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    Taurolidine

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    2D Structure
    Also known as: 19388-87-5, Taurolidin, Taurolin, Cyclo-taurolidine, (cyclo)-taurolidine, 4-[(1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide
    Molecular Formula
    C7H16N4O4S2
    Molecular Weight
    284.4  g/mol
    InChI Key
    AJKIRUJIDFJUKJ-UHFFFAOYSA-N
    FDA UNII
    8OBZ1M4V3V
    Taurolidine is a synthetic broad-spectrum antibiotic with antibacterial, anticoagulant and potential antiangiogenic activities. Taurolidine, derived from the amino acid taurine, binds to and neutralizes bacterial exotoxins and endotoxins, or lipopolysaccharides (LPS). Taurolidine binding to LPS prevents bacterial adherence to host epithelial cells, thereby prevents bacterial invasion of uninfected host cells. Although the mechanism underlying its antineoplastic activity has not been fully elucidated, it may be related to this agent's anti-adherence property. In addition, taurolidine also promotes apoptosis by inducing various apoptotic factors and suppresses the production of vascular endothelial growth factor (VEGF), a protein that plays an important role in angiogenesis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[(1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide
    2.1.2 InChI
    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
    2.1.3 InChI Key
    AJKIRUJIDFJUKJ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CS(=O)(=O)NCN1CN2CCS(=O)(=O)NC2
    2.2 Other Identifiers
    2.2.1 UNII
    8OBZ1M4V3V
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4,4'-methylenebis-(tetrahydro-1,2,4-thiadiazine- 1,1-dioxide)

    2. Bis(1,1-dioxo-perhydro-1,2,4-thiadiazinyl-4)methane

    3. Bis- (1,1-dioxoperhydro-1,2,4-thiadiazinyl-4)methane

    4. Tauroflex

    5. Taurolin

    6. Tauroline

    2.3.2 Depositor-Supplied Synonyms

    1. 19388-87-5

    2. Taurolidin

    3. Taurolin

    4. Cyclo-taurolidine

    5. (cyclo)-taurolidine

    6. 4-[(1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide

    7. 8obz1m4v3v

    8. 4,4'-methylenebis(1,2,4-thiadiazinane 1,1-dioxide)

    9. Tauroline

    10. 4,4'-methylenebis(tetrahydro-1,2,4-thiadiazine 1,1-dioxide)

    11. Taurolidine (inn)

    12. W-3100m

    13. Taurolidine [inn]

    14. Taurolidina

    15. Taurolidinum

    16. Taurolidinum [inn-latin]

    17. Taurolidina [inn-spanish]

    18. Taurolidine [inn:ban]

    19. Einecs 243-016-5

    20. Unii-8obz1m4v3v

    21. Taurolidine [mi]

    22. Taurolidine [mart.]

    23. Schembl65313

    24. Taurolidine [who-dd]

    25. Chembl2105420

    26. Dtxsid00173001

    27. Chebi:135173

    28. Amy28822

    29. S4885

    30. Taurolidine, >97% (nmr), Powder

    31. Zinc19322537

    32. Taurolock Component Taurolidine

    33. 2h-1,2,4-thiadiazine, 4,4'-methylenebis[tetrahydro-, 1,1,1',1'-tetraoxide

    34. Akos015896472

    35. Ac-1423

    36. Ccg-267310

    37. Cs-w012238

    38. Db12473

    39. Hy-w011522

    40. Ls-13376

    41. Ft-0617113

    42. T3980

    43. D07146

    44. D78247

    45. 388t875

    46. A813672

    47. Sr-01000872621

    48. Q3981568

    49. Sr-01000872621-2

    50. W-107711

    51. 4,4'-methylenebis(1,2,4-thiadiazinane) 1,1,1',1'-tetraoxide

    52. 4,4'-methylene-bis(tetrahydro-1,2,4-thiadiazine-1,1-dioxide)

    53. 4-[(1,1-dioxido-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide #

    2.4 Create Date
    2005-03-27
    3 Chemical and Physical Properties
    Molecular Weight 284.4 g/mol
    Molecular Formula C7H16N4O4S2
    XLogP3-1.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count2
    Exact Mass284.06129735 g/mol
    Monoisotopic Mass284.06129735 g/mol
    Topological Polar Surface Area116 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity419
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    Anti-Infective Agents

    Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

    Anti-Infective Agents, Local

    Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)

    4.2 ATC Code

    B - Blood and blood forming organs

    B05 - Blood substitutes and perfusion solutions

    B05C - Irrigating solutions

    B05CA - Antiinfectives

    B05CA05 - Taurolidine