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T7329

Sigma-Aldrich

Taurolidine

>97% (NMR), powder

Synonym(s):

4,4′-Methylenebis(tetrahydro-1,2,4-sulfadiazine 1,1-dioxide), Taurolin, Tauroline

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About This Item

Empirical Formula (Hill Notation):
C7H16N4O4S2
CAS Number:
19388-87-5
Molecular Weight:
284.36
EC Number:
243-016-5
MDL number:
MFCD00865076
UNSPSC Code:
12352200
PubChem Substance ID:
329826864
NACRES:
NA.77

Assay

>97% (NMR)

form

powder

storage condition

protect from light

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

room temp

SMILES string

O=S1(=O)CCN(CN1)CN2CCS(=O)(=O)NC2

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

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Biochem/physiol Actions

Taurolidine is a broad spectrum antibiotic with antineoplastic activity, which induces apoptosis and decreases tumor cell proliferation. Taurolidine has been used with TNF-related-apoptosis-inducing ligand (TRAIL) to characterize synergistic responses in many apoptosis related signaling-proteins. Tauroline is also being used as a tool to study the various mechanisms of apoptosis and necrosis.
Taurolidine is an antibacterial agent that can be used for the treatment of peritonis. It has also been used as an antiendoxic substance for systematic inflammatory response syndrome and as an anti-angiogenic agent for tumors. Furthermore, studies have reported that taurolidine can be used for the prevention of multiple catheter-related bloodstream infections.

Preparation Note

Taurolidine is soluble in DMSO at a concentration that is greater than 20 mg/ml.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Vassilis Filiopoulos et al.
American journal of nephrology, 33(3), 260-268 (2011-03-05)
Use of uncuffed catheters (UCs) in hemodialysis patients is common practice. An antibiotic lock has been recommended to prevent catheter-related bacteremia (CRB), although insufficient data are available about the appropriate antimicrobial agent and dose with prolonged use of UCs. This
Peter M Neary et al.
Annals of surgical oncology, 17(4), 1135-1143 (2009-12-30)
Taurolidine consists of two taurinamide rings derived from the naturally occurring amino acid taurine. It has been utilized to prevent adhesions, as an antimicrobial, and as an anti-inflammatory agent. More recently, it has been found to exert antineoplastic activity. We
Joanne H Bradshaw et al.
Journal of pediatric gastroenterology and nutrition, 47(2), 179-186 (2008-07-31)
Catheter-related bloodstream infection remains the most common serious complication associated with long-term parenteral nutrition. Taurolock (Bio-Implant HealthCare, Winsen, Germany), which contains taurolidine, is being marketed as a central venous catheter lock solution for decreasing the risk of catheter sepsis. To
Adrien Daigeler et al.
Ultrasound in medicine & biology, 36(11), 1893-1906 (2010-09-28)
Sonodynamic therapy, in combination with ultrasound contrast agents, proved to enhance the uptake of chemotherapeutics in malignant cells. HT1080 fibrosarcoma cells were treated in vitro with a combination of ultrasound SonoVue™-microbubbles and taurolidine (TRD) plus tumor necrosis factor related apoptosis
M J Dümichen et al.
The Journal of hospital infection, 80(4), 304-309 (2012-02-22)
A catheter lock solution containing 1.35% taurolidine and 4% citrate could potentially disrupt bacterial surface adherence and consecutive biofilm production due to the anti-adherence properties of taurolidine and the anticlotting and chelator activities of both compounds. To compare the impact
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