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    Chemistry

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    Also known as: 1197953-54-0, Alunbrig, Ap-26113, Brigatinib [usan], Brigatinib (ap-26113), Hyw8db273j
    Molecular Formula
    C29H39ClN7O2P
    Molecular Weight
    584.1  g/mol
    InChI Key
    AILRADAXUVEEIR-UHFFFAOYSA-N
    FDA UNII
    HYW8DB273J
    Brigatinib
    Brigatinib is an orally available inhibitor of receptor tyrosine kinases anaplastic lymphoma kinase (ALK) and the epidermal growth factor receptor (EGFR) with potential antineoplastic activity. Brigatinib binds to and inhibits ALK kinase and ALK fusion proteins as well as EGFR and mutant forms. This leads to the inhibition of ALK kinase and EGFR kinase, disrupts their signaling pathways and eventually inhibits tumor cell growth in susceptible tumor cells. In addition, AP26113 appears to overcome mutation-based resistance. ALK belongs to the insulin receptor superfamily and plays an important role in nervous system development; ALK dysregulation and gene rearrangements are associated with a series of tumors. EGFR is overexpressed in a variety of cancer cell types.
    Brigatinib is a Kinase Inhibitor. The mechanism of action of brigatinib is as a Tyrosine Kinase Inhibitor, and Cytochrome P450 3A Inducer.
    1 2D Structure

    Brigatinib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]pyrimidine-2,4-diamine
    2.1.2 InChI
    InChI=1S/C29H39ClN7O2P/c1-35-15-17-37(18-16-35)21-11-13-36(14-12-21)22-9-10-24(26(19-22)39-2)33-29-31-20-23(30)28(34-29)32-25-7-5-6-8-27(25)40(3,4)38/h5-10,19-21H,11-18H2,1-4H3,(H2,31,32,33,34)
    2.1.3 InChI Key
    AILRADAXUVEEIR-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1CCN(CC1)C2CCN(CC2)C3=CC(=C(C=C3)NC4=NC=C(C(=N4)NC5=CC=CC=C5P(=O)(C)C)Cl)OC
    2.2 Other Identifiers
    2.2.1 UNII
    HYW8DB273J
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Alunbrig

    2. Ap26113

    2.3.2 Depositor-Supplied Synonyms

    1. 1197953-54-0

    2. Alunbrig

    3. Ap-26113

    4. Brigatinib [usan]

    5. Brigatinib (ap-26113)

    6. Hyw8db273j

    7. Ap 26113

    8. (2-((5-chloro-2-((2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)phenyl)dimethylphosphine Oxide

    9. 5-chloro-4-n-(2-dimethylphosphorylphenyl)-2-n-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]pyrimidine-2,4-diamine

    10. 2,4-pyrimidinediamine, 5-chloro-n4-(2-(dimethylphosphinyl)phenyl)-n2-(2-methoxy-4-(4-(4-methyl-1-piperazinyl)-1-piperidinyl)phenyl)-

    11. 5-chloro-n4-(2-(dimethylphosphoryl)phenyl)-n2-(2-methoxy-4-(4-(4-methylpiperazin-1- Yl)piperidin-1-yl)phenyl)pyrimidine-2,4-diamine

    12. 2,4-pyrimidinediamine, 5-chloro-n4-[2-(dimethylphosphinyl)phenyl]-n2-[2-methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-

    13. 5-chloro-n~4~-[2-(dimethylphosphoryl)phenyl]-n~2~-{2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidine-2,4-diamine

    14. Unii-hyw8db273j

    15. Brigatiib

    16. Alunbrig (tn)

    17. 5-chloro-n4-(2-(dimethylphosphoryl)phenyl)-n2-(2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)pyrimidine-2,4-diamine

    18. 5-chloro-n4-[2-(dimethylphosphoryl)phenyl]-n2-{2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidine-2,4-diamine

    19. 6gy

    20. Brigatinib [mi]

    21. Brigatinib [inn]

    22. Brigatinib [jan]

    23. Brigatinib (jan/usan)

    24. Brigatinib [usan:inn]

    25. Brigatinib; Ap26113

    26. Brigatinib (ap26113)

    27. Brigatinib [who-dd]

    28. 5-chloro-n4-[2-(dimethylphosphinyl)phenyl]-n2-[2-methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-2,4-pyrimidinediamine

    29. Gtpl7741

    30. Brigatinib [orange Book]

    31. Chembl3545311

    32. Schembl11916361

    33. Ex-a775

    34. Dtxsid501027929

    35. Amy10294

    36. Bcp17214

    37. Bdbm50185140

    38. Mfcd29472221

    39. Nsc784728

    40. Nsc787457

    41. Akos030257612

    42. Zinc148723177

    43. Cs-4278

    44. Db12267

    45. Nsc-784728

    46. Nsc-787457

    47. Sb40412

    48. Compound 11q [pmid: 27144831]

    49. Ncgc00483924-01

    50. (2-((5-chloro-2-((2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)phenyl)dimethyl-,delta5-phosphanone

