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19388-87-5 | Taurolidin
CAS No: 19388-87-5 Catalog No: AG003UHO MDL No:MFCD00865076
Product Description
Catalog Number:
AG003UHO
Chemical Name:
Taurolidin
CAS Number:
19388-87-5
Molecular Formula:
C7H16N4O4S2
Molecular Weight:
284.3563
MDL Number:
MFCD00865076
IUPAC Name:
4-[(1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide
InChI:
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
InChI Key:
AJKIRUJIDFJUKJ-UHFFFAOYSA-N
SMILES:
O=S1(=O)CCN(CN1)CN1CCS(=O)(=O)NC1
EC Number:
243-016-5
UNII:
8OBZ1M4V3V
Properties
Complexity:
419
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
284.061g/mol
Formal Charge:
0
Heavy Atom Count:
17
Hydrogen Bond Acceptor Count:
8
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
284.349g/mol
Monoisotopic Mass:
284.061g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
116A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.7
Literature
| Title | Journal |
|---|---|
| Taurolidine: mode of administration in mouse tumor models. | International journal of cancer 20121201 |
| Significant reduction in central venous catheter-related bloodstream infections in children on HPN after starting treatment with taurolidine line lock. | Journal of pediatric gastroenterology and nutrition 20121001 |
| Biofilm formation in long-term central venous catheters in children with cancer: a randomized controlled open-labelled trial of taurolidine versus heparin. | APMIS : acta pathologica, microbiologica, et immunologica Scandinavica 20121001 |
| Taurolidine: Mode of administration in mouse tumor models. | International journal of cancer 20120915 |
| The antineoplastic antibiotic taurolidine promotes lung and liver metastasis in two syngeneic osteosarcoma mouse models and exhibits severe liver toxicity. | International journal of cancer 20120901 |
| Taurolidine lock solution in the secondary prevention of central venous catheter-associated bloodstream infection in home parenteral nutrition patients. | Clinical nutrition (Edinburgh, Scotland) 20120801 |
| TRAIL and taurolidine enhance the anticancer activity of doxorubicin, trabectedin and mafosfamide in HT1080 human fibrosarcoma cells. | Anticancer research 20120701 |
| Efficacy of taurolidine against periodontopathic species--an in vitro study. | Clinical oral investigations 20120601 |
| Taxol and taurine protect the renal tissue of rats after unilateral ureteral obstruction: a stereological survey. | Korean journal of urology 20120501 |
| Antibacterial effect of taurolidine (2%) on established dental plaque biofilm. | Clinical oral investigations 20120401 |
| Randomized controlled trial of taurolidine citrate versus heparin as catheter lock solution in paediatric patients with haematological malignancies. | The Journal of hospital infection 20120401 |
| Observational study of need for thrombolytic therapy and incidence of bacteremia using taurolidine-citrate-heparin, taurolidine-citrate and heparin catheter locks in patients treated with hemodialysis. | Seminars in dialysis 20120101 |
| Taurolidine use as a Scolicidal Agent: We Need Different Methodologies. | Turkiye parazitolojii dergisi 20120101 |
| In vitro screening of synergistic ascorbate-drug combinations for the treatment of malignant mesothelioma. | Toxicology in vitro : an international journal published in association with BIBRA 20111201 |
| Chemical pleurodesis for the management of refractory hepatic hydrothorax in patients with decompensated liver cirrhosis. | The Korean journal of hepatology 20111201 |
| Toxicity of antiseptics against chondrocytes: what is best for the cartilage in septic joint surgery? | International orthopaedics 20111101 |
| [Tunnelled internal jugular vein catheters with taurolidine lock: an acceptable challenge to arterio-venous fistula in 70 years old haemodialyzed patients: a prospective pilot study]. | Nephrologie & therapeutique 20110701 |
| Taurolidine lock - experience from the West of Scotland. | Clinical nutrition (Edinburgh, Scotland) 20110601 |
| Endotoxin release in cardiac surgery with cardiopulmonary bypass: pathophysiology and possible therapeutic strategies. An update. | European journal of cardio-thoracic surgery : official journal of the European Association for Cardio-thoracic Surgery 20110401 |
| Advances in the diagnosis and management of central venous access device infections in children. | Advances in experimental medicine and biology 20110101 |
