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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
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
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
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
Taurine: new implications for an old amino acid.
2003 Sep 26
Intravitreal taurolidine against experimental Staphylococcus epidermidis endophthalmitis in rabbits.
2004 Apr
Impact of taurolidine on the growth of CC531 coloncarcinoma cells in vitro and in a laparoscopic animal model in rats.
2005 Feb
Peritoneal taurolidine lavage in children with localised peritonitis due to appendicitis.
2005 Jun
Taurolidine lock: the key to prevention of recurrent catheter-related bloodstream infections.
2005 Jun
[Diagnostics and management of central venous line infections in pediatric cancer patients].
2005 Nov
Hyaluronic acid/carboxymethylcellulose membrane barrier versus taurolidine for the prevention of adhesions to polypropylene mesh.
2006
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
Taurolidine and povidone-iodine induce different types of cell death in malignant pleural mesothelioma.
2007 Jun
Is Taurolidine a candidate for treatment of rheumatoid arthritis?
2007 Mar-Apr
Local recurrence model of malignant pleural mesothelioma for investigation of intrapleural treatment.
2007 May
Taurolidine induces apoptosis of murine melanoma cells in vitro and in vivo by modulation of the Bcl-2 family proteins.
2007 Sep 1
Taurolidine and catheter-related bloodstream infection: a systematic review of the literature.
2008 Aug
TRAIL and Taurolidine induce apoptosis and decrease proliferation in human fibrosarcoma.
2008 Dec 12
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
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
Taurolidine reduces the tumor stimulating cytokine interleukin-1beta in patients with resectable gastrointestinal cancer: a multicentre prospective randomized trial.
2009 Mar 23
Taurolidine antiadhesive properties on interaction with E. coli; its transformation in biological environment and interaction with bacteria cell wall.
2010 Jan 28
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 17:19:41 GMT 2023
Edited
by admin
on Sat Dec 16 17:19:41 GMT 2023
Record UNII
8OBZ1M4V3V
Record Status Validated (UNII)
Record Version
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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 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
FDA ORPHAN DRUG 528816
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
FDA ORPHAN DRUG 500015
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
WHO-ATC B05CA05
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
WHO-VATC QB05CA05
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C2639
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
SMS_ID
100000082427
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
CAS
19388-87-5
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID00173001
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
INN
2885
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
MESH
C012566
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
EVMPD
SUB10837MIG
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
DRUG CENTRAL
2568
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
PUBCHEM
29566
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
WIKIPEDIA
TAUROLIDINE
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
ECHA (EC/EINECS)
243-016-5
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
MERCK INDEX
m10483
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL2105420
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
DRUG BANK
DB12473
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
FDA UNII
8OBZ1M4V3V
Created by admin on Sat Dec 16 17:19:41 GMT 2023 , Edited by admin on Sat Dec 16 17:19:41 GMT 2023
PRIMARY
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