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    Binimetinib

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 606143-89-9, Mek162, Arry-162, Mektovi, Arry-438162, Mek-162
    Molecular Formula
    C17H15BrF2N4O3
    Molecular Weight
    441.2  g/mol
    InChI Key
    ACWZRVQXLIRSDF-UHFFFAOYSA-N
    FDA UNII
    181R97MR71
    Binimetinib is an orally available inhibitor of mitogen-activated protein kinase kinase 1 and 2 (MEK1/2) with potential antineoplastic activity. Binimetinib, noncompetitive with ATP, binds to and inhibits the activity of MEK1/2. Inhibition of MEK1/2 prevents the activation of MEK1/2 dependent effector proteins and transcription factors, which may result in the inhibition of growth factor-mediated cell signaling. This may eventually lead to an inhibition of tumor cell proliferation and an inhibition in production of various inflammatory cytokines including interleukin-1, -6 and tumor necrosis factor. MEK1/2 are dual-specificity threonine/tyrosine kinases that play key roles in the activation of the RAS/RAF/MEK/ERK pathway and are often upregulated in a variety of tumor cell types.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6-(4-bromo-2-fluoroanilino)-7-fluoro-N-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide
    2.1.2 InChI
    InChI=1S/C17H15BrF2N4O3/c1-24-8-21-16-13(24)7-10(17(26)23-27-5-4-25)15(14(16)20)22-12-3-2-9(18)6-11(12)19/h2-3,6-8,22,25H,4-5H2,1H3,(H,23,26)
    2.1.3 InChI Key
    ACWZRVQXLIRSDF-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1C=NC2=C1C=C(C(=C2F)NC3=C(C=C(C=C3)Br)F)C(=O)NOCCO
    2.2 Other Identifiers
    2.2.1 UNII
    181R97MR71
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Mek162

    2. Mektovi

    2.3.2 Depositor-Supplied Synonyms

    1. 606143-89-9

    2. Mek162

    3. Arry-162

    4. Mektovi

    5. Arry-438162

    6. Mek-162

    7. 5-[(4-bromo-2-fluorophenyl)amino]-4-fluoro-n-(2-hydroxyethoxy)-1-methyl-1h-benzimidazole-6-carboxamide

    8. Arry 438162

    9. Arry 162

    10. Binimetinib (mek-162)

    11. Nvp-mek162

    12. Mek162 (arry-162, Arry-438162)

    13. Mfcd22124525

    14. Binimetinib (mek162, Arry-162, Arry-438162)

    15. 181r97mr71

    16. 6-(4-bromo-2-fluoroanilino)-7-fluoro-n-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide

    17. 5-((4-bromo-2-fluorophenyl)amino)-4-fluoro-n-(2-hydroxyethoxy)-1-methyl-1h-benzo[d]imidazole-6-carboxamide

    18. 5-((4-bromo-2-fluorophenyl)amino)-4-fluoro-n-(2-hydroxyethoxy)-1-methyl-1h-benzo[d]imidazole-6-carboxamide.

    19. 5-(4-bromo-2-fluoroanilino)-4-fluoro-n-(2-hydroxyethoxy)-1-methyl-1h-benzimidazole-6-carboxamide

    20. Binimetinib [usan:inn]

    21. Binimetinibum

    22. Unii-181r97mr71

    23. 5-((4-bromo-2-fluorophenyl)amino)-4-fluoro-n-(2-hydroxyethoxy)-1-methyl-1h-benzimidazole-6-carboxamide

    24. 5-(4-bromo-2-fluorophenylamino)-4-fluoro-n-(2-hydroxyethoxy)-1-methyl-1h-benzo(d)imidazole-6-carboxamide

    25. 5-(4-bromo-2-fluorophenylamino)-4-fluoro-n-(2-hydroxyethoxy)-1-methyl-1h-benzo[d]imidazole-6-carboxamide

    26. Mektovi (tn)

    27. Arry-162; Arry-438162; Mek 162; Arry 162; Arry 438162

    28. Binimetinib; Mek162

    29. Mek162(binimetinib)

    30. Binimetinib [mi]

    31. Binimetinib (mek162)

    32. Binimetinib [inn]

    33. Binimetinib [jan]

    34. Binimetinib (jan/usan)

    35. Binimetinib [usan]

    36. Binimetinib [who-dd]

    37. Mls006011180

    38. Schembl570088

    39. Gtpl7921

    40. Chembl3187723

    41. Amy9056

    42. Binimetinib [orange Book]

    43. Dtxsid70209422

    44. Arry-162,mek-162

    45. Chebi:145371

    46. Bdbm520649

    47. Hms3652j14

    48. Hms3747g09

    49. Bcp06780

    50. Ex-a1024

    51. Nsc764042

    52. Nsc788187

    53. Nsc799361

    54. S7007

    55. Zinc38460704

    56. Akos026750517

    57. Ccg-269133

    58. Cs-0627

    59. Db11967

    60. Nsc-764042

    61. Nsc-788187

    62. Nsc-799361

    63. Sb16501

    64. Ncgc00345804-01

    65. Ncgc00345804-10

    66. 1073666-70-2

    67. 5-[(4-bromo-2-fluorophenyl)amino]-4-fluoro-n-(2-hydroxyethoxy)-1-methylbenzimidazole-6-carboxamide