| Unsuccessful application of taurolidine in the treatment of fungal peritonitis in peritoneal dialysis. | Clinical nephrology 20110101 |
| Animal models of bacterial keratitis. | Journal of biomedicine & biotechnology 20110101 |
| Animal models of colitis-associated carcinogenesis. | Journal of biomedicine & biotechnology 20110101 |
| Treatment of long-term catheter-related bloodstream infections with a taurolidine block: a single cancer center experience. | The journal of vascular access 20110101 |
| Approaches to prolong the use of uncuffed hemodialysis catheters: results of a randomized trial. | American journal of nephrology 20110101 |
| Role of mutagenicity in asbestos fiber-induced carcinogenicity and other diseases. | Journal of toxicology and environmental health. Part B, Critical reviews 20110101 |
| Cytoreductive surgery plus hyperthermic intraperitoneal chemotherapy improves survival of gastric cancer with peritoneal carcinomatosis: evidence from an experimental study. | Journal of translational medicine 20110101 |
| Synergistic effects of sonoporation and taurolidin/TRAIL on apoptosis in human fibrosarcoma. | Ultrasound in medicine & biology 20101101 |
| The antiendotoxin agent taurolidine potentially reduces ischemia/reperfusion injury through its metabolite taurine. | Surgery 20100901 |
| Taurolidine lock is highly effective in preventing catheter-related bloodstream infections in patients on home parenteral nutrition: a heparin-controlled prospective trial. | Clinical nutrition (Edinburgh, Scotland) 20100801 |
| A randomized double-blind controlled trial of taurolidine-citrate catheter locks for the prevention of bacteremia in patients treated with hemodialysis. | American journal of kidney diseases : the official journal of the National Kidney Foundation 20100601 |
| The evolving role of taurolidine in cancer therapy. | Annals of surgical oncology 20100401 |
| Multimodal approach for treatment of peritoneal surface malignancies in a tumour-bearing rat model. | International journal of colorectal disease 20100201 |
| Taurolidine antiadhesive properties on interaction with E. coli; its transformation in biological environment and interaction with bacteria cell wall. | PloS one 20100101 |
| Comparative analysis of cell death induction by Taurolidine in different malignant human cancer cell lines. | Journal of experimental & clinical cancer research : CR 20100101 |
| Establishment and identification of a rabbit model of peritoneal carcinomatosis from gastric cancer. | BMC cancer 20100101 |
| Oral administration of the anti-proliferative substance taurolidine has no impact on dextran sulfate sodium induced colitis-associated carcinogenesis in mice. | Journal of carcinogenesis 20100101 |
| Taurine and the renal system. | Journal of biomedical science 20100101 |
| [The protoskolicidal effect of 1% polyvinylpyrrolidone-iodine (PVP-1) and 2% taurolidine on abdominal hydatidosis]. | Turkiye parazitolojii dergisi 20100101 |
| Gene expression analysis of cell death induction by taurolidine in different malignant cell lines. | BMC cancer 20100101 |
| Taurolidine and oxidative stress: a rationale for local treatment of mesothelioma. | The European respiratory journal 20091201 |
| Taurolidine in the prevention and therapy of lung metastases. | European journal of cardio-thoracic surgery : official journal of the European Association for Cardio-thoracic Surgery 20091201 |
| Principles of the therapy of bone infections in adult extremities : Are there any new developments? | Strategies in trauma and limb reconstruction (Online) 20091001 |
| Divergent effects of taurolidine as potential anti-neoplastic agent: inhibition of bladder carcinoma cells in vitro and promotion of bladder tumor in vivo. | Oncology reports 20090801 |
| [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]. | Zentralblatt fur Chirurgie 20090801 |
| Microbial inactivation properties of a new antimicrobial/antithrombotic catheter lock solution (citrate/methylene blue/parabens). | Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20090601 |
| The antibacterial substance taurolidine exhibits anti-neoplastic action based on a mixed type of programmed cell death. | Autophagy 20090201 |
| Wound healing is not impaired in rats undergoing perioperative treatment with the antineoplastic agent taurolidine. | European surgical research. Europaische chirurgische Forschung. Recherches chirurgicales europeennes 20090101 |
