Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H16N4O4S2 |
Molecular Weight | 284.356 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O=S1(=O)CCN(CN2CCS(=O)(=O)NC2)CN1
InChI
InChIKey=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
Molecular Formula | C7H16N4O4S2 |
Molecular Weight | 284.356 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Taurolidine [bis(1,1-dioxoperhydro-1,2,4-thiadiazinyl-4)-methane (TRD)], a product derived from the aminosulfoacid taurin, was first described as an anti-bacterial substance. Taurolidine is a small dimeric molecule with
molecular weight 284. It comprises the semiconditional
amino acid taurine. Taurolidine was originally
designed as a broad-spectrum antibiotic. Taurolidine has a broad antimicrobial spectrum of activity that is effective against aerobes and anaerobes, Gram-negative and Gram-posi-tive bacteria as well as yeasts and moulds in vitro. Taurolidine is also effective against methicillin-resistant and vancomycin-resistant bacteria (MRSA, VISA and VRE). It was mainly used in the treatment of patients with peritonis as well as antiendoxic agent in patients with systematic inflammatory response syndrome. It has been shown to be an effective bactericidal agent against both aerobic and
anaerobic bacteria. It is currently licensed for intraperitoneal use in several European countries for the treatment
of peritonitis. The compound appears to be nontoxic and
has an excellent safety record since its initial introduction
over 30 years ago. Taurolidine also possesses antiadherence properties and has been shown in vivo to reduce
the extent and severity of postoperative peritoneal adhesions. It also possesses a strong anti-inflammatory action.
This action appears, at least in part, to arise through its
ability to inactivate endotoxin. Inflammation-induced
tumor development is well described in the literature. Taurolidine’s anti-inflammatory and antiadherence properties prompted an investigation to examine whether it has
a role in antitumor therapy. Taurolidine induces cancer cell death through a variety
of mechanisms. It appears to act through enhancing
apoptosis, inhibiting angiogenesis and tumor adherence,
downregulating proinflammatory cytokine and endotoxin
levels, and stimulating the immune system in response to
surgically induced trauma. Taurolidine is currently in preclinical development for neuroblastoma. In February 23, 2018 the U.S. Food and Drug Administration (FDA) granted orphan drug designation to taurolidine for the treatment of neuroblastoma. Taurolidine is a key component in the Neutrolin®, a novel anti-infective solution for the reduction and prevention of catheter-related infections and thrombosis in patients requiring central venous cathers in end stage renal disease. Neutrolin contains a mix of Taurolidine, Citrate and Heparin. Neutrolin is designed to:
1) Aid in the prevention of Catheter-Related Bloodstream Infections (CRBIs) and
2) Prevent catheter dysfunction (due to blood clotting).
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0007155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20126631 |
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Target ID: map04210 |
PubMed
Title | Date | PubMed |
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Anti-inflammatory effects of taurine derivatives (taurine chloramine, taurine bromamine, and taurolidine) are mediated by different mechanisms. | 2006 |
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Catheter lock solutions: it's time for a change. | 2006 Jul-Sep |
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Pharmacokinetics of taurolidine following repeated intravenous infusions measured by HPLC-ESI-MS/MS of the derivatives taurultame and taurinamide in glioblastoma patients. | 2007 |
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Instillation of taurolidine/heparin after laparotomy reduces intraperitoneal tumour growth in a colon cancer rat model. | 2007 |
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Taurolidine: a novel anti-neoplastic agent induces apoptosis of osteosarcoma cell lines. | 2007 Aug |
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Intra-abdominal use of taurolidine or heparin as alternative products to an antiadhesive barrier (Seprafilm) in adhesion prevention: an experimental study on mice. | 2007 Dec |
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The tumor suppressive reagent taurolidine inhibits growth of malignant melanoma--a mouse model. | 2007 Dec |
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Estimating in vivo airway surface liquid concentration in trials of inhaled antibiotics. | 2007 Fall |
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Influence of intraperitoneal application of taurolidine/heparin on expression of adhesion molecules and colon cancer in rats undergoing laparoscopy. | 2007 Jan |
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Peritoneal instillation of taurolidine or polihexanide modulates intestinal microcirculation in experimental endotoxemia. | 2007 Jul |
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Noninvasive monitoring of myocardial function after surgical and cytostatic therapy in a peritoneal metastasis rat model: assessment with tissue Doppler and non-Doppler 2D strain echocardiography. | 2007 Jul 12 |
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The pharmacokinetics of taurolidine metabolites in healthy volunteers. | 2007 Jun |
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Taurolidine and povidone-iodine induce different types of cell death in malignant pleural mesothelioma. | 2007 Jun |
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Treatment of multiple liver metastasis from gastric carcinoma. | 2007 Jun 21 |
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Is Taurolidine a candidate for treatment of rheumatoid arthritis? | 2007 Mar-Apr |
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Local recurrence model of malignant pleural mesothelioma for investigation of intrapleural treatment. | 2007 May |
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Synergistic effects in apoptosis induction by taurolidine and TRAIL in HCT-15 colon carcinoma cells. | 2007 Nov-Dec |
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Taurolidine induces apoptosis of murine melanoma cells in vitro and in vivo by modulation of the Bcl-2 family proteins. | 2007 Sep 1 |
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Oral administration of taurolidine ameliorates chronic DSS colitis in mice. | 2007 Sep-Oct |
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Leukopoiesis is not affected after intravenous treatment with the novel antineoplastic agent taurolidine. Results of an experimental study in rats. | 2008 |
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Taurolidine and catheter-related bloodstream infection: a systematic review of the literature. | 2008 Aug |
