Antimicrobial; anticancer agent
Taurolidine targets bacterial cell walls and endotoxins through its antimicrobial mechanism. As a formaldehyde carrier, it releases formaldehyde at the site of action, which reacts with bacterial cell wall components and endotoxins. This mechanism avoids cross-resistance with conventional antibiotics. Taurolidine also has antineoplastic activity, inducing apoptosis and decreasing tumor cell proliferation. It has been used with TRAIL to characterize synergistic responses in apoptosis-related signaling proteins.

Taurolidine is a broad-spectrum antimicrobial with activity against both Gram-positive and Gram-negative bacteria, in addition to mycobacteria and certain strains of fungi. The mechanism of action of taurolidine and its active metabolites is non-specific and involves the irreversible binding of its methylol groups to microbial cell walls, resulting in a subsequent loss of cell wall integrity and eventual cell death. In addition, it appears to reduce bacterial adhesion to mammalian cells and neutralize bacterial endo- and exotoxins.
Taurolidine is a synthetic broad-spectrum antimicrobial with antibacterial, antifungal, anticoagulant, and potential antiangiogenic activities. Taurolidine, derived from the amino acid taurine, binds to and neutralizes bacterial exotoxins and endotoxins, or lipopolysaccharides (LPS). Taurolidine binding to LPS prevents bacterial adherence to host epithelial cells, thereby prevents bacterial invasion of uninfected host cells. Although the mechanism underlying its antineoplastic activity has not been fully elucidated, it may be related to this agent's anti-adherence property. In addition, taurolidine also promotes apoptosis by inducing various apoptotic factors and suppresses the production of vascular endothelial growth factor (VEGF), a protein that plays an important role in angiogenesis.
Taurolidine exhibits broad-spectrum in vitro antimicrobial activity against a wide range of gram-positive and gram-negative bacteria, mycobacteria, and some fungi. It acts as a non-antibiotic antimicrobial agent, avoiding cross-resistance. The compound also exhibits antineoplastic activity, inducing apoptosis and decreasing tumor cell proliferation in vitro. These in vitro activities confirm its potential as an antimicrobial and anticancer agent.

Taurolidine is an antimicrobial used for the prevention of catheter-related infections. It is a derivative of the amino acid [taurine]. It was first synthesized in the 1970s and was originally used as a prophylactic against intraperitoneal bacterial infections in patients with peritonitis. In November 2023, a catheter lock solution of taurolidine in combination with [heparin] - marketed as Defencath - received FDA approval under the Limited Population Pathway for Antibacterial and Antifungal Drugs (LPAD pathway) for the prevention of catheter-related bloodstream infections in a limited and specific patient population.
Taurolidine is indicated in combination with [heparin] to reduce the incidence of catheter-related bloodstream infections (CRBSI) in adult patients with kidney failure receiving chronic hemodialysis (HD) through a central venous catheter (CVC).
Taurolidine is used in vivo as an antimicrobial and anti-inflammatory agent. It is primarily used to prevent infections, particularly in catheter-related bloodstream infections. In clinical settings, taurolidine is used as a catheter lock solution. It is also used in the treatment of peritonitis. The compound has been explored for broader applications, including cancer therapy, due to its antineoplastic activity.

In vitro antimicrobial assays for Taurolidine involve measuring its activity against various bacterial and fungal strains. Standard broth microdilution or agar diffusion methods are employed to determine the minimum inhibitory concentration (MIC). Bacterial and fungal cultures are grown in appropriate media, and serial dilutions of Taurolidine are added. After incubation, the MIC is determined. Antineoplastic activity is assessed in cancer cell lines by measuring apoptosis and cell proliferation.

In vitro cellular assays for Taurolidine are conducted in cancer cell lines. Cells are treated with the compound at various concentrations, and apoptosis is assessed by Annexin V staining, caspase activity assays, or PARP cleavage. Cell proliferation is measured using MTT or CellTiter-Glo assays. The compound’s effects on apoptosis-related signaling proteins are assessed by Western blot. These assays characterize the compound’s antineoplastic activity.

In vivo animal experiments with Taurolidine are conducted in models of infection and cancer. In infection models, animals are challenged with pathogenic bacteria, and Taurolidine is administered via injection or as a catheter lock solution. Efficacy endpoints include survival, bacterial load, and infection scores. In cancer models, tumor growth and apoptosis are assessed. These studies define the compound’s in vivo efficacy.

Metabolism / Metabolites
In aqueous solution, taurolidine and taurolactone are in equilibrium, with the latter subsequently metabolized to taurine. Both taurolactone and taurine contribute to the antibacterial activity of taurolidine.
Taurolidine is administered locally as a catheter lock solution or via injection. When used as a catheter lock, systemic absorption is minimal. The compound is metabolized to taurine and formaldehyde, which are excreted. Its half-life and distribution have been characterized in clinical studies. Taurolidine is generally well-tolerated.

