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
Two years' experience with Dialock and CLS (a new antimicrobial lock solution).
2001
[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
Taurolidine attenuates the hemodynamic and respiratory changes associated with endotoxemia.
2002 Apr
A randomized double-blinded placebo-controlled crossover trial of nebulized taurolidine in adult cystic fibrosis patients infected with Burkholderia cepacia.
2002 Spring
Intravitreal taurolidine against experimental Staphylococcus epidermidis endophthalmitis in rabbits.
2004 Apr
Treatment of glioblastoma with intravenous taurolidine. First clinical experience.
2004 Mar-Apr
The tumor-suppressive reagent taurolidine is an inhibitor of protein biosynthesis.
2004 Nov 1
Comment on 'in vivo effects of fluoroquinolones on rabbit corneas'.
2005 Feb
Anti-inflammatory effects of taurine derivatives (taurine chloramine, taurine bromamine, and taurolidine) are mediated by different mechanisms.
2006
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
Instillation of taurolidine/heparin after laparotomy reduces intraperitoneal tumour growth in a colon cancer rat model.
2007
Taurolidine and povidone-iodine induce different types of cell death in malignant pleural mesothelioma.
2007 Jun
Local recurrence model of malignant pleural mesothelioma for investigation of intrapleural treatment.
2007 May
TRAIL and Taurolidine induce apoptosis and decrease proliferation in human fibrosarcoma.
2008 Dec 12
Taurolidine-citrate lock solution (TauroLock) significantly reduces CVAD-associated grampositive infections in pediatric cancer patients.
2008 Jul 29
A new haemodialysis catheter-locking agent reduces infections in haemodialysis patients.
2008 Sep
Wound healing is not impaired in rats undergoing perioperative treatment with the antineoplastic agent taurolidine.
2009
The antibacterial substance taurolidine exhibits anti-neoplastic action based on a mixed type of programmed cell death.
2009 Feb
Taurolidine lock is highly effective in preventing catheter-related bloodstream infections in patients on home parenteral nutrition: a heparin-controlled prospective trial.
2010 Aug
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 19:28:51 UTC 2023
Edited
by admin
on Sat Dec 16 19:28:51 UTC 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 UTC 2023 , Edited by admin on Sat Dec 16 19:28:51 UTC 2023
PRIMARY
PUBCHEM
46700836
Created by admin on Sat Dec 16 19:28:51 UTC 2023 , Edited by admin on Sat Dec 16 19:28:51 UTC 2023
PRIMARY
CAS
1333382-80-1
Created by admin on Sat Dec 16 19:28:51 UTC 2023 , Edited by admin on Sat Dec 16 19:28:51 UTC 2023
NON-SPECIFIC STOICHIOMETRY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE