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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
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
[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
The effect of taurolidine on brain tumor cells.
2002 Mar-Apr
Granulocyte colony-stimulating factor but not peritoneal lavage increases survival rate after experimental abdominal contamination and infection.
2002 Nov
Stability and in vitro efficacy of antibiotic-heparin lock solutions potentially useful for treatment of central venous catheter-related sepsis.
2003 Apr
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
Effects of taurolidine and octreotide on tumor growth and lipid peroxidation after staging-laparoscopy in ductal pancreatic cancer.
2003 Oct
Dialysis catheter-related bacteremia: treatment and prophylaxis.
2004 Nov
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
Effect of peritoneal lavage with taurolidine on primary colonic anastomosis in a rat model of secondary peritonitis.
2006
Diagnosis and treatment of catheter-related infections in paediatric oncology: an update.
2006 Jul
Catheter lock solutions: it's time for a change.
2006 Jul-Sep
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
Pharmacokinetics of taurolidine following repeated intravenous infusions measured by HPLC-ESI-MS/MS of the derivatives taurultame and taurinamide in glioblastoma patients.
2007
Taurolidine: a novel anti-neoplastic agent induces apoptosis of osteosarcoma cell lines.
2007 Aug
Influence of intraperitoneal application of taurolidine/heparin on expression of adhesion molecules and colon cancer in rats undergoing laparoscopy.
2007 Jan
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
Taurolidine induces apoptosis of murine melanoma cells in vitro and in vivo by modulation of the Bcl-2 family proteins.
2007 Sep 1
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
Using detachment-promoting agents for the prevention of chronic peritoneal dialysis-associated infections.
2008 Dec
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
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
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
Microbial inactivation properties of a new antimicrobial/antithrombotic catheter lock solution (citrate/methylene blue/parabens).
2009 Jun
Principles of the therapy of bone infections in adult extremities : Are there any new developments?
2009 Oct
Multimodal approach for treatment of peritoneal surface malignancies in a tumour-bearing rat model.
2010 Feb
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.
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