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
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
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).
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 |
---|---|---|
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 |
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 17:19:41 GMT 2023
by
admin
on
Sat Dec 16 17:19:41 GMT 2023
|
Record UNII |
8OBZ1M4V3V
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
|
||
|
METABOLITE -> PARENT | |||
|
METABOLITE -> PARENT | |||
|
METABOLITE ACTIVE -> PARENT |
|
||
|
METABOLITE ACTIVE -> PARENT |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|