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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
Structure of Taurolidine citrate

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)

HIDE SMILES / InChI

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).

Approval Year

Targets
PubMed

PubMed

TitleDatePubMed
Two years' experience with Dialock and CLS (a new antimicrobial lock solution).
2001
Taurolidine improves survival by abrogating the accelerated development and proliferation of solid tumors and development of organ metastases from circulating tumor cells released following surgery.
2001 Dec
[Experimental study of antiseptic (tauroline, taurolidine) and antibiotic (sulmycin implant) drugs in vascular prosthesis infections in a standardized infection model].
2001 May
Taurolidine: cytotoxic and mechanistic evaluation of a novel antineoplastic agent.
2001 Sep 15
Effects of taurolidine and octreotide on port site and liver metastasis after laparoscopy in an animal model of pancreatic cancer.
2002
Prevention of hemodialysis catheter-related bloodstream infection using an antimicrobial lock.
2002
Taurolidine attenuates the hemodynamic and respiratory changes associated with endotoxemia.
2002 Apr
Taurolidine: preclinical evaluation of a novel, highly selective, agent for bone marrow purging.
2002 Feb
The antibacterial drug taurolidine induces apoptosis by a mitochondrial cytochrome c-dependent mechanism.
2002 Jul-Aug
A randomized double-blinded placebo-controlled crossover trial of nebulized taurolidine in adult cystic fibrosis patients infected with Burkholderia cepacia.
2002 Spring
Local and systemic chemotherapy with taurolidine and taurolidine/heparin in colon cancer-bearing rats undergoing laparotomy.
2003
The influence of adhesion prophylactic substances and taurolidine/heparin on local recurrence and intraperitoneal tumor growth after laparoscopic-assisted bowel resection of colon carcinoma in a rat model.
2003 Jul
Prophylaxis against dialysis catheter-related bacteremia with a novel antimicrobial lock solution.
2003 Jun 15
Enhancement of Fas-ligand-mediated programmed cell death by taurolidine.
2003 May-Jun
Effects of taurolidine and octreotide on tumor growth and lipid peroxidation after staging-laparoscopy in ductal pancreatic cancer.
2003 Oct
Taurine: new implications for an old amino acid.
2003 Sep 26
Prevention of dialysis catheter-related sepsis with a citrate-taurolidine-containing lock solution.
2004 Jun
Taurolidine-Fibrin-Sealant-Matrix using spray application for local treatment of brain tumors.
2004 Mar-Apr
Treatment of glioblastoma with intravenous taurolidine. First clinical experience.
2004 Mar-Apr
Mechanistic and antineoplastic evaluation of taurolidine in the DU145 model of human prostate cancer.
2004 Sep
Effects of increasing doses of a bolus injection and an intravenous long-term therapy of taurolidine on subcutaneous (metastatic) tumor growth in rats.
2005
Comment on 'in vivo effects of fluoroquinolones on rabbit corneas'.
2005 Feb
Induction of reactive oxygen intermediates-dependent programmed cell death in human malignant ex vivo glioma cells and inhibition of the vascular endothelial growth factor production by taurolidine.
2005 Jun
Peritoneal taurolidine lavage in children with localised peritonitis due to appendicitis.
2005 Jun
[Diagnostics and management of central venous line infections in pediatric cancer patients].
2005 Nov
High doses of taurolidine inhibit advanced intraperitoneal tumor growth in rats.
2005 Nov
Taurolidine--a new drug with anti-tumor and anti-angiogenic effects.
2005 Oct
Anti-inflammatory effects of taurine derivatives (taurine chloramine, taurine bromamine, and taurolidine) are mediated by different mechanisms.
2006
Hyaluronic acid/carboxymethylcellulose membrane barrier versus taurolidine for the prevention of adhesions to polypropylene mesh.
2006
Effect of peritoneal lavage with taurolidine on primary colonic anastomosis in a rat model of secondary peritonitis.
2006
Co-immunotherapy with interleukin-2 and taurolidine for progressive metastatic melanoma.
2006 Jan-Mar
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
Estimating in vivo airway surface liquid concentration in trials of inhaled antibiotics.
2007 Fall
Influence of intraperitoneal application of taurolidine/heparin on expression of adhesion molecules and colon cancer in rats undergoing laparoscopy.
2007 Jan
Synergistic effects in apoptosis induction by taurolidine and TRAIL in HCT-15 colon carcinoma cells.
2007 Nov-Dec
Leukopoiesis is not affected after intravenous treatment with the novel antineoplastic agent taurolidine. Results of an experimental study in rats.
2008
Taurolidine and catheter-related bloodstream infection: a systematic review of the literature.
2008 Aug
Re: Endophthalmitis: a review of current evaluation and management.
2008 Feb
An evaluation of normal saline and taurolidine on intra-abdominal adhesion formation and peritoneal fibrinolysis.
2008 Jan
The effect of taurolidine on experimental thrombus formation.
2008 Jan 14
Taurolidine-citrate lock solution (TauroLock) significantly reduces CVAD-associated grampositive infections in pediatric cancer patients.
2008 Jul 29
Synergistic apoptotic effects of taurolidine and TRAIL on squamous carcinoma cells of the esophagus.
2008 Jun
Novel anti-angiogenic compounds for application in tumor therapy - COP9 signalosome-associated kinases as possible targets.
2008 May
Effects of topical application of taurolidine on second intention healing of experimentally induced wounds in rats.
2008 Sep
Taurolidine lock is highly effective in preventing catheter-related bloodstream infections in patients on home parenteral nutrition: a heparin-controlled prospective trial.
2010 Aug
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
Patents

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
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 Sat Dec 16 19:28:51 GMT 2023
Edited
by admin
on Sat Dec 16 19:28:51 GMT 2023
Record UNII
BJH2ZD8YGB
Record Status Validated (UNII)
Record Version
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Name Type Language
Taurolidine citrate
Common Name English
Taurolidine citrate [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
BJH2ZD8YGB
Created by admin on Sat Dec 16 19:28:51 GMT 2023 , Edited by admin on Sat Dec 16 19:28:51 GMT 2023
PRIMARY
PUBCHEM
46700836
Created by admin on Sat Dec 16 19:28:51 GMT 2023 , Edited by admin on Sat Dec 16 19:28:51 GMT 2023
PRIMARY
CAS
1333382-80-1
Created by admin on Sat Dec 16 19:28:51 GMT 2023 , Edited by admin on Sat Dec 16 19:28:51 GMT 2023
NON-SPECIFIC STOICHIOMETRY
Related Record Type Details
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PARENT -> SALT/SOLVATE