Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H16N4O4S2.C6H8O7 |
Molecular Weight | 476.48 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O.O=S1(=O)CCN(CN2CCS(=O)(=O)NC2)CN1
InChI
InChIKey=RMTOBKFGSODIEJ-UHFFFAOYSA-N
InChI=1S/C7H16N4O4S2.C6H8O7/c12-16(13)3-1-10(5-8-16)7-11-2-4-17(14,15)9-6-11;7-3(8)1-6(13,5(11)12)2-4(9)10/h8-9H,1-7H2;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
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 |
Molecular Formula | C6H8O7 |
Molecular Weight | 192.1235 |
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 |
|||
Target ID: map04210 |
PubMed
Title | Date | PubMed |
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Two years' experience with Dialock and CLS (a new antimicrobial lock solution). | 2001 |
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[Experimental study of antiseptic (tauroline, taurolidine) and antibiotic (sulmycin implant) drugs in vascular prosthesis infections in a standardized infection model]. | 2001 May |
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Taurolidine: cytotoxic and mechanistic evaluation of a novel antineoplastic agent. | 2001 Sep 15 |
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Effects of taurolidine and octreotide on port site and liver metastasis after laparoscopy in an animal model of pancreatic cancer. | 2002 |
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Taurolidine attenuates the hemodynamic and respiratory changes associated with endotoxemia. | 2002 Apr |
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A randomized double-blinded placebo-controlled crossover trial of nebulized taurolidine in adult cystic fibrosis patients infected with Burkholderia cepacia. | 2002 Spring |
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Intravitreal taurolidine against experimental Staphylococcus epidermidis endophthalmitis in rabbits. | 2004 Apr |
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Treatment of glioblastoma with intravenous taurolidine. First clinical experience. | 2004 Mar-Apr |
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The tumor-suppressive reagent taurolidine is an inhibitor of protein biosynthesis. | 2004 Nov 1 |
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Comment on 'in vivo effects of fluoroquinolones on rabbit corneas'. | 2005 Feb |
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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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Prevention of disease progression in a patient with a gastric cancer-re-recurrence. Outcome after intravenous treatment with the novel antineoplastic agent taurolidine. Report of a case. | 2006 Jun 24 |
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Instillation of taurolidine/heparin after laparotomy reduces intraperitoneal tumour growth in a colon cancer rat model. | 2007 |
|
Taurolidine and povidone-iodine induce different types of cell death in malignant pleural mesothelioma. | 2007 Jun |
|
Local recurrence model of malignant pleural mesothelioma for investigation of intrapleural treatment. | 2007 May |
|
TRAIL and Taurolidine induce apoptosis and decrease proliferation in human fibrosarcoma. | 2008 Dec 12 |
|
Taurolidine-citrate lock solution (TauroLock) significantly reduces CVAD-associated grampositive infections in pediatric cancer patients. | 2008 Jul 29 |
|
A new haemodialysis catheter-locking agent reduces infections in haemodialysis patients. | 2008 Sep |
|
Wound healing is not impaired in rats undergoing perioperative treatment with the antineoplastic agent taurolidine. | 2009 |
|
The antibacterial substance taurolidine exhibits anti-neoplastic action based on a mixed type of programmed cell death. | 2009 Feb |
|
Taurolidine lock is highly effective in preventing catheter-related bloodstream infections in patients on home parenteral nutrition: a heparin-controlled prospective trial. | 2010 Aug |
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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 19:28:51 UTC 2023
by
admin
on
Sat Dec 16 19:28:51 UTC 2023
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Record UNII |
BJH2ZD8YGB
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Record Status |
Validated (UNII)
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Record Version |
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BJH2ZD8YGB
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46700836
Created by
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1333382-80-1
Created by
admin on Sat Dec 16 19:28:51 UTC 2023 , Edited by admin on Sat Dec 16 19:28:51 UTC 2023
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NON-SPECIFIC STOICHIOMETRY |
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PARENT -> SALT/SOLVATE |
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