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Ibudilast

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Chemistry

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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

Ibudilast

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 Formula	C₁₄H₁₈N₂O
Molecular Weight	230.31 g/mol
XLogP3	3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Exact Mass	230.141913202 g/mol
Monoisotopic Mass	230.141913202 g/mol
Topological Polar Surface Area	34.4 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	288
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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