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    Ibudilast

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    2D Structure
    Also known as: 50847-11-5, Ketas, Kc-404, Mn-166, Ibudilastum, Ke tas
    Molecular Formula
    C14H18N2O
    Molecular Weight
    230.31  g/mol
    InChI Key
    ZJVFLBOZORBYFE-UHFFFAOYSA-N
    FDA UNII
    M0TTH61XC5
    Ibudilast is an orally bioavailable inhibitor of cyclic nucleotide phosphodiesterase (PDE), mainly PDE-3, -4, -10, and -11, with anti-(neuro)inflammatory, vasorelaxant, bronchodilator, analgesic, neuroprotective and potential anti-tumor activities. Ibudilast (IBD) is able to cross the blood-brain barrier (BBB). Upon administration, IBD exerts its potential anti-tumor activity against glioblastoma multiforme (GBM) cells by inhibiting PDE-4 and the pro-inflammatory cytokine macrophage migration inhibitory factor (MIF), which results in a decrease in MIF, its receptor CD74, and AKT expression, and attenuates the immunosuppressive properties of monocytic myeloid-derived suppressor cells (MDSCs) and reduces T-regulatory cells (Tregs). This causes GBM cell apoptosis and inhibits GBM cell proliferation. In addition, IBD reduces, through its inhibitory effect on various PDEs, the production of certain pro-inflammatory cytokines, such as interleukin-6 (IL-6), IL- 1beta, leukotriene B4, and tumor necrosis factor-alpha (TNF-a). IBD also upregulates the anti-inflammatory cytokine (IL-10), and promotes the production of neurotrophic factors, such as brain-derived neurotrophic factor (BDNF), nerve growth factor (NGF), and neurotrophin-4 (NT-4). It also blocks toll-like receptor-4 (TLR-4), inhibits nitric oxide (NO) synthesis and reduces the level of reactive oxygen species (ROS). It also prevents platelet aggregation, causes cerebral vasodilation, bronchial smooth muscle relaxation, and improves cerebral blood flow. In addition, IBD attenuates the PDE-mediated activation of glial cells and abrogates PDE-mediated neuroinflammation and neurodegeneration. MIF is secreted by cancer stem cells (CSCs) and is highly expressed within GBM and plays a key role in tumor cell proliferation. Co-expression of MIF and CD74 in GBM is associated with poor patient survival.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-methyl-1-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one
    2.1.2 InChI
    InChI=1S/C14H18N2O/c1-9(2)13-12(14(17)10(3)4)11-7-5-6-8-16(11)15-13/h5-10H,1-4H3
    2.1.3 InChI Key
    ZJVFLBOZORBYFE-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)C1=NN2C=CC=CC2=C1C(=O)C(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    M0TTH61XC5
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(2-isopropylpyrazolo(1,5-a)pyridin-3-yl)-2-methyl-1-propanone

    2. 1-(2-isopropylpyrazolo(1,5-alpha)pyridin-3-yl)-2-methyl-1-propanone

    3. 3-isobutyryl-2-isopropylpyrazolo(1,5-a)pyridine

    4. Av 411

    5. Av-411

    6. Av411

    7. Kc 404

    8. Kc-404

    9. Mn-166

    10. Mn166

    2.3.2 Depositor-Supplied Synonyms

    1. 50847-11-5

    2. Ketas

    3. Kc-404

    4. Mn-166

    5. Ibudilastum

    6. Ke Tas

    7. Ibudilastum [latin]

    8. Av-411

    9. Ibudilast [inn:jan]

    10. Eyevinal

    11. Ketas (tn)

    12. 2-methyl-1-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one

    13. 3-isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine

    14. Unii-m0tth61xc5

    15. 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one

    16. Av411

    17. 3-isobutyryl-2-isopropylpyrazolo(1,5-a)pyridine

    18. Tocris-1694

    19. Lopac-i-0157

    20. 1-propanone, 2-methyl-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-

    21. 2-isopropyl-3-isobutyrylpyrazolo(1,5-a)pyridine

    22. Mfcd00864808

    23. M0tth61xc5

    24. Chembl19449

    25. Kc-404;av-411;mn-166

    26. Ncgc00015542-05

    27. 2-methyl-1-[2-(propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]propan-1-one