| Taurolidine reduces the tumor stimulating cytokine interleukin-1beta in patients with resectable gastrointestinal cancer: a multicentre prospective randomized trial. | World journal of surgical oncology 20090101 |
| All-you-can-eat: autophagy in neurodegeneration and neuroprotection. | Molecular neurodegeneration 20090101 |
| Arsenic trioxide exerts synergistic effects with cisplatin on non-small cell lung cancer cells via apoptosis induction. | Journal of experimental & clinical cancer research : CR 20090101 |
| Using detachment-promoting agents for the prevention of chronic peritoneal dialysis-associated infections. | Artificial organs 20081201 |
| Effects of topical application of taurolidine on second intention healing of experimentally induced wounds in rats. | American journal of veterinary research 20080901 |
| A new haemodialysis catheter-locking agent reduces infections in haemodialysis patients. | Journal of renal care 20080901 |
| Taurolidine and catheter-related bloodstream infection: a systematic review of the literature. | Journal of pediatric gastroenterology and nutrition 20080801 |
| Synergistic apoptotic effects of taurolidine and TRAIL on squamous carcinoma cells of the esophagus. | International journal of oncology 20080601 |
| Novel anti-angiogenic compounds for application in tumor therapy - COP9 signalosome-associated kinases as possible targets. | Mini reviews in medicinal chemistry 20080501 |
| Re: Endophthalmitis: a review of current evaluation and management. | Retina (Philadelphia, Pa.) 20080201 |
| The effect of taurolidine on experimental thrombus formation. | European journal of pharmacology 20080114 |
| An evaluation of normal saline and taurolidine on intra-abdominal adhesion formation and peritoneal fibrinolysis. | The Journal of surgical research 20080101 |
| Leukopoiesis is not affected after intravenous treatment with the novel antineoplastic agent taurolidine. Results of an experimental study in rats. | European surgical research. Europaische chirurgische Forschung. Recherches chirurgicales europeennes 20080101 |
| Taurolidine-citrate lock solution (TauroLock) significantly reduces CVAD-associated grampositive infections in pediatric cancer patients. | BMC infectious diseases 20080101 |
| TRAIL and Taurolidine induce apoptosis and decrease proliferation in human fibrosarcoma. | Journal of experimental & clinical cancer research : CR 20080101 |
| The tumor suppressive reagent taurolidine inhibits growth of malignant melanoma--a mouse model. | The Journal of surgical research 20071201 |
| Intra-abdominal use of taurolidine or heparin as alternative products to an antiadhesive barrier (Seprafilm) in adhesion prevention: an experimental study on mice. | Diseases of the colon and rectum 20071201 |
| Taurolidine induces apoptosis of murine melanoma cells in vitro and in vivo by modulation of the Bcl-2 family proteins. | Journal of surgical oncology 20070901 |
| Taurolidine: a novel anti-neoplastic agent induces apoptosis of osteosarcoma cell lines. | Investigational new drugs 20070801 |
| Peritoneal instillation of taurolidine or polihexanide modulates intestinal microcirculation in experimental endotoxemia. | International journal of colorectal disease 20070701 |
| Taurolidine and povidone-iodine induce different types of cell death in malignant pleural mesothelioma. | Lung cancer (Amsterdam, Netherlands) 20070601 |
| The pharmacokinetics of taurolidine metabolites in healthy volunteers. | Journal of clinical pharmacology 20070601 |
| Local recurrence model of malignant pleural mesothelioma for investigation of intrapleural treatment. | European journal of cardio-thoracic surgery : official journal of the European Association for Cardio-thoracic Surgery 20070501 |
| Influence of intraperitoneal application of taurolidine/heparin on expression of adhesion molecules and colon cancer in rats undergoing laparoscopy. | The Journal of surgical research 20070101 |
| Instillation of taurolidine/heparin after laparotomy reduces intraperitoneal tumour growth in a colon cancer rat model. | European surgical research. Europaische chirurgische Forschung. Recherches chirurgicales europeennes 20070101 |
| Pharmacokinetics of taurolidine following repeated intravenous infusions measured by HPLC-ESI-MS/MS of the derivatives taurultame and taurinamide in glioblastoma patients. | Clinical pharmacokinetics 20070101 |
| Is Taurolidine a candidate for treatment of rheumatoid arthritis? | Clinical and experimental rheumatology 20070101 |
