U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Taurolidine: preclinical evaluation of a novel, highly selective, agent for bone marrow purging.
2002 Feb
The effect of taurolidine on brain tumor cells.
2002 Mar-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
Prophylaxis against dialysis catheter-related bacteremia with a novel antimicrobial lock solution.
2003 Jun 15
Taurine: new implications for an old amino acid.
2003 Sep 26
Diagnosis and treatment of catheter-related infections in paediatric oncology: an update.
2006 Jul
Pharmacokinetics of taurolidine following repeated intravenous infusions measured by HPLC-ESI-MS/MS of the derivatives taurultame and taurinamide in glioblastoma patients.
2007
Influence of intraperitoneal application of taurolidine/heparin on expression of adhesion molecules and colon cancer in rats undergoing laparoscopy.
2007 Jan
Noninvasive monitoring of myocardial function after surgical and cytostatic therapy in a peritoneal metastasis rat model: assessment with tissue Doppler and non-Doppler 2D strain echocardiography.
2007 Jul 12
TRAIL and Taurolidine induce apoptosis and decrease proliferation in human fibrosarcoma.
2008 Dec 12
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
[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
Taurolidine lock is highly effective in preventing catheter-related bloodstream infections in patients on home parenteral nutrition: a heparin-controlled prospective trial.
2010 Aug
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
  • Download
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
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE