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    Tideglusib

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
    $ API Ref.Price (USD/KG) : 25,173Xls

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    2D Structure
    Also known as: 865854-05-3, Np031112, Np-12, 4-benzyl-2-(naphthalen-1-yl)-1,2,4-thiadiazolidine-3,5-dione, Tideglusib [inn], Np-031112
    Molecular Formula
    C19H14N2O2S
    Molecular Weight
    334.4  g/mol
    InChI Key
    PMJIHLSCWIDGMD-UHFFFAOYSA-N
    FDA UNII
    Q747Y6TT42
    Tideglusib is under the investigation for the development of treatments for Alzheimer's disease and for progressive supranuclear palsy. It is reported to be a potent anti-inflammatory and neuroprotective that is a non-ATP competitive inhibitor of glycogen synthase kinase 3 (GSK-3). Tideglusib is being developed by the Spanish pharmaceutic company Zeltia group and its current status is withdrawn for the treatment of Alzheimer's disease as of 2012.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-benzyl-2-naphthalen-1-yl-1,2,4-thiadiazolidine-3,5-dione
    2.1.2 InChI
    InChI=1S/C19H14N2O2S/c22-18-20(13-14-7-2-1-3-8-14)19(23)24-21(18)17-12-6-10-15-9-4-5-11-16(15)17/h1-12H,13H2
    2.1.3 InChI Key
    PMJIHLSCWIDGMD-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC=C(C=C1)CN2C(=O)N(SC2=O)C3=CC=CC4=CC=CC=C43
    2.2 Other Identifiers
    2.2.1 UNII
    Q747Y6TT42
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-benzyl-2-(naphthalene-1-yl)-1,2,4-thiadiazolidine-3,5-dione

    2. Np 031112

    3. Np-031112

    4. Np-12 Compound

    5. Np031112

    6. Np12 Compound

    2.3.2 Depositor-Supplied Synonyms

    1. 865854-05-3

    2. Np031112

    3. Np-12

    4. 4-benzyl-2-(naphthalen-1-yl)-1,2,4-thiadiazolidine-3,5-dione

    5. Tideglusib [inn]

    6. Np-031112

    7. Np 031112

    8. 4-benzyl-2-naphthalen-1-yl-1,2,4-thiadiazolidine-3,5-dione

    9. Q747y6tt42

    10. 1,2,4-thiadiazolidine-3,5-dione, 2-(1-naphthalenyl)-4-(phenylmethyl)-

    11. 2-(1-naphthalenyl)-4-(phenylmethyl)-1,2,4-thiadiazolidine-3,5-dione

    12. Tideglusibum

    13. Zentylor

    14. Nypta

    15. Unii-q747y6tt42

    16. Tideglusib [who-dd]

    17. Tideglusib(np-031112)

    18. Schembl676929

    19. Gtpl6929

    20. Chembl3545157

    21. Tideglusib, >=98% (hplc)

    22. Dtxsid90235682

    23. Ex-a600

    24. Chebi:147398

    25. Hms3673g17

    26. Hms3744e05

    27. Hms3884j18

    28. 4-benzyl-2-(naphthalen-1-yl)-(1,2,4)thiadiazolidine-3,5-dione

    29. Bcp06016

    30. Tideglusib,cas:865854-05-3

    31. Bdbm50166940

    32. Mfcd18633296

    33. Nsc800950

    34. S2823

    35. Zinc13985228

    36. Akos025149085

    37. Ccg-267855

    38. Cs-0613

    39. Db12129

    40. Nsc-800950

    41. Sb19268

    42. Tideglusib (np031112, Np-12)

    43. Ncgc00386380-06

    44. Ac-31056

    45. As-56156

    46. Da-41071

    47. Hy-14872

    48. Ft-0700382

    49. A857027

    50. J-514478

    51. Q10382411

    52. 4-benzyl-2-(a-naphtyl)-1,2,4-thiadiazolidine-3,5-dione

    53. 4-benzyl-2-(a-naphthyl)-1,2,4-thiadiazolidine-3,5-dione

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 334.4 g/mol
    Molecular Formula C19H14N2O2S
    XLogP34.3
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count3
    Exact Mass334.07759887 g/mol
    Monoisotopic Mass334.07759887 g/mol
    Topological Polar Surface Area65.9 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity492
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Tideglusib was initially formulated for the treatment of Alzheimer and progressive supranuclear palsy. The raising interest for the use of tideglusib comes from the significant upregulation of GSK-3 in the brain in patients with Alzheimer disease. Its function as a degradant of -catenin, was also important, as it prevents the transcription of cell survival genes. All these factors have directed current research towards this kinase as a potential target. Alzheimer disease is the most prevalent form of dementia. The most accepted hypothesis to explain this disease is related to the presence of amyloid , which triggers a cascade that will alter the Tau protein and provoke synaptic dysfunction and neuronal death. GSK-3 importance in the tissue repair pathway has also pointed out a novel application for tideglusib. Thus, it is also under the research for the natural repair treatment of deep caries lesions.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    It is reported that tideglusib administration inhibits the activation of astrocytes and microglial cells, thus it presented a neuroprotective effect. It is known as well that the inactivation of GSK-3 protects against excitotoxicity. In pre-clinical trials, there have been reports of decrease Tau hyperphosphorylation, lower brain amyloid plaque load, learning and memory enhancement, prevention of neuronal loss and significant increases of the insulin growth factor 1 which is a potent neurotrophic peptide with therapeutic value.The reports in clinical trials have shown a trend in cognition increase of Alzheimer patients treated for 24 weeks.

    5.2 Mechanism of Action

    GSK-3 is a proline/serine protein kinase that is ubiquitously expressed and involved in many cellular signaling pathways. From all its diverse functions, it plays a key role in Alzheimer's disease. This role is related to its link with -amyloid and tau pathology. It has been suggested that aberrant Wnt or insulin signaling results in increased GSK-3 function. This kinase acts on -secretase producing the hyperphosphorylation of tau, the formation of neurofibrillary tangles and senile plaques. Tideglusib inhibits GSK-3 irreversibly by presenting a non-competitive inhibition pattern with respect to ATP. The binding of tideglusib seems to directly relate to the motif containing Cys199.