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    Oxibendazole

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    DIGITAL CONTENT

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    PharmaCompass
    $ API Ref.Price (USD/KG) : 3,360Xls

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    2D Structure
    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

    2D Structure

    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 Weight 249.27 g/mol
    Molecular Formula C12H15N3O3
    XLogP32.4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass249.11134135 g/mol
    Monoisotopic Mass249.11134135 g/mol
    Topological Polar Surface Area76.2 Ų
    Heavy Atom Count18
    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

    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.