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Benznidazole

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53 Fillers, Diluents & Binders
24 Direct Compression
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13 Co-Processed Excipients
11 Granulation
11 Thickeners and Stabilizers
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5 Controlled & Modified Release
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2 Rheology Modifiers
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Synopsis

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Chemistry

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Also known as: 22994-85-0, Radanil, Benznidazol, Benzonidazole, Benzonidazol, Benznidazolum

Molecular Formula

C₁₂H₁₂N₄O₃

Molecular Weight

260.25 g/mol

InChI Key

CULUWZNBISUWAS-UHFFFAOYSA-N

FDA UNII

YC42NRJ1ZD

Benznidazole is a nitroimidazole derivative having an antiprotozoal activity by interfering with parasite protein biosynthesis, influencing cytokines production and stimulating host phagocytosis. (NCI)

1 2D Structure

Benznidazole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-benzyl-2-(2-nitroimidazol-1-yl)acetamide

2.1.2 InChI

InChI=1S/C12H12N4O3/c17-11(14-8-10-4-2-1-3-5-10)9-15-7-6-13-12(15)16(18)19/h1-7H,8-9H2,(H,14,17)

2.1.3 InChI Key

CULUWZNBISUWAS-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)CNC(=O)CN2C=CN=C2[N+](=O)[O-]

2.2 Other Identifiers

2.2.1 UNII

YC42NRJ1ZD

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-nitroimidazole Benznidazole

2. Benzonidazole

3. Radanil

4. Ro 7-1051

2.3.2 Depositor-Supplied Synonyms

1. 22994-85-0

2. Radanil

3. Benznidazol

4. Benzonidazole

5. Benzonidazol

6. Benznidazolum

7. Rochagan

8. Ro 07-1051

9. N-benzyl-2-(2-nitroimidazol-1-yl)acetamide

10. 1h-imidazole-1-acetamide, 2-nitro-n-(phenylmethyl)-

11. N-benzyl-2-(2-nitro-1h-imidazol-1-yl)acetamide

12. N-benzyl-2-nitroimidazole-1-acetamide

13. N-benzyl-2-nitro-1h-imidazole-1-acetamide

14. N-benzyl-2-nitroimidazol-1-yl-acetamide

15. 2-nitro-n-(phenylmethyl)-1h-imidazole-1-acetamide

16. Ro 71051

17. Imidazole-1-acetamide, N-benzyl-2-nitro-

18. Yc42nrj1zd

19. Chembl110

20. Nsc-299972

21. Ro-7-1051

22. Mmv688773

23. Nsc299972

24. Ncgc00166238-01

25. Ro 07-1051;ro 71051

26. Ro-07-1051

27. Dsstox_cid_26570

28. Dsstox_rid_81729

29. Dsstox_gsid_46570

30. Benznidazole [inn]

31. Benznidazol [inn-spanish]

32. Benznidazolum [inn-latin]

33. Smr000857153

34. Nsc 299972

35. Cas-22994-85-0

36. Ccris 2200

37. Sr-01000841264

38. Unii-yc42nrj1zd

39. N-benzyl-2-nitro-1-imidazoleacetamide

40. Brn 0551486

41. Ragonil

42. Acetamide, N-benzyl-2-(nitroimidazol-1-yl)-

43. Benznidazole (tn)

44. Rochagan (tn)

45. Radanil (tn)

46. Benznidazole [mi]

47. Benznidazole (usan/inn)

48. Benznidazole [usan:inn]

49. Benznidazole [usan]

50. Schembl45081

51. Benznidazole [mart.]

52. Mls001332409

53. Mls001332410

54. Mls001360496

55. Benznidazole [who-dd]

56. Benznidazole [who-ip]

57. Dtxsid9046570

58. Schembl22493029

59. Zinc56949

60. Chebi:133833

61. Benznidazole [orange Book]

62. Hms2233g13

63. Hms3369c11

64. Hy-b1548

65. Tox21_112364

66. Bdbm50089916

67. Benznidazolum [who-ip Latin]

68. Mfcd00243089

69. S3741

70. Akos015916722

71. Akos024283499

72. Tox21_112364_1

73. Ccg-267054

74. Db11989

75. Ncgc00166238-02

76. As-68694

77. Cs-0013411

78. Ft-0662547

79. Benznidazol (ro 07-1051; Ro 71051)

80. C74184

81. D02489

82. N-benzyl-2-(2-nitro-imidazol-1-yl)-acetamide

83. N-benzyl-2-(2-nitro-1himidazol-1-yl)acetamide

84. A912716

85. N-benzyl-2-(2-nitro-1h-imidazol-5-yl)acetamide

86. N-benzyl-2-nitro-1h-imidazole-1-acetamide, 97%

87. Q425300

88. 2-(2-nitroimidazol-1-yl)-n-(phenylmethyl)acetamide

89. J-014932

90. Sr-01000841264-3

91. Sr-01000841264-4

92. 1h-imidazole-1-acetamide,2-nitro-n-(phenylmethyl)-

93. Brd-k56156805-001-05-4

94. 1h-imidazole-1-acetamide, 2-nitro-n-(phenylmethyl)- [

95. N-benzyl-2-(2-nitro-imidazol-1-yl)-acetamide (benznidazole)

96. Pyridinium,1-dodecyl-2-[(hydroxyimino)methyl]-,iodide(1:1)

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₂N₄O₃
Molecular Weight	260.25 g/mol
XLogP3	0.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	260.09094026 g/mol
Monoisotopic Mass	260.09094026 g/mol
Topological Polar Surface Area	92.7 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	325
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 use in the treatment of Chagas disease in children 2-12 years of age.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Benznidazole is a trypanocidal agent which kills the causative organism in Chagas disease, *Trypanosoma cruzi*.

5.2 MeSH Pharmacological Classification

Mutagens

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)

Trypanocidal Agents

Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA. (See all compounds classified as Trypanocidal 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.)

5.3 ATC Code

P - Antiparasitic products, insecticides and repellents

P01 - Antiprotozoals

P01C - Agents against leishmaniasis and trypanosomiasis

P01CA - Nitroimidazole derivatives

P01CA02 - Benznidazole

5.4 Absorption, Distribution and Excretion

Absorption

Benznidazole has a bioavailability of 91.7% and a Tmax of 2.93 h.

Route of Elimination

The metabolites of benznidazole appear to be primarily exreted in the urine.

Volume of Distribution

The apparent volume of distribution is 39.19 L.

Clearance

The apparent oral clearance is 2.04 L/h.

5.5 Metabolism/Metabolites

Benznidazole is metabolized by nitroreductases in *Trypanosoma cruzi* and by cytochrome P450 enzymes.

5.6 Biological Half-Life

The half life of elimination is 13.27 h.

5.7 Mechanism of Action

Benznidazole is thought to be reduced to various electrophilic metabolites by nitroreductases present in *Trypanosoma cruzi*. These metabolites likely bind to proteins, lipids, DNA, and RNA resulting in damage to these macromolecules. Benznidazole has been found to increase trypanosomal death through interferon- which is likely present in increased amounts due to inflammation caused by macromolecule damage. DNA in parasites affected by benznidazole has been found to undergo extensive unpacking with overexpression of DNA repair proteins supporting the idea of DNA damage contributing to the mechanism of the drug.

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