    68. 6-(4-bromo-2-fluorophenylamino)-7-fluoro-n-(2-hydroxyethoxy)-3-methyl-3h-benzo[d]imidazole-5-carboxamide

    69. Ac-29023

    70. As-16706

    71. Da-35030

    72. Hy-15202

    73. Smr004702949

    74. Sy284756

    75. Cas:606143-89-9;mek162

    76. Ft-0697088

    77. Sw219910-1

    78. D10604

    79. Binimetinib;mek-162; Arry-162;arry-438162

    80. J-516581

    81. Q19903515

    82. Us11147816, Binimetinib (arry-162, Arry-438162)

    83. 1h-benzimidazole-6-carboxamide, 5-((4-bromo-2-fluorophenyl)amino)-4-fluoro-n-(2-hydroxyethoxy)-1-methyl-

    84. 5-((4-bromo-2-fluorophenylamino)-4-fluoro-n-(2-hydroxyethoxy)-1-methyl-1h-benzo (d) Imidazole-6-carboxamide

    85. 5-[(4-bromo-2-fluorophenyl)amino]-4-fluoro-n-(2-hydroxyethoxy)-1-methyl-1h-1,3-benzodiazole-6-carboxamide

    86. 5-[(4-bromo-2-fluorophenyl)amino]-4-fluoro-n-(2-hydroxyethoxy)-1-methyl-1h-benzimidazole-6-carboxami

    87. 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3h-benzoimidazole-5-carboxylic Acid (2-hydroxyethyoxy)-amide

    88. 6-[(4-bromo-2-fluorophenyl)amino]-7-fluoro-n-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide

    89. N-(2-hydroxyethoxy)-4-fluoro-5-(2-fluoro-4-bromophenylamino)-1-methyl-1h-benzoimidazole-6-carboxamide

    90. Qo7

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 441.2 g/mol
    Molecular Formula C17H15BrF2N4O3
    XLogP33.1
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count6
    Exact Mass440.02956 g/mol
    Monoisotopic Mass440.02956 g/mol
    Topological Polar Surface Area88.4 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity521
    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

    On June 27, 2018, the Food and Drug Administration approved encorafenib and binimetinib in combination patients with unresectable or metastatic melanoma with a BRAF V600E or V600K mutation, as detected by an FDA-approved test.

    Binimetinib in combination with encorafenib is indicated for the treatment of adult patients with unresectable or metastatic melanoma with a BRAF V600 mutation.

    Treatment of colorectal carcinoma

    Treatment of melanoma

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Binimetinib is a MEK inhibitor. MEK is an enzyme that regulates the biosynthesis of the inflammatory cytokines TNF, IL-6 and IL-1. MEK inhibitors interfere with these biosynthetic processes. It is a chemotherapeutic agent that has anti-tumor activity,.

    5.2 ATC Code

    L01EE03

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01E - Protein kinase inhibitors

    L01EE - Mitogen-activated protein kinase (mek) inhibitors

    L01EE03 - Binimetinib

    5.3 Absorption, Distribution and Excretion

    Absorption

    Following oral administration in a pharmacokinetic study, at least 50% of the binimetinib dose was absorbed with a median time to maximum concentration (Tmax) of 1.6 hours. The administration of a single dose of MEKTOVI 45 mg with a high-fat, high-calorie meal (consisting of approximately 150 calories from protein, 350 calories from carbohydrate, and 500 calories from fat) in healthy subjects had no effect on binimetinib exposure.

    Route of Elimination

    Following a single oral dose of 45 mg radiolabeled binimetinib in healthy subjects, 62% (32% unchanged) of the administered dose was recovered in the feces while 31% (6.5% unchanged) was recovered in the urine.

    Volume of Distribution

    The geometric mean (CV%) of apparent volume of distribution of binimetinib is 92 L (45%)

    Clearance

    20.2 L/h (24%)

    5.4 Metabolism/Metabolites

    The primary metabolic pathway is glucuronidation with UGT1A1 contributing up to 61% of the binimetinib metabolism. Other pathways of binimetinib metabolism include N-dealkylation, amide hydrolysis, and loss of ethane-diol from the side chain. The active metabolite M3 produced by CYP1A2 and CYP2C19 represents 8.6% of the binimetinib exposure. Following a single oral dose of 45 mg radiolabeled binimetinib, approximately 60% of the circulating radioactivity AUC in plasma was attributable to binimetinib.

    5.5 Biological Half-Life

    The mean (CV%) terminal half-life (t1/2) of binimetinib is 3.5 hours (28.5%).

    5.6 Mechanism of Action

    Binimetinib, noncompetitive with ATP, binds to and inhibits the activity of MEK1/2. The inhibition of MEK1/2 prevents the activation of MEK1/2-dependent effector proteins and transcription factors. This process can result in the inhibition of growth factor-mediated cell signaling. This may lead to the inhibition of tumor cell proliferation and an inhibition in the production of various inflammatory cytokines including interleukin-1, -6 and tumor necrosis factor. MEK1/2 are themselves threonine and tyrosine kinases that possess a dual specificity. They subsequently contribute critically to the activation of the RAS/RAF/MEK/ERK pathway and are typically upregulated in a number of different tumor cell types.