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    Trametinib

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 871700-17-3, Gsk1120212, Mekinist, Gsk-1120212, Jtp 74057, Jtp-74057
    Molecular Formula
    C26H23FIN5O4
    Molecular Weight
    615.4  g/mol
    InChI Key
    LIRYPHYGHXZJBZ-UHFFFAOYSA-N
    FDA UNII
    33E86K87QN
    Trametinib is an orally bioavailable inhibitor of mitogen-activated protein kinase kinase (MAP2K; MAPK/ERK kinase; MEK) 1 and 2, with potential antineoplastic activity. Upon oral administration, trametinib specifically binds to and inhibits MEK 1 and 2, resulting in an inhibition of growth factor-mediated cell signaling and cellular proliferation in various cancers. MEK 1 and 2, dual specificity serine/threonine and tyrosine kinases often upregulated in various cancer cell types, play a key role in the activation of the RAS/RAF/MEK/ERK signaling pathway that regulates cell growth.
    Trametinib is a Kinase Inhibitor. The mechanism of action of trametinib is as a Protein Kinase Inhibitor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[3-[3-cyclopropyl-5-(2-fluoro-4-iodoanilino)-6,8-dimethyl-2,4,7-trioxopyrido[4,3-d]pyrimidin-1-yl]phenyl]acetamide
    2.1.2 InChI
    InChI=1S/C26H23FIN5O4/c1-13-22-21(23(31(3)24(13)35)30-20-10-7-15(28)11-19(20)27)25(36)33(17-8-9-17)26(37)32(22)18-6-4-5-16(12-18)29-14(2)34/h4-7,10-12,17,30H,8-9H2,1-3H3,(H,29,34)
    2.1.3 InChI Key
    LIRYPHYGHXZJBZ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=C2C(=C(N(C1=O)C)NC3=C(C=C(C=C3)I)F)C(=O)N(C(=O)N2C4=CC=CC(=C4)NC(=O)C)C5CC5
    2.2 Other Identifiers
    2.2.1 UNII
    33E86K87QN
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Gsk 1120212

    2. Gsk-1120212

    3. Gsk1120212

    4. Jtp 74057

    5. Jtp-74057

    6. Jtp74057

    2.3.2 Depositor-Supplied Synonyms

    1. 871700-17-3

    2. Gsk1120212

    3. Mekinist

    4. Gsk-1120212

    5. Jtp 74057

    6. Jtp-74057

    7. Gsk 1120212

    8. Trametinib (gsk1120212)

    9. N-[3-[3-cyclopropyl-5-[(2-fluoro-4-iodophenyl)amino]-3,4,6,7-tetrahydro-6,8-dimethyl-2,4,7-trioxopyrido[4,3-d]pyrimidin-1(2h)-yl]phenyl]acetamide

    10. Gsk212

    11. Tmt212

    12. Trametinib [usan]

    13. Chebi:75998

    14. Tmt-212

    15. 33e86k87qn

    16. Trametinib (usan)

    17. N-(3-{3-cyclopropyl-5-[(2-fluoro-4-iodophenyl)amino]-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydropyrido[4,3-d]pyrimidin-1(2h)-yl}phenyl)acetamide

    18. N-[3-[3-cyclopropyl-5-(2-fluoro-4-iodoanilino)-6,8-dimethyl-2,4,7-trioxopyrido[4,3-d]pyrimidin-1-yl]phenyl]acetamide

    19. Acetamide, N-(3-(3-cyclopropyl-5-((2-fluoro-4-iodophenyl)amino)-3,4,6,7-tetrahydro-6,8- Dimethyl-2,4,7-trioxopyrido(4,3-d)pyrimidin-1(2h)-yl)phenyl)-

    20. N-(3-(3-cyclopropyl-5-((2-fluoro-4-iodophenyl)amino)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydropyrido[4,3-d]pyrimidin-1(2h)-yl)phenyl)acetamide

    21. Unii-33e86k87qn

    22. Trametinib [usan:inn]

    23. Trametinibum

    24. Jtp74057

    25. N-(3-(3-cyclopropyl-5-((2-fluoro-4-iodophenyl)amino)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7- Tetrahydropyrido(4,3-d)pyrimidin-1(2h)-yl)phenyl)acetamide

    26. N-(3-(3-cyclopropyl-5-((2-fluoro-4-iodophenyl)amino)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydropyrido(4,3-d)pyrimidin-1(2h)-yl)phenyl)acetamide

