19388-87-5

Basic information

• Product Name: Taurolidine
• Synonyms: taurolin;4,4'-methylenebis[tetrahydro-2h-1,2,4-thiadiazine] 1,1,1',1'-tetraoxide;TAUROLIDINE;2H-1,2,4-Thiadiazine, 4,4'-methylenebis[tetrahydro-, 1,1,1',1'-tetraoxide;4,4'-Methylenebis(perhydro-1,2,4-thiadiazin 1,1-dioxide);4-[(1,1-Dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide;4,4'-Methylenebis(tetrahydro-2H-1,2,4-thiadiazine 1,1-dioxide);Tauroline
• CAS NO: 19388-87-5
• Molecular Formula: C₇H₁₆N₄O₄S₂
• Molecular Weight: 284.35634
• EINECS: 243-016-5
• Mol File: 19388-87-5.mol

Chemical Properties

• Melting Point: 154-158°
• Boiling Point: 471.214 °C at 760 mmHg
• Flash Point: 238.782 °C
• Appearance: white to off-white/
• Density: 1.467 g/cm³
• Vapor Pressure: 4.74E-09mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: room temp
• Solubility: DMSO: >20mg/mL
• PKA: 11.16±0.20(Predicted)
• Stability: Unstable in Aqueous Solution
• CAS DataBase Reference: Taurolidine(CAS DataBase Reference)
• NIST Chemistry Reference: Taurolidine(19388-87-5)
• EPA Substance Registry System: Taurolidine(19388-87-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 19388-87-5(Hazardous Substances Data)

Usage

Uses

Used in Healthcare Industry:
Taurolidine is used as an antiendotoxin agent for its ability to counteract the harmful effects of endotoxins, which are toxins released by gram-negative bacteria when they die or disintegrate. This property makes it a crucial component in the treatment of sepsis, a life-threatening condition caused by the body's response to infection.
Taurolidine is used as an antimicrobial agent for its ability to inhibit the growth of microorganisms, including bacteria and fungi. This characteristic is particularly useful in preventing and treating infections, especially in hospital settings where the risk of infection is high.
Taurolidine is used as an antitumor agent for its demonstrated in vitro and in vivo antitumor activity. It has the potential to be a valuable tool in the fight against cancer, as it can help to slow or stop the growth of cancer cells.
Used in Medical Device Industry:
Taurolidine is used as a preventive measure for catheter-related bloodstream infections. Its antimicrobial properties help to reduce the risk of infection associated with the use of medical devices such as catheters, which are commonly used in hospitals and other healthcare facilities.

Biological Activity

taurolidine is a synthetic taurine analog with antimicrobial and anti-neoplastic actions.taurine, a conditionally-essential amino acid, is not utilized in protein synthesis, but is found free or in simple peptides. taurine has been shown to be essential in mammalian development. in vitro studies have demonstrated that low levels of taurine are associated with various pathological lesions.

in vitro

previous study found that in selected human and murine tumor cell lines, a 3-day exposure to taurolidine could inhibit the growth of all of the cell lines. further mechanistic study showed that in nih-3t3 murine fibroblasts and the pa-1 and skov-3 human ovarian tumor cells, a 48-h exposure to taurolidine had little effect on cell cycle distribution in pa-1 and skov-3 cells but greatly increased the appearance of dna debris, an effect consistent with an induction of apoptosis. in contrast, in nih-3t3 cells, taurolidine exposure did not increase dna debris in the sub-g(0)/g(1) region [1].

in vivo

animal study found that the i.v. administration of 2% taurolidine and 3% taurolidine as well the i.p. application of 2% taurolidine could decrease the development of advanced i.p. tumor lesions. no changes of differential blood count nor relevant animal weight changes resulted. moreover, taurolidine did not impair the liver tissue, kidneys, svc, and leucopoiesis. the intravenous therapy of 2% taurolidine was found to be safe and anti-tumorigenic in advanced local tumor growth in rats [2].

IC 50

9.6-34.2 microm for several cancer cell lines

references

[1] calabresi, p. ,goulette, f.a. and darnowski, j.w. taurolidine: cytotoxic and mechanistic evaluation of a novel antineoplastic agent. cancer research 61(18), 6816-6821 (2001).[2] braumann c, stuhldreier b, bobrich e, menenakos c, rogalla s, jacobi ca. high doses of taurolidine inhibit advanced intraperitoneal tumor growth in rats. j surg res. 2005 nov;129(1):129-35.

InChI:InChI=1/C7H16N4O4S2/c12-16(13)3-1-10(5-8-16)7-11-2-4-17(14,15)9-6-11/h8-9H,1-7H2

Upstream product

• 50-00-0 formaldehyd 
• 1378969-27-7 taurinamide succinate 

Downstream Products

• 18996-35-5 sodium dihydrogencitrate 

Related news

Original articleClinical outcomes of home parenteral nutrition patients using Taurolidine (cas 19388-87-5) as catheter lock: A long-term cohort study08/13/2019

SummaryBackground & aimsCentral venous access device (CVAD)-related complications, such as central-line associated bloodstream infections (CLABSIs), CVAD-related venous thromboses (CRVTs) and –occlusions frequently occur in home parenteral nutrition (HPN) patients. A preventive strategy to decr...detailed

Relevant articles and documents

FUNGICIDAL PENFLUFEN MIXTURES

The invention relates to mixtures comprising penflufen, to the use of these mixtures for protecting industrial materials and to a method for treating industrial materials with the penflufen mixtures.

PROCESS FOR THE PREPARATION OF TAUROLIDINE AND ITS INTERMEDIATES THEREOF

The present invention relates to a process for the preparation of substantially pure Taurolidine.

PROCESS FOR THE PREPARATION OF TAUROLIDINE AND ITS INTERMEDIATES THEREOF

The present invention relates to a process for the preparation of substantially pure Taurolidine.

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