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Using detachment-promoting agents for the prevention of chronic peritoneal dialysis-associated infections. | 2008 Dec |
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TRAIL and Taurolidine induce apoptosis and decrease proliferation in human fibrosarcoma. | 2008 Dec 12 |
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Re: Endophthalmitis: a review of current evaluation and management. | 2008 Feb |
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An evaluation of normal saline and taurolidine on intra-abdominal adhesion formation and peritoneal fibrinolysis. | 2008 Jan |
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The effect of taurolidine on experimental thrombus formation. | 2008 Jan 14 |
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Taurolidine-citrate lock solution (TauroLock) significantly reduces CVAD-associated grampositive infections in pediatric cancer patients. | 2008 Jul 29 |
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Synergistic apoptotic effects of taurolidine and TRAIL on squamous carcinoma cells of the esophagus. | 2008 Jun |
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Novel anti-angiogenic compounds for application in tumor therapy - COP9 signalosome-associated kinases as possible targets. | 2008 May |
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A new haemodialysis catheter-locking agent reduces infections in haemodialysis patients. | 2008 Sep |
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Effects of topical application of taurolidine on second intention healing of experimentally induced wounds in rats. | 2008 Sep |
|
Wound healing is not impaired in rats undergoing perioperative treatment with the antineoplastic agent taurolidine. | 2009 |
|
All-you-can-eat: autophagy in neurodegeneration and neuroprotection. | 2009 Apr 6 |
|
[Spectrum of indications and perioperative management in i. v. port-a-cath explantation--alternative administration of taurolin in case of i. v. port-a-cath infection]. | 2009 Aug |
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Divergent effects of taurolidine as potential anti-neoplastic agent: inhibition of bladder carcinoma cells in vitro and promotion of bladder tumor in vivo. | 2009 Aug |
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Arsenic trioxide exerts synergistic effects with cisplatin on non-small cell lung cancer cells via apoptosis induction. | 2009 Aug 8 |
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Taurolidine in the prevention and therapy of lung metastases. | 2009 Dec |
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Taurolidine and oxidative stress: a rationale for local treatment of mesothelioma. | 2009 Dec |
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The antibacterial substance taurolidine exhibits anti-neoplastic action based on a mixed type of programmed cell death. | 2009 Feb |
|
Microbial inactivation properties of a new antimicrobial/antithrombotic catheter lock solution (citrate/methylene blue/parabens). | 2009 Jun |
|
Taurolidine reduces the tumor stimulating cytokine interleukin-1beta in patients with resectable gastrointestinal cancer: a multicentre prospective randomized trial. | 2009 Mar 23 |
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Principles of the therapy of bone infections in adult extremities : Are there any new developments? | 2009 Oct |
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The evolving role of taurolidine in cancer therapy. | 2010 Apr |
|
Establishment and identification of a rabbit model of peritoneal carcinomatosis from gastric cancer. | 2010 Apr 1 |
|
Taurolidine lock is highly effective in preventing catheter-related bloodstream infections in patients on home parenteral nutrition: a heparin-controlled prospective trial. | 2010 Aug |
|
Multimodal approach for treatment of peritoneal surface malignancies in a tumour-bearing rat model. | 2010 Feb |
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Taurolidine antiadhesive properties on interaction with E. coli; its transformation in biological environment and interaction with bacteria cell wall. | 2010 Jan 28 |
|
A randomized double-blind controlled trial of taurolidine-citrate catheter locks for the prevention of bacteremia in patients treated with hemodialysis. | 2010 Jun |
|
Comparative analysis of cell death induction by Taurolidine in different malignant human cancer cell lines. | 2010 Mar 7 |
|
The antiendotoxin agent taurolidine potentially reduces ischemia/reperfusion injury through its metabolite taurine. | 2010 Sep |
Sample Use Guides
TauroSept® contains a 2% taurolidine solution (0.2 g /10 ml), Sterile Water for Injection, 5% Polyvinylpyrrolidone (PVP) and traces of hydrochloric acid or sodium hydroxide for adjusting the pH value to 7.3. TauroSept® is intended for instillation in central vascular access devices.
TauroSept® is a heat sterilized medical device and comes supplied as a clear, sterile, non-pyrogenic solution. It comes in glass vials that each contains 6 ml or 10 ml solution.
Instructions for use
Always follow the individual catheter manufacturer’s instructions for use carefully. The recommended priming volumes for each individual catheter must be strictly adhered to. Use 10 ml of sterile physiological saline to flush the catheter before instilling TauroSept®. Draw the required amount of TauroSept® from the vial with a sterile syringe and use it to fill the catheter lumen with solution. Allow TauroSept® in the catheter to work for at least 30 minutes or until the next treatment. Aspirate TauroSept®, if possible, and dispose of it as prescribed before using the catheter for the next treatment.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23331343
Curator's Comment: The range of minimum inhibitory concentration (MIC) for anaerobic bacteria is between 0.03– 0.6 mg/ml, for aerobic bacteria between 0.5– 5 mg/ml and for fungi between 0.3–5 mg/ml. http://pharoly.com/documents/monographie_taurosept.pdf
Taurolidine was cytotoxic to osteosarcoma cells and increased the toxicity of doxorubicin and carboplatin in vitro. Apoptosis was greatly induced in cells exposed to 125 uM taurolidine and less so in cells exposed to 250 uM taurolidine.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:19:41 GMT 2023
by
admin
on
Sat Dec 16 17:19:41 GMT 2023
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Record UNII |
8OBZ1M4V3V
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C258
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FDA ORPHAN DRUG |
528816
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FDA ORPHAN DRUG |
500015
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B05CA05
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QB05CA05
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