    28. 1-propanone, 2-methyl-1-(2-(1-methylethyl)pyrazolo(1,5-a)pyridin-3-yl)-

    29. Dsstox_cid_28933

    30. Dsstox_rid_83199

    31. 2-isopropyl-3-isobutyrylpyrazolo[1,5-a]pyridine

    32. Dsstox_gsid_49007

    33. Ibudilast (jan/inn)

    34. Av 411

    35. Cas-50847-11-5

    36. Sr-01000075927

    37. Brn 0656579

    38. Pinatos

    39. I0157_sigma

    40. 1-(2-isopropylpyrazolo(1,5-a)pyridin-3-yl)-2-methyl-1-propanone

    41. Ibudilast,(s)

    42. Pyrazolo(1,5-a)pyridine, 3-isobutyryl-2-isopropyl-

    43. Ibudilast [inn]

    44. Ibudilast [jan]

    45. Ibudilast [mi]

    46. Ibudilast (jp17/inn)

    47. Ibudilast [mart.]

    48. I 0157

    49. Ibudilast [who-dd]

    50. Lopac0_000599

    51. Schembl30390

    52. 5-24-03-00396 (beilstein Handbook Reference)

    53. Mls000862198

    54. Gtpl7399

    55. Zinc4234

    56. Dtxsid7049007

    57. Chebi:31684

    58. Bcpp000209

    59. Hms2089b21

    60. Hms2233h08

    61. Hms3261h20

    62. Hms3268o11

    63. Hms3374p02

    64. Hms3412b20

    65. Hms3676b20

    66. Hms3715l09

    67. Hms3886m03

    68. Bcp02335

    69. Hy-b0763

    70. Tox21_113503

    71. Tox21_500599

    72. Bdbm50240404

    73. S4837

    74. Ibudilast, >=99% (hplc), Solid

    75. Akos015895123

    76. Tox21_113503_1

    77. Ac-1044

    78. Bcp9000768

    79. Ccg-204688

    80. Db05266

    81. Lp00599

    82. Sb19092

    83. Sdccgsbi-0050581.p002

    84. Ncgc00015542-01

    85. Ncgc00015542-02

    86. Ncgc00015542-03

    87. Ncgc00015542-04

    88. Ncgc00015542-06

    89. Ncgc00015542-07

    90. Ncgc00015542-17

    91. Ncgc00025261-01

    92. Ncgc00025261-02

    93. Ncgc00025261-03

    94. Ncgc00025261-04

    95. Ncgc00261284-01

    96. Smr000326961

    97. Sy051343

    98. Eu-0100599

    99. Ft-0654591

    100. Ft-0670255

    101. I0740

    102. D01385

    103. F20666

    104. Ab00698306-06

    105. 3-isobutyryl-2-isopropyl-pyrazolo(1,5-a)pyridine

    106. 847i115

    107. A828320

    108. H-20256

    109. L003042

    110. Q261167

    111. J-512714

    112. Sr-01000075927-1

    113. Sr-01000075927-3

    114. Sr-01000075927-6

    115. Brd-k16444452-001-03-4

    116. 1-(2-isopropylh-pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one

    117. 1-(2-isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-2-methyl-propan-1-one

    118. 1-(2-isopropyl-pyrazolo[1,5-alpha]pyridin-3-yl)-2-methyl-propan-1-one

    119. 1-(2-isopropylpyrazolo[1,5-alpha]pyridin-3-yl)-2-methylpropan-1-one

    120. 2-methyl-1-(2-propan-2-yl-3-pyrazolo[1,5-a]pyridinyl)-1-propanone

    121. 2-methyl-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanone

    122. (ibudilast)1-(2-isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-2-methyl-propan-1-one

    123. 1-(2-isopropylpyrazolo(1,5-.alpha.)pyridin-3-yl)-2-methyl-1-propanone

    124. 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one (ibudilast)

    125. Avl

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 230.31 g/mol
    Molecular Formula C14H18N2O
    XLogP33
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count3
    Exact Mass230.141913202 g/mol
    Monoisotopic Mass230.141913202 g/mol
    Topological Polar Surface Area34.4 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity288
    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

    For the treatment of multiple sclerosis, asthma, and cerebrovascular disease.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Vasodilator Agents

    Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

    Platelet Aggregation Inhibitors

    Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)

    Bronchodilator Agents

    Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)

    Phosphodiesterase Inhibitors

    Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases. (See all compounds classified as Phosphodiesterase Inhibitors.)

    5.2 ATC Code

    R - Respiratory system

    R03 - Drugs for obstructive airway diseases

    R03D - Other systemic drugs for obstructive airway diseases

    R03DC - Leukotriene receptor antagonists

    R03DC04 - Ibudilast

    5.3 Biological Half-Life

    19 hours

    5.4 Mechanism of Action

    Ibudilast has mechanisms that include anti-inflammatory effects, such as phosphodiesterase inhibition, and neuroprotective effects, such as inhibition of [nitric oxide] synthesis and reduction in reactive oxygen species.