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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
Structure of TAUROLIDINE

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

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

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
Intravitreal taurolidine against experimental Staphylococcus epidermidis endophthalmitis in rabbits.
2004 Apr
Irrigation of port sites: prevention of port site metastases?
2004 Jun
Taurolidine is effective in the treatment of central venous catheter-related bloodstream infections in cancer patients.
2004 Nov
The effects of taurolidine, a novel antineoplastic agent, on human malignant mesothelioma.
2004 Nov 15
Mechanistic and antineoplastic evaluation of taurolidine in the DU145 model of human prostate cancer.
2004 Sep
Impact of taurolidine on the growth of CC531 coloncarcinoma cells in vitro and in a laparoscopic animal model in rats.
2005 Feb
Taurolidine lock: the key to prevention of recurrent catheter-related bloodstream infections.
2005 Jun
Impact of taurolidin and octreotide on liver metastasis and lipid peroxidation after laparoscopy in chemical induced ductal pancreatic cancer.
2005 Mar
Taurolidine--a new drug with anti-tumor and anti-angiogenic effects.
2005 Oct
Hyaluronic acid/carboxymethylcellulose membrane barrier versus taurolidine for the prevention of adhesions to polypropylene mesh.
2006
Co-immunotherapy with interleukin-2 and taurolidine for progressive metastatic melanoma.
2006 Jan-Mar
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
Estimating in vivo airway surface liquid concentration in trials of inhaled antibiotics.
2007 Fall
Peritoneal instillation of taurolidine or polihexanide modulates intestinal microcirculation in experimental endotoxemia.
2007 Jul
Taurolidine and povidone-iodine induce different types of cell death in malignant pleural mesothelioma.
2007 Jun
Treatment of multiple liver metastasis from gastric carcinoma.
2007 Jun 21
Is Taurolidine a candidate for treatment of rheumatoid arthritis?
2007 Mar-Apr
Synergistic effects in apoptosis induction by taurolidine and TRAIL in HCT-15 colon carcinoma cells.
2007 Nov-Dec
Oral administration of taurolidine ameliorates chronic DSS colitis in mice.
2007 Sep-Oct
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
Using detachment-promoting agents for the prevention of chronic peritoneal dialysis-associated infections.
2008 Dec
TRAIL and Taurolidine induce apoptosis and decrease proliferation in human fibrosarcoma.
2008 Dec 12
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
A new haemodialysis catheter-locking agent reduces infections in haemodialysis patients.
2008 Sep
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
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
Arsenic trioxide exerts synergistic effects with cisplatin on non-small cell lung cancer cells via apoptosis induction.
2009 Aug 8
Taurolidine in the prevention and therapy of lung metastases.
2009 Dec
Taurolidine and oxidative stress: a rationale for local treatment of mesothelioma.
2009 Dec
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
Principles of the therapy of bone infections in adult extremities : Are there any new developments?
2009 Oct
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
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
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 17:19:41 UTC 2023
Edited
by admin
on Sat Dec 16 17:19:41 UTC 2023
Record UNII
8OBZ1M4V3V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAUROLIDINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
Taurolidine [WHO-DD]
Common Name English
4,4'-METHYLENEBIS(TETRAHYDRO-1,2,4-THIADIAZINE 1,1-DIOXIDE)
Common Name English
DEFENCATH COMPONENT TAUROLIDINE
Brand Name English
TAUROLIDINE [MI]
Common Name English
TAUROLIDINE [MART.]
Common Name English
TAUROLOCK COMPONENT TAUROLIDINE
Brand Name English
(CYCLO)-TAUROLIDINE
Common Name English
4,4'-METHYLENE-BIS(TETRAHYDRO-1,2,4-THIADIAZINE-1,1-DIOXIDE)
Common Name English
taurolidine [INN]
Common Name English
CYCLO-TAUROLIDINE
Common Name English
W-3100M
Code English
Classification Tree Code System Code
NCI_THESAURUS C258
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
FDA ORPHAN DRUG 528816
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
FDA ORPHAN DRUG 500015
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
WHO-ATC B05CA05
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
WHO-VATC QB05CA05
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C2639
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
SMS_ID
100000082427
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
CAS
19388-87-5
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID00173001
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
INN
2885
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
MESH
C012566
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
EVMPD
SUB10837MIG
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
DRUG CENTRAL
2568
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
PUBCHEM
29566
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
WIKIPEDIA
TAUROLIDINE
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
ECHA (EC/EINECS)
243-016-5
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
MERCK INDEX
m10483
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL2105420
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
DRUG BANK
DB12473
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
FDA UNII
8OBZ1M4V3V
Created by admin on Sat Dec 16 17:19:41 UTC 2023 , Edited by admin on Sat Dec 16 17:19:41 UTC 2023
PRIMARY
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