Taurolidine is generally well-tolerated when used as a catheter lock solution. Common adverse effects are minimal due to limited systemic absorption. The compound is not associated with significant systemic toxicity. It is contraindicated in patients with known hypersensitivity. The compound’s safety profile is well-established from clinical use.

[1]. Taurolidine, an antiseptic for the prevention of central venous catheter-related infections. Rev Chilena Infectol. 2019 Aug;36(4):414-420.

[2]. Treatment of glioblastoma with intravenous taurolidine. First clinical experience. Anticancer Res. 2004 Mar-Apr;24(2C):1143-7.

Tauroride belongs to the thiadiazine class of compounds, with the structure 1,2,4-thiadiazine-1,1-dioxide, substituted at position 4 with (1,1-dioxide-1,2,4-thiadiazine-4-yl)methyl. It is a broad-spectrum disinfectant, commonly used as a locking solution for patients with long-term indwelling central venous catheters to prevent catheter-related bloodstream infections. It possesses multiple effects including antibacterial, anti-inflammatory, antifungal, disinfectant, and antitumor properties. It is a thiadiazine sulfone compound. Tauroride is an antibacterial agent used to prevent catheter-related infections. It is a derivative of the amino acid taurine. It was first synthesized in the 1970s, initially for the prevention of intra-abdominal bacterial infections in patients with peritonitis. In November 2023, a catheter locking solution containing tauroride and heparin (trade name Defencath) received approval from the U.S. Food and Drug Administration (FDA) for the prevention of catheter-related bloodstream infections in a specific patient population. This approval pathway is the Limited Population Approval (LPAD) pathway for antibacterial and antifungal drugs. Tauroride is a synthetic broad-spectrum antibacterial agent with antibacterial, antifungal, anticoagulant, and potential anti-angiogenic activities. Tauroride is derived from the amino acid taurine, which can bind to and neutralize bacterial exotoxins and endotoxins, namely lipopolysaccharide (LPS). The binding of tauroride to LPS prevents bacteria from adhering to host epithelial cells, thereby preventing bacterial invasion of uninfected host cells. Although the mechanism of its antitumor activity is not fully elucidated, it may be related to its anti-adhesion properties. Furthermore, tauroride can promote apoptosis by inducing various apoptosis factors and inhibit the production of vascular endothelial growth factor (VEGF), a protein that plays an important role in angiogenesis. Drug Indications Tauroride, used in combination with heparin, is used to reduce the incidence of catheter-related bloodstream infections (CRBSI) in adult patients with renal failure undergoing chronic hemodialysis (HD) via central venous catheters (CVCs).

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Mechanism of Action
Tauroropyridine is a broad-spectrum antibacterial drug active against Gram-positive and Gram-negative bacteria, mycobacteria, and certain fungal strains. The mechanism of action of tauroropyridine and its active metabolites is non-specific; its hydroxymethyl group irreversibly binds to the cell wall of microorganisms, leading to loss of cell wall integrity and ultimately cell death. Furthermore, it appears to reduce bacterial adhesion to mammalian cells and neutralize bacterial endotoxins and exotoxins.

Taurolidine is a synthetic, broad-spectrum antimicrobial agent derived from taurine. It is also known as Taurolin and Tauroline. The compound is used for the prophylaxis of catheter-related infections and as a catheter lock solution. It also has antineoplastic activity, inducing apoptosis and decreasing tumor cell proliferation. Taurolidine has been investigated for the prevention of central venous catheter infections and for cancer therapy. Its unique mechanism avoids cross-resistance with conventional antibiotics.

C7H16N4O4S2

284.3563

284.061

C, 29.57; H, 5.67; N, 19.70; O, 22.51; S, 22.55

19388-87-5

19388-87-5; 1333382-80-1 (citrate); 352464-86-9 (nitrate)

29566

Solid powder

1.5±0.1 g/cm3

471.2±55.0 °C at 760 mmHg

156ºC

238.8±31.5 °C

0.0±1.2 mmHg at 25°C

1.564

-2.55

2

8

2

17

419

0

S1(C([H])([H])C([H])([H])N(C([H])([H])N1[H])C([H])([H])N1C([H])([H])N([H])S(C([H])([H])C1([H])[H])(=O)=O)(=O)=O

AJKIRUJIDFJUKJ-UHFFFAOYSA-N

InChI=1S/C7H16N4O4S2/c12-16(13)3-1-10(5-8-16)7-11-2-4-17(14,15)9-6-11/h8-9H,1-7H2

4,4'-methylenebis(1,2,4-thiadiazinane 1,1-dioxide)

Taurolidine; TAUROLIDINE; 19388-87-5; Taurolin; Tauroline; Taurolidina; heparin (Defencath)

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~62.5 mg/mL (~219.80 mM)

Solubility in Formulation 1: ≥ 2.08 mg/mL (7.31 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.08 mg/mL (7.31 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (7.31 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)