| Identification | Back Directory | [Name]
Taurolidine | [CAS]
19388-87-5 | [Synonyms]
TauroL
taurolin
Tauroline
Taurolidin
TAUROLIDINE
Taurolidine USP/EP/BP
CAS19388-87-5 Taurolidine
4,4'-Methylenebis(perhydro-1,2,4-thiadiazin 1,1-dioxide)
4,4'-Methylenebis(tetrahydro-2H-1,2,4-thiadiazine 1,1-dioxide)
4,4'-methylenebis[tetrahydro-2h-1,2,4-thiadiazine] 1,1,1',1'-tetraoxide
2H-1,2,4-Thiadiazine, 4,4'-methylenebis[tetrahydro-, 1,1,1',1'-tetraoxide
4-[(1,1-Dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide | [EINECS(EC#)]
243-016-5 | [Molecular Formula]
C7H16N4O4S2 | [MDL Number]
MFCD00865076 | [MOL File]
19388-87-5.mol | [Molecular Weight]
284.356 |
| Chemical Properties | Back Directory | [Melting point ]
154-158° | [Boiling point ]
471.2±55.0 °C(Predicted) | [density ]
1.466±0.06 g/cm3(Predicted) | [storage temp. ]
room temp | [solubility ]
DMSO: >20mg/mL | [form ]
powder | [pka]
11.16±0.20(Predicted) | [color ]
white to off-white | [Stability:]
Unstable in Aqueous Solution | [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 | [InChIKey]
AJKIRUJIDFJUKJ-UHFFFAOYSA-N | [SMILES]
O=S1(=O)CCN(CN1)CN2CCS(=O)(=O)NC2 |
| Hazard Information | Back Directory | [Uses]
Antibiotic with broad activity against aerobic, anaerobic, gram positive and gram negative bacteria, mycobacteria and fungi. Reacts with the cell wall. Has an anti-adherence effect. Inhibits tumor cell growth in vitro and in vivo. Has antitoxic properties by chemical inactivation of endo- and exotoxins. | [Definition]
ChEBI: Taurolidine is a thiadiazinane. | [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. | [Synthesis]
To an aqueous solution of 100 g of sodium taurate sodium succinate, saturated sodium bicarbonate solution was added and the pH was adjusted to 7-8. Subsequently, 50 mL of formaldehyde was added to the reaction system and the reaction was stirred for 4 hours at room temperature. Upon completion of the reaction, the precipitated solid product was collected by filtration and washed several times with deionized water to obtain taurine. After further purification, the target product 4,4'-methylenebis(1,2,4-thiadiazinane 1,1-dioxide) was obtained in about 70% yield and about 98% purity. | [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. |
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