| Treatment of multiple liver metastasis from gastric carcinoma. | World journal of surgical oncology 20070101 |
| 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. | Cardiovascular ultrasound 20070101 |
| Estimating in vivo airway surface liquid concentration in trials of inhaled antibiotics. | Journal of aerosol medicine : the official journal of the International Society for Aerosols in Medicine 20070101 |
| Oral administration of taurolidine ameliorates chronic DSS colitis in mice. | Journal of investigative surgery : the official journal of the Academy of Surgical Research 20070101 |
| Synergistic effects in apoptosis induction by taurolidine and TRAIL in HCT-15 colon carcinoma cells. | Journal of investigative surgery : the official journal of the Academy of Surgical Research 20070101 |
| Diagnosis and treatment of catheter-related infections in paediatric oncology: an update. | Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20060701 |
| Co-immunotherapy with interleukin-2 and taurolidine for progressive metastatic melanoma. | Irish journal of medical science 20060101 |
| Effect of peritoneal lavage with taurolidine on primary colonic anastomosis in a rat model of secondary peritonitis. | Surgery today 20060101 |
| 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. | World journal of surgical oncology 20060101 |
| Hyaluronic acid/carboxymethylcellulose membrane barrier versus taurolidine for the prevention of adhesions to polypropylene mesh. | European surgical research. Europaische chirurgische Forschung. Recherches chirurgicales europeennes 20060101 |
| Catheter lock solutions: it's time for a change. | The journal of vascular access 20060101 |
| Anti-inflammatory effects of taurine derivatives (taurine chloramine, taurine bromamine, and taurolidine) are mediated by different mechanisms. | Advances in experimental medicine and biology 20060101 |
| High doses of taurolidine inhibit advanced intraperitoneal tumor growth in rats. | The Journal of surgical research 20051101 |
| [Diagnostics and management of central venous line infections in pediatric cancer patients]. | Klinische Padiatrie 20051101 |
| Taurolidine--a new drug with anti-tumor and anti-angiogenic effects. | Anti-cancer drugs 20051001 |
| Taurolidine lock: the key to prevention of recurrent catheter-related bloodstream infections. | Clinical nutrition (Edinburgh, Scotland) 20050601 |
| Peritoneal taurolidine lavage in children with localised peritonitis due to appendicitis. | Pediatric surgery international 20050601 |
| Induction of reactive oxygen intermediates-dependent programmed cell death in human malignant ex vivo glioma cells and inhibition of the vascular endothelial growth factor production by taurolidine. | Journal of neurosurgery 20050601 |
| Impact of taurolidin and octreotide on liver metastasis and lipid peroxidation after laparoscopy in chemical induced ductal pancreatic cancer. | Investigational new drugs 20050301 |
| Effectiveness of topical taurolidine versus ciprofloxacin, ofloxacin, and fortified cefazolin in a rabbit Staphylococcus aureus keratitis model. | Current eye research 20050301 |
| Comment on 'in vivo effects of fluoroquinolones on rabbit corneas'. | Clinical & experimental ophthalmology 20050201 |
| Impact of taurolidine on the growth of CC531 coloncarcinoma cells in vitro and in a laparoscopic animal model in rats. | Surgical endoscopy 20050201 |
| Effects of increasing doses of a bolus injection and an intravenous long-term therapy of taurolidine on subcutaneous (metastatic) tumor growth in rats. | Clinical & experimental metastasis 20050101 |
| The effects of taurolidine, a novel antineoplastic agent, on human malignant mesothelioma. | Clinical cancer research : an official journal of the American Association for Cancer Research 20041115 |
| The tumor-suppressive reagent taurolidine is an inhibitor of protein biosynthesis. | International journal of cancer 20041101 |
| Dialysis catheter-related bacteremia: treatment and prophylaxis. | American journal of kidney diseases : the official journal of the National Kidney Foundation 20041101 |
| Taurolidine is effective in the treatment of central venous catheter-related bloodstream infections in cancer patients. | International journal of antimicrobial agents 20041101 |
| Mechanistic and antineoplastic evaluation of taurolidine in the DU145 model of human prostate cancer. | Cancer chemotherapy and pharmacology 20040901 |
