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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

Quality Level

100

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Mette Møller Handrup et al.
APMIS : acta pathologica, microbiologica, et immunologica Scandinavica, 120(10), 794-801 (2012-09-11)
Taurolidine has demonstrated inhibition of biofilm formation in vitro. The aim of this study was to compare the effect of catheter locking with taurolidine vs heparin in biofilm formation in central venous catheters. Forty-eight children with cancer were randomized to
Kevin Marley et al.
BMC veterinary research, 9, 15-15 (2013-01-22)
Osteosarcoma (OS) affects over 8000 dogs/year in the United States. The disease usually arises in the appendicular skeleton and metastasizes to the lung. Dogs with localized appendicular disease benefit from limb amputation and chemotherapy but most die within 6-12 months
Justyna Schubert et al.
Scientific reports, 10(1), 10341-10341 (2020-06-27)
For decades, intraperitoneal chemotherapy (IPC) was delivered into the abdominal cavity as a liquid solution. This preliminary study aims to evaluate foam as a potential new drug carrier for IPC delivery. Foam-based intraperitoneal chemotherapy (FBIC) was produced with taurolidine, hydrogen
Christoph A Jacobi et al.
Anti-cancer drugs, 16(9), 917-921 (2005-09-16)
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. It was mainly used in the treatment of patients with peritonis as well as antiendoxic agent in patients with systematic inflammatory response syndrome.
ESPGHAN/ESPEN/ESPR/CSPEN guidelines on pediatric parenteral nutrition: Venous access.
S Kolaček et al.
Clinical nutrition (Edinburgh, Scotland), 37(6 Pt B), 2379-2391 (2018-07-30)
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