    27. N-(3-{3-cyclopropyl-5-((2-fluoro-4-iodophenyl)amino)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7- Tetrahydropyrido(4,3-d)pyrimidin-1(2h)-yl}phenyl)acetamide

    28. Qom

    29. Trametinib [mi]

    30. Trametinib (gsk1120212jtp 74057)

    31. Trametinib [inn]

    32. Trametinib [vandf]

    33. Trametinib [who-dd]

    34. Schembl170938

    35. Gtpl6495

    36. Gsk1120212 (trametinib)

    37. Chembl2103875

    38. Ex-a022

    39. Bcpp000218

    40. Dtxsid901007381

    41. Hms3295i05

    42. Hms3656j11

    43. Bcp02307

    44. Bdbm50531540

    45. Mfcd17215075

    46. Nsc758246

    47. Nsc800956

    48. S2673

    49. Zinc43100709

    50. Akos015850628

    51. Am90271

    52. Ccg-264976

    53. Cs-0060

    54. Db08911

    55. Ex-5957

    56. Nsc-758246

    57. Nsc-800956

    58. Sb16553

    59. Ncgc00263180-01

    60. Ncgc00263180-07

    61. Ncgc00263180-14

    62. Ac-25891

    63. As-19382

    64. Hy-10999

    65. N-[3-[3-cyclopropyl-5-(2-fluoro-4-iodo-anilino)-6,8-dimethyl-2,4,7-trioxo-pyrido[4,3-d]pyrimidin-1-yl]phenyl]acetamide

    66. Ft-0688438

    67. Sw218089-2

    68. A25168

    69. D10175

    70. Gsk1120212 - Jtp-74057

    71. Gsk1120212,jtp-74057, Gsk212

    72. Sr-01000941589

    73. A1-01871

    74. J-523325

    75. Q7833138

    76. Sr-01000941589-1

    77. Brd-k12343256-001-01-4

    78. Acetamide, N-[3-[3-cyclopropyl-5-[(2-fluoro-4-iodophenyl)amino]-3,4,6,7-tetrahydro-6,8-dimethyl-2,4,7-trioxopyrido[4,3-d]pyrimidin-1(2h)-yl]phenyl]-

    79. N-(3-(3-cyclopropyl-5-(2-fluoro-4-iodophenylamino)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydropyrido[4,3-d]pyrimidin-1(2h)-yl)phenyl)acetamide

    80. N-[3-[3-cyclopropyl-5-[(2-fluoro-4-iodophenyl)amino]-3,4,6,7-tetrahydro-6,8-dimethyl-2,4,7-trioxopyrido[4,3-d]pyrimidin-1(2h)-yl]phe Nyl]acetamide

    81. N-[3-[3-cyclopropyl-5-[(2-fluoro-4-iodophenyl)amino]-6,8-dimethyl-2,4,7-trioxopyrido[3,4-e]pyrimidin-1-yl]phenyl]acetamide

    82. N-{3-[3-cyclopropyl-5-(2-fluoro-4-iodoanilino)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydropyrido[4,3-d]pyrimidin-1(2h)-yl]phenyl}ethanimidic Acid

    83. N-{3-[3-cyclopropyl-5-(2-fluoro-4-iodophenylamino)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydro-2h-pyrido[4,3-d]pyrimidin-1-yl]phenyl}acetamide

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 615.4 g/mol
    Molecular Formula C26H23FIN5O4
    XLogP33.4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count5
    Exact Mass615.07788 g/mol
    Monoisotopic Mass615.07788 g/mol
    Topological Polar Surface Area102 Ų
    Heavy Atom Count37
    Formal Charge0
    Complexity1090
    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 Information
    1 of 2  
    Drug NameMekinist
    PubMed HealthTrametinib (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelTrametinib dimethyl sulfoxide is a kinase inhibitor. The chemical name is acetamide, N-[3-[3-cyclopropyl-5-[(2-fluoro-4- iodophenyl)amino]-3,4,6,7-tetrahydro-6,8-dimethyl- 2,4,7-trioxopyrido[4,3-d]pyrimidin-1(2H)-yl]phenyl]-, compound with 1,1-sul...
    Active IngredientTrametinib dimethyl sulfoxide
    Dosage FormTablet
    RouteOral
    Strengtheq 1mg non-solvated parent; eq 0.5mg non-solvated parent; eq 2mg non-solvated parent
    Market StatusPrescription
    CompanyGlaxosmithkline