| Prevention of dialysis catheter-related sepsis with a citrate-taurolidine-containing lock solution. | Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20040601 |
| Irrigation of port sites: prevention of port site metastases? | Journal of laparoendoscopic & advanced surgical techniques. Part A 20040601 |
| Intravitreal taurolidine against experimental Staphylococcus epidermidis endophthalmitis in rabbits. | Current eye research 20040401 |
| Treatment of glioblastoma with intravenous taurolidine. First clinical experience. | Anticancer research 20040101 |
| Taurolidine-Fibrin-Sealant-Matrix using spray application for local treatment of brain tumors. | Anticancer research 20040101 |
| Challenges in ocular infectious diseases and the evolution of anti-infective therapy. | Survey of ophthalmology 20040101 |
| Effects of taurolidine and octreotide on tumor growth and lipid peroxidation after staging-laparoscopy in ductal pancreatic cancer. | Prostaglandins, leukotrienes, and essential fatty acids 20031001 |
| Taurine: new implications for an old amino acid. | FEMS microbiology letters 20030926 |
| 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. | Surgical endoscopy 20030701 |
| Prophylaxis against dialysis catheter-related bacteremia with a novel antimicrobial lock solution. | Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20030615 |
| Stability and in vitro efficacy of antibiotic-heparin lock solutions potentially useful for treatment of central venous catheter-related sepsis. | The Journal of antimicrobial chemotherapy 20030401 |
| The effect of Taurolidine on adherent and floating subpopulations of melanoma cells. | Anti-cancer drugs 20030401 |
| [In vitro effect of taurolidine on squamous cell carcinoma in the oral cavity]. | Mund-, Kiefer- und Gesichtschirurgie : MKG 20030301 |
| Enhancement of Fas-ligand-mediated programmed cell death by taurolidine. | Anticancer research 20030101 |
| Local and systemic chemotherapy with taurolidine and taurolidine/heparin in colon cancer-bearing rats undergoing laparotomy. | Clinical & experimental metastasis 20030101 |
| Novel therapies for sepsis: antiendotoxin therapies. | Expert opinion on investigational drugs 20021201 |
| Granulocyte colony-stimulating factor but not peritoneal lavage increases survival rate after experimental abdominal contamination and infection. | The British journal of surgery 20021101 |
| Activity of disinfectants against Gram-negative bacilli isolated from patients undergoing lung transplantation for cystic fibrosis. | The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation 20021101 |
| Taurolidine attenuates the hemodynamic and respiratory changes associated with endotoxemia. | Shock (Augusta, Ga.) 20020401 |
| Taurolidine: preclinical evaluation of a novel, highly selective, agent for bone marrow purging. | Bone marrow transplantation 20020201 |
| Prevention of hemodialysis catheter-related bloodstream infection using an antimicrobial lock. | Blood purification 20020101 |
| Effects of taurolidine and octreotide on port site and liver metastasis after laparoscopy in an animal model of pancreatic cancer. | Clinical & experimental metastasis 20020101 |
| A randomized double-blinded placebo-controlled crossover trial of nebulized taurolidine in adult cystic fibrosis patients infected with Burkholderia cepacia. | Journal of aerosol medicine : the official journal of the International Society for Aerosols in Medicine 20020101 |
| The effect of taurolidine on brain tumor cells. | Anticancer research 20020101 |
| The antibacterial drug taurolidine induces apoptosis by a mitochondrial cytochrome c-dependent mechanism. | Anticancer research 20020101 |
| Influence of antiseptic agents on interleukin-8 release and transmigration of polymorphonuclear neutrophils in a human in vitro model of peritonitis. | Surgical infections 20020101 |
| 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. | The Journal of surgical research 20011201 |
| Taurolidine: cytotoxic and mechanistic evaluation of a novel antineoplastic agent. | Cancer research 20010915 |
| [Experimental study of antiseptic (tauroline, taurolidine) and antibiotic (sulmycin implant) drugs in vascular prosthesis infections in a standardized infection model]. | Zentralblatt fur Chirurgie 20010501 |
| Two years' experience with Dialock and CLS (a new antimicrobial lock solution). | Blood purification 20010101 |
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