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Mizoribine

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Chemistry

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Also known as: 50924-49-7, Bredinin, He-69, Mls000028813, 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-hydroxy-1h-imidazole-4-carboxamide, He 69

Molecular Formula

C₉H₁₃N₃O₆

Molecular Weight

259.22 g/mol

InChI Key

HZQDCMWJEBCWBR-UUOKFMHZSA-N

FDA UNII

4JR41A10VP

Mizoribine has been investigated for the treatment of Rheumatoid Arthritis.

1 2D Structure

Mizoribine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide

2.1.2 InChI

InChI=1S/C9H13N3O6/c10-7(16)4-8(17)12(2-11-4)9-6(15)5(14)3(1-13)18-9/h2-3,5-6,9,13-15,17H,1H2,(H2,10,16)/t3-,5-,6-,9-/m1/s1

2.1.3 InChI Key

HZQDCMWJEBCWBR-UUOKFMHZSA-N

2.1.4 Canonical SMILES

C1=NC(=C(N1C2C(C(C(O2)CO)O)O)O)C(=O)N

2.1.5 Isomeric SMILES

C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)N

2.2 Other Identifiers

2.2.1 UNII

4JR41A10VP

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bredinin

2. Mizoribine 5'-monophosphate

2.3.2 Depositor-Supplied Synonyms

1. 50924-49-7

2. Bredinin

3. He-69

4. Mls000028813

5. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-hydroxy-1h-imidazole-4-carboxamide

6. He 69

7. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide

8. Bredinine

9. 5-hydroxy-1-beta-d-ribofuranosyl-1h-imidazole-4-carboxamide

10. 50524-49-7

11. Smr000058473

12. 5-hydroxy-1-beta-d-ribofuranosylimidazole-4-carboxamide

13. 4jr41a10vp

14. 1h-imidazole-4-carboxamide, 5-hydroxy-1-beta-d-ribofuranosyl-

15. Nsc 289637

16. Nsc-289637

17. Ncgc00094087-01

18. Mizoribinum

19. Mizoribina

20. N'-(beta-d-ribofuranosyl)-5-hydroxyimidazole-4-carboxamide

21. Mizoribine [inn:jan]

22. Dsstox_cid_25777

23. Dsstox_rid_81119

24. Dsstox_gsid_45777

25. Mizoribinum [inn-latin]

26. Mizoribina [inn-spanish]

27. Bredinin (tn)

28. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxy-1h-imidazole-4-carboxamide

29. Cas-50924-49-7

30. Sr-01000075989

31. Brn 4151713

32. Unii-4jr41a10vp

33. 1h-imidazole-4-carboxamide, 5-hydroxy-1-.beta.-d-ribofuranosyl-

34. 4-carbamoyl-1-beta-d-ribofuranosyl-imidazolium-5-olate

35. Anhydro-4-carbamoyl-5-hydroxy-1-beta-d-ribofuranosyl-imidazolium Hydroxide

36. Mfcd00057221

37. Mizoribine(bredinin)

38. Hs-0046

39. Mizoribine (bredinin)

40. Mizoribine Hydrobromide

41. Mizoribine [mi]

42. Mizoribine [inn]

43. Mizoribine [jan]

44. Opera_id_1558

45. Spectrum2_001559

46. Spectrum3_000739

47. Spectrum4_000220

48. Spectrum5_001671

49. Mizoribine (jp17/inn)

50. M 3047

51. Mizoribine [mart.]

52. Schembl7118

53. Mizoribine [who-dd]

54. Lopac0_000745

55. Bspbio_002298

56. Kbiogr_000859

57. Mls001076272

58. Mls006010038

59. Divk1c_000948

60. Spbio_001438

61. Chembl245019

62. Cid_104762

63. Mizoribine, >=98% (tlc)

64. Dtxsid8045777

65. Bdbm68669

66. Chebi:31858

67. Hms502p10

68. Kbio1_000948

69. Kbio3_001518

70. Ninds_000948

71. Hms2230d04

72. Hms3262e12

73. 50924-49-7 (non-salt)

74. Ex-a2256

75. Zinc3812887

76. Tox21_111242

77. Tox21_500745

78. Ccg-39778

79. Fd9057

80. S1384

81. Akos015994615

82. Tox21_111242_1

83. Ac-5266

84. Bcp9000933

85. Cs-1823

86. Db12617

87. Lp00745

88. Sdccgsbi-0050723.p004

89. Idi1_000948

90. Smp1_000195

91. Ncgc00094087-02

92. Ncgc00094087-03

93. Ncgc00094087-04

94. Ncgc00094087-05

95. Ncgc00261430-01

96. Hy-17470

97. Bcp0726000318

98. Sbi-0050723.p003

99. Eu-0100745

100. M2399

101. A16794

102. D01392

103. Ab00053323_12

104. Ab00053323_13

105. 924m497

106. J-700185

107. Q6884708

108. Sr-01000075989-1

109. Sr-01000075989-4

110. 1-(beta-d-ribofuranosyl)-5-hydroxyimidazole-4-carboxamide

111. 4-carbamoyl-1-(beta-d-ribofuranosyl)-5-oxylatoimidazolium

112. 5-hydroxy-1-b-d-ribofuranosyl-1h-imidazole-4-carboxamide

113. 1h-imidazole-4-carboxamide, 5-hydroxy-1-b-d-ribofuranosyl-

114. 5-hydroxy-1-.beta.-d-ribofuranosylimidazole-4-carboxamide

115. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-oxolanyl]-5-hydroxy-4-imidazolecarboxamide

116. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-hydroxy-imidazole-4-carboxamide

117. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-5-hydroxy-imidazole-4-carboxamide

118. 1-[(2r,3r,4s,5r)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]-5-oxidanyl-imidazole-4-carboxamide

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₃N₃O₆
Molecular Weight	259.22 g/mol
XLogP3	-1.9
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	259.08043514 g/mol
Monoisotopic Mass	259.08043514 g/mol
Topological Polar Surface Area	151 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	329
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

Antimalarials

Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Immunosuppressive Agents

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

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