    51. Ac-29958

    52. As-75176

    53. Hy-12857

    54. Db-118419

    55. Ft-0700112

    56. S8229

    57. J3.535.964h

    58. D10866

    59. Q27456393

    60. (2-((5-chloro-2-((2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)phenyl)dimethyl-,.delta.5-phosphanone

    2.4 Create Date
    2012-11-30
    3 Chemical and Physical Properties
    Molecular Weight 584.1 g/mol
    Molecular Formula C29H39ClN7O2P
    XLogP34.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count8
    Exact Mass583.2591382 g/mol
    Monoisotopic Mass583.2591382 g/mol
    Topological Polar Surface Area85.9 Ų
    Heavy Atom Count40
    Formal Charge0
    Complexity835
    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 1  
    Drug NameALUNBRIG
    Active IngredientBRIGATINIB
    CompanyARIAD (Application Number: N208772. Patents: 9012462, 9273077, 9611283)

    4.2 Drug Indication

    The anaplastic lymphoma kinase positive, metastatic non-small cell lung cancer (ALK+ NSCLC), represents only 3-5% of the NSCLC cancer cases, but the ALK mutation, overexpression and presence in several oncogenic fusion proteins in solid and hematologic tumors have pointed out the importance as well as its potential as a cancer therapy target. The ALK-related cases of NSCLC are associated with the presence of the fusion gene EML4-ALK which fused the ALK protein with the echinoderm microtubule-associated protein like-4 whose original function is the correct formation of microtubules. The presence of the aberrant fusion protein results in abnormal signaling that provokes increased cell growth, proliferation and survival. Crizotinib is indicated for the treatment of such cases but the presence of ALK kinase domain mutations confer resistance to the treatment. Thus, brigatinib is indicated for the treatment of patients with ALK+ NSCLC with intolerance to Crizotinib.

    FDA Label

    Alunbrig is indicated as monotherapy for the treatment of adult patients with anaplastic lymphoma kinase (ALK)positive advanced nonsmall cell lung cancer (NSCLC) previously not treated with an ALK inhibitor.

    Alunbrig is indicated as monotherapy for the treatment of adult patients with anaplastic lymphoma kinase ALKpositive advanced NSCLC previously treated with crizotinib.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Brigitanib inhibits proliferation and in vitro viability of cells expressing the fusion protein EML4-ALK as well as 17 crizotinib-resistant ALK mutants. Its action is expanded to cells expressing EGFR deletions, ROS1-L2026M, FLT3-F691L and FLT3-D835Y. Brigitanib presents a dose-dependent inhibition of tumor growth, tumor burden and prolonged survival in mice EML4-ALK xenograft models. Time course of Brigatinib and exposure-response studies are still unknown.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    BRIGATINIB
    5.2.2 FDA UNII
    HYW8DB273J
    5.2.3 Pharmacological Classes
    Kinase Inhibitor [EPC]; Tyrosine Kinase Inhibitors [MoA]; Cytochrome P450 3A Inducers [MoA]
    5.3 ATC Code

    L01XE43

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01E - Protein kinase inhibitors

    L01ED - Anaplastic lymphoma kinase (alk) inhibitors

    L01ED04 - Brigatinib

    5.4 Absorption, Distribution and Excretion

    Absorption

    Administration of brigatinib at a concentration of 90 mg generates a Cmax of 552 ng/ml and AUC of 8165 ng h/ml while the administration of 180 mg presents a Cmax of 1452 ng/ml and AUC of 20276 ng h/ml. It has a dose proportional exposure with an accumulation ratio on the range of 1.9 to 2.4. Following oral administration of brigatinib, the Tmax is presented in a range from 1 to 4 hours. Consumption of a high-fat meal compared to overnight fasting reduces Cmax by 13% without presenting an effect on AUC.

    Route of Elimination

    The elimination of brigatinib is divided in 65% in feces and 25% in urine. From the elimination in both compartments, the unchanged for of brigatinib represented 41% of the total in feces and 86% in urine.

    Volume of Distribution

    The apparent volume of distribution at steady state is 153 L.

    Clearance

    After oral administration of180 mg of brigatinib, the apparent oral clearance at steady-state is 12.7 L/h.

    5.5 Metabolism/Metabolites

    Brigatinib is metabolized by CYP2C8 (72.4%) and CYP3A4 (27.6%) in human liver microsomes and hepatocytes. The two major metabolites generated are the N-demethylated form and the cysteine conjugated form. Oral administration of radiolabelled brigatinib showed the systemic presence of 91.5% in the unchanged form and 3.5% of the primary metabolite AP26123. The AUC of AP26123 is less than 10% of the AUC of brigatinib and presented an inhibitory effect 3 fold lower.

    5.6 Biological Half-Life

    The half-life of brigatinib at steady-state was 25 hours.

    5.7 Mechanism of Action

    Brigitanib acts as a tyrosine kinase inhibitor with activity against multiple kinases including ALK, ROS1, insulin-like growth factor 1 receptor and against EGFR deletions and point mutations. It acts by inhibiting ALK phosphorylation and the activation of downstream signaling proteins.

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    Brigatinib

    Registrant Name : Takeda Pharmaceutical Company Korea Ltd.

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    DOSAGE - TABLET;ORAL - 180MG

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