An antibiotic with anti-neoplastic actions
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Taurolidine

Item No. 15374

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4,4'-methylenebis(tetrahydro-1,2H,4-thiadiazine) 1,1,1',1'-tetraoxide
CAS Number
19388-87-5
Molecular Formula
C7H16N4O4S2
Formula Weight
284.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/ml
SMILES
O=S1(CCN(CN2CNS(CC2)(=O)=O)CN1)=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $36

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    10 mg

    $61

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    25 mg

    $128

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    50 mg

    $203

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    Cayman Chemical
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    Product Description

    Taurolidine is a synthetic taurine analog with antimicrobial and anti-neoplastic actions. It displays broad bactericidal and fungicidal activity.1 Taurolidine and its metabolites mimic mannose by binding to the extracellular wall of bacteria, blocking adherence to epithelial and fibroblast cells.2 In addition to modulating immunoregulatory systems, taurolidine induces autophagy, apoptosis, and necrosis in human cancer cells.1,3,4,5 It produces cell death in malignant mesothelioma cells by oxidative stress in concert with inhibition of Akt signaling.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Calabresi, P., Goulette, F.A., and Darnowski, J.W. Taurolidine: Cytotoxic and mechanistic evaluation of a novel antineoplastic agent. Cancer Res. 61(18), 6816-6821 (2001).

    2. Caruso, F., Darnowski, J.W., Opazo, C., et al. Taurolidine antiadhesive properties on interaction with E. coli; its transformation in biological environment and interaction with bacteria cell wall. PLoS One 5(1), e8927 (2010).

    3. Watson, R.W., Redmond, H.P., McCarthy, J., et al. Taurolidine, an antilipopolysaccharide agent, has immunoregulatory properties that are mediated by the amino acid taurine. J. Leukoc. Biol. 58(3), 299-306 (1995).

    4. Chromik, A.M., Daigeler, A., Bulut, D., et al. Comparative analysis of cell death induction by taurolidine in different malignant human cancer cell lines. J. Exp. Clin. Cancer Res. 29(1), 21 (2010).

    5. Stendel, R., Biefer, H.R., Dékány, G.M., et al. The antibacterial substance taurolidine exhibits anti-neoplastic action based on a mixed type of programmed cell death. Autophagy 5(2), 194-210 (2009).

    6. Aceto, N., Bertino, P., Barbone, D., et al. Taurolidine and oxidative stress: A rationale for local treatment of mesothelioma. Eur. Respir .J. 34(6), 1399-1407 (2009).