ticarcillin is excellently hydrolyzed by many class I β-lactamases. This is why adding clavulanate (a suicide inhibitor) rescues its activity, and why clavulanate itself can paradoxically antagonize ticarcillin in some Enterobacter strains by inducing more enzyme than it inhibits.
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