    2 of 2  
    Drug NameMekinist
    PubMed HealthTrametinib (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelTrametinib dimethyl sulfoxide is a kinase inhibitor. The chemical name is acetamide, N-[3-[3-cyclopropyl-5-[(2-fluoro-4- iodophenyl)amino]-3,4,6,7-tetrahydro-6,8-dimethyl- 2,4,7-trioxopyrido[4,3-d]pyrimidin-1(2H)-yl]phenyl]-, compound with 1,1-sul...
    Active IngredientTrametinib dimethyl sulfoxide
    Dosage FormTablet
    RouteOral
    Strengtheq 1mg non-solvated parent; eq 0.5mg non-solvated parent; eq 2mg non-solvated parent
    Market StatusPrescription
    CompanyGlaxosmithkline

    4.2 Drug Indication

    Trametinib is indicated for the treatment of unresectable or metastatic melanoma with BRAF V600E or V600K mutations, as detected by an FDA-approved test [FDA]. In May 2018, it was approved for use with [DB08912] for the treatment of treat anaplastic thyroid cancer caused by an abnormal BRAF V600E gene.

    FDA Label

    * Melanoma:

    Trametinib as monotherapy or in combination with dabrafenib is indicated for the treatment of adult patients with unresectable or metastatic melanoma with a BRAF V600 mutation (see sections 4. 4 and 5. 1).

    Trametinib monotherapy has not demonstrated clinical activity in patients who have progressed on a prior BRAF inhibitor therapy (see section 5. 1).

    * Adjuvant treatment of melanoma:

    Trametinib in combination with dabrafenib is indicated for the adjuvant treatment of adult patients with Stage III melanoma with a BRAF V600 mutation, following complete resection.

    * Non-small cell lung cancer (NSCLC):

    Trametinib in combination with dabrafenib is indicated for the treatment of adult patients with advanced non-small cell lung cancer with a BRAF V600 mutation.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Trametinib is an anticancer agent which causes apoptosis (or programmed cell death) and inhibits cell proliferation, which are both important in the treatment of malignancies.

    5.2 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    Protein Kinase Inhibitors

    Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    TRAMETINIB
    5.3.2 FDA UNII
    33E86K87QN
    5.3.3 Pharmacological Classes
    Protein Kinase Inhibitors [MoA]; Kinase Inhibitor [EPC]
    5.4 ATC Code

    L01EE01

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01E - Protein kinase inhibitors

    L01EE - Mitogen-activated protein kinase (mek) inhibitors

    L01EE01 - Trametinib

    5.5 Absorption, Distribution and Excretion

    Absorption

    Trametinib is readily absorbed. When an oral administration of trametinib was given to patients with BRAF V600 mutation-positive melanoma, peak plasma concentration occurred 1.5 hours post-dose (Tmax). A single 2 mg oral dose has a bioavailability of 72%. When a dose of 2mg/day is given, the peak plasma concentration (Cmax) is 22.2 ng/mL.

    Route of Elimination

    80% of the dose is excreted in the feces. <20% of the dose is excreted in the urine with <0.1% of the excreted dose in the form of the parent compound.

    Volume of Distribution

    Apparent volume of distribution (Vd/F) = 214 L

    Clearance

    Apparent clearance = 4.9 L/h

    5.6 Metabolism/Metabolites

    Trametinib is metabolized predominantly via deacetylation alone or with mono-oxygenation or in combination with glucuronidation biotransformation pathways in vitro. Deacetylation is likely mediated by hydrolytic enzymes, such as carboxyl-esterases or amidases. The cytochrome P450 enzyme system is not involved with the metabolism of trametinib. The predominant circulating component in the plasma is the parent drug.

    5.7 Biological Half-Life

    Elimination half-life = 3.9-4.8 days.

    5.8 Mechanism of Action

    Trametinib is a reversible, allosteric inhibitor of mitogen-activated extracellular signal regulated kinase 1 _(MEK1)_ and _MEK2_ activation and of_ MEK1_ and _MEK2_ kinase activity. MEK proteins are upstream regulators of the extracellular signal-related kinase (ERK) pathway, which promotes cellular proliferation. Trametinib helps with melanoma with the BRAF V600E or V600K as the mutation results in the constitutive activation of the BRAF pathway which includes MEK1 and MEK2.