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Oxibendazole

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Chemistry

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Also known as: 20559-55-1, Loditac, Filaribits plus, Anthelcide eq, Oxibendazolo, Sk&f 30310

Molecular Formula

C₁₂H₁₅N₃O₃

Molecular Weight

249.27 g/mol

InChI Key

RAOCRURYZCVHMG-UHFFFAOYSA-N

FDA UNII

022N12KJ0X

Oxibendazole is a polymerase inhibitor in phase III trials for the treatment of helminth intestinal infections.

1 2D Structure

Oxibendazole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl N-(6-propoxy-1H-benzimidazol-2-yl)carbamate

2.1.2 InChI

InChI=1S/C12H15N3O3/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)

2.1.3 InChI Key

RAOCRURYZCVHMG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCOC1=CC2=C(C=C1)N=C(N2)NC(=O)OC

2.2 Other Identifiers

2.2.1 UNII

022N12KJ0X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Methyl 5-n-propoxy-2-benzimidazolecarbamate

2.3.2 Depositor-Supplied Synonyms

1. 20559-55-1

2. Loditac

3. Filaribits Plus

4. Anthelcide Eq

5. Oxibendazolo

6. Sk&f 30310

7. Methyl 5-propoxy-2-benzimidazolecarbamate

8. Methyl N-(6-propoxy-1h-benzimidazol-2-yl)carbamate

9. Methyl (5-propoxy-1h-benzo[d]imidazol-2-yl)carbamate

10. Methyl 5-n-propoxy-2-benzimidazole Carbamate

11. Nsc-758459

12. 5-propoxy-2-benzimidazolecarbamic Acid Methyl Ester

13. Mls000069646

14. 2-benzimidazolecarbamic Acid, 5-propoxy-, Methyl Ester

15. Carbamic Acid, (5-propoxy-1h-benzimidazol-2-yl)-, Methyl Ester

16. 022n12kj0x

17. Methyl (5-propoxy-1h-benzimidazol-2-yl)carbamate

18. Methyl N-(5-propoxy-1h-benzimidazol-2-yl)carbamate

19. Mfcd00133728

20. Sk&f-30310

21. Ncgc00018238-04

22. (5-propoxy-1h-benzimidazol-2-yl)carbamic Acid Methyl Ester

23. Smr000058208

24. Carbamic Acid, N-(6-propoxy-1h-benzimidazol-2-yl)-, Methyl Ester

25. Oxibendazole 100 Microg/ml In Acetonitrile

26. Dsstox_cid_25625

27. Dsstox_rid_81010

28. Dsstox_gsid_45625

29. Oxibendazolum

30. Oxibendazolum [inn-latin]

31. Oxibendazolo [inn-spanish]

32. Aj119,(+)

33. Cas-20559-55-1

34. Einecs 243-877-7

35. Skf 30310

36. Oxybendazole

37. Unii-022n12kj0x

38. Oxibendazole [usan:inn:ban]

39. N-(2-(5-propoxybenzimidazolyl)) Methyl Carbamate

40. Anthelcide Eq (tn)

41. Oxibendazole, ~98%

42. Spectrum_001699

43. N-(propoxy-5, Benzimidazolyl)-2, Carbamate De Methyle [french]

44. Spectrum2_001556

45. Spectrum3_001951

46. Spectrum4_000836

47. Spectrum5_001219

48. Oxibendazole [mi]

49. Oxibendazole (usan/inn)

50. Oxibendazole [inn]

51. Oxibendazole [usan]

52. Cid_4622

53. Bspbio_003551

54. Kbiogr_001411

55. Kbioss_002179

56. Oxibendazole [mart.]

57. Mls006011733

58. Divk1c_000096

59. Schembl168101

60. Spectrum1503373

61. Spbio_001432

62. Chembl1087630

63. Dtxsid5045625

64. N-(propoxy-5, Benzimidazolyl)-2, Carbamate De Methyle

65. Bdbm31048

66. Chebi:92907

67. Hms500e18

68. Kbio1_000096

69. Kbio2_002179

70. Kbio2_004747

71. Kbio2_007315

72. Kbio3_002864

73. Oxibendazole [green Book]

74. Ninds_000096

75. Hms1922a22

76. Hms2090f21

77. Hms2094m09

78. Hms3713j18

79. Pharmakon1600-01503373

80. Hy-b0299

81. Zinc4685859

82. Tox21_110844

83. Ccg-39334

84. Nsc758459

85. S1851

86. Stl301145

87. Akos015895323

88. Tox21_110844_1

89. Ac-8714

90. Ccg-220608

91. Db04910

92. Nsc 758459

93. Idi1_000096

94. Oxibendazole 100 Microg/ml In Methanol

95. Ncgc00018238-01

96. Ncgc00018238-02

97. Ncgc00018238-03

98. Ncgc00018238-05

99. Ncgc00018238-06

100. Ncgc00018238-07

101. Ncgc00018238-08

102. Ncgc00018238-09

103. Ncgc00023557-03

104. Ncgc00023557-04

105. Ncgc00023557-05

106. As-12166

107. Sy067010

108. Db-045281

109. 5-propoxy-2-(carbomethoxyamino)benzimidazole

110. Albendazole Impurity I [ep Impurity]

111. Ft-0630464

112. O0499

113. C73898

114. D05293

115. Methyl 5-propoxy-1h-benzimidazol-2-ylcarbamate

116. Ab00052350-06

117. Ab00052350_07

118. Ab00052350_08

119. Oxibendazole, Vetranal(tm), Analytical Standard

120. 559o551

121. A814696

122. Aj-119/34637010

123. Sr-01000000182

124. Sr-05000002065

125. Q7115623

126. Sr-01000000182-2

127. Sr-05000002065-1

128. W-107609

129. Brd-k52075715-001-02-6

130. Brd-k52075715-001-03-4

131. Brd-k84514357-001-02-9

132. Methyl (6-propoxy-1h-benzo[d]imidazol-2-yl)carbamate

133. N-(6-propoxy-1h-benzimidazol-2-yl)carbamic Acid Methyl Ester

134. Oxibendazole, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₅N₃O₃
Molecular Weight	249.27 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	249.11134135 g/mol
Monoisotopic Mass	249.11134135 g/mol
Topological Polar Surface Area	76.2 Å²
Heavy Atom Count	18
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

Investigated for use/treatment in infectious and parasitic disease (unspecified) and pediatric indications.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anthelmintics

Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)

5.2 Metabolism/Metabolites

Hepatic

5.3 Mechanism of Action

Oxibendazole causes degenerative alterations in the tegument and intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. The loss of the cytoplasmic microtubules leads to impaired uptake of glucose by the larval and adult stages of the susceptible parasites, and depletes their glycogen stores. Degenerative changes in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP), which is the energy required for the survival of the helminth. Due to diminished energy production, the parasite is immobilized and eventually dies.

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