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    Also known as: Arn-509, 956104-40-8, Erleada, Jnj-56021927, Arn 509, Apalutamide [inn]
    Molecular Formula
    C21H15F4N5O2S
    Molecular Weight
    477.4  g/mol
    InChI Key
    HJBWBFZLDZWPHF-UHFFFAOYSA-N
    FDA UNII
    4T36H88UA7
    Apalutamide
    Apalutamide is a small molecule and androgen receptor (AR) antagonist with potential antineoplastic activity. Apalutamide binds to AR in target tissues thereby preventing androgen-induced receptor activation and facilitating the formation of inactive complexes that cannot be translocated to the nucleus. This prevents binding to and transcription of AR-responsive genes. This ultimately inhibits the expression of genes that regulate prostate cancer cell proliferation and may lead to an inhibition of cell growth in AR-expressing tumor cells.
    1 2D Structure

    Apalutamide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[7-[6-cyano-5-(trifluoromethyl)pyridin-3-yl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide
    2.1.2 InChI
    InChI=1S/C21H15F4N5O2S/c1-27-17(31)13-4-3-11(8-15(13)22)30-19(33)29(18(32)20(30)5-2-6-20)12-7-14(21(23,24)25)16(9-26)28-10-12/h3-4,7-8,10H,2,5-6H2,1H3,(H,27,31)
    2.1.3 InChI Key
    HJBWBFZLDZWPHF-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CNC(=O)C1=C(C=C(C=C1)N2C(=S)N(C(=O)C23CCC3)C4=CC(=C(N=C4)C#N)C(F)(F)F)F
    2.2 Other Identifiers
    2.2.1 UNII
    4T36H88UA7
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Arn-509

    2. Erleada

    2.3.2 Depositor-Supplied Synonyms

    1. Arn-509

    2. 956104-40-8

    3. Erleada

    4. Jnj-56021927

    5. Arn 509

    6. Apalutamide [inn]

    7. Arn509

    8. Apalutamide (arn-509)

    9. 4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)-2-fluoro-n-methylbenzamide

    10. 4t36h88ua7

    11. 956104-40-8 (free Base)

    12. 4-[7-[6-cyano-5-(trifluoromethyl)pyridin-3-yl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-n-methylbenzamide

    13. 4-{7-[6-cyano-5-(trifluoromethyl)pyridin-3-yl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl}-2-fluoro-n-methylbenzamide

    14. 4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro(3.4)octan-5-yl)-2-fluoro-n-methylbenzamide

    15. Unii-4t36h88ua7

    16. Ar509

    17. Apalutamidearn509

    18. Erleada (tn)

    19. Jnj 56021927

    20. Apalutamide (jan/inn)

    21. Apalutamide [mi]

    22. Apalutamide [jan]

    23. Apalutamide [who-dd]

    24. Mls006011109

    25. Schembl909297

    26. Gtpl9043

    27. Chembl3183409

    28. Apalutamide [orange Book]

    29. Dtxsid40241899

    30. Ex-a089

    31. Hms3656n12

    32. Amy24182

    33. Bcp05829

    34. Ar509/ar-509

    35. Bdbm50094975

    36. Mfcd22380626

    37. Nsc771649

    38. Nsc794776

    39. S2840

    40. Zinc43174901

    41. Akos025401932

    42. Ccg-264760

    43. Cs-0885

    44. Db11901

    45. Nsc-771649

    46. Nsc-794776

    47. Pb27306

    48. Ncgc00346725-01

    49. Ncgc00346725-02

    50. Ncgc00346725-06

    51. Ac-27403

    52. As-35181

    53. Hy-16060

    54. Smr004702891

    55. Sw220300-1

    56. 24872560, Erleada, C21h15f4n5o2s

    57. D11040

    58. J-519596

    59. Q21098975

    60. Benzamide, 4-(7-(6-cyano-5-(trifluoromethyl)-3-pyridinyl)-8-oxo-6-thioxo-5,7-diazaspiro(3.4)oct-5-yl)-2-fluoro-n-methyl-

    2.4 Create Date
    2008-08-18
    3 Chemical and Physical Properties
    Molecular Weight 477.4 g/mol
    Molecular Formula C21H15F4N5O2S
    XLogP33
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count3
    Exact Mass477.08825856 g/mol
    Monoisotopic Mass477.08825856 g/mol
    Topological Polar Surface Area121 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity886
    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

    Indicated for the treatment of patients with non-metastatic, castration-resistant prostate cancer (NM-CRPC).

    FDA Label

    Erleada is indicated:

    in adult men for the treatment of non metastatic castration resistant prostate cancer (nmCRPC) who are at high risk of developing metastatic disease. in adult men for the treatment of metastatic hormone-sensitive prostate cancer (mHSPC) in combination with androgen deprivation therapy (ADT).

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    In an open-label, uncontrolled, multi-center, single-arm dedicated QT study in 45 patients with CRPC, an exposure-QT analysis suggested a concentration-dependent increase in QTcF for apalutamide and its active metabolite. Apalutamide demonstrated an antitumor activity in the mouse xenograft models of prostate cancer, where it decreased tumor cell proliferation and reduced tumor volume.

    5.2 ATC Code

    L02BB05

    L - Antineoplastic and immunomodulating agents

    L02 - Endocrine therapy

    L02B - Hormone antagonists and related agents

    L02BB - Anti-androgens

    L02BB05 - Apalutamide

    5.3 Absorption, Distribution and Excretion

    Absorption

    Mean absolute oral bioavailability was approximately 100%. Median time to achieve peak plasma concentration (tmax) was 2 hours (range: 1 to 5 hours). Median tmax may be increased with a high-fat meal. Administration of oral apalutamide at recommended dosages resulted in a steady state within 4 weeks with a maximum peak concentration (Cmax) and AUC of 6.0 mcg/mL and 100 mcgh/mL, respectively. Cmax and AUC of apalutamide is expected to increase in a dose-proportional manner. The mean mean peak-to-trough ratio was 1.63 indicating low daily fluctuations in the plasma concentrations of the drug. The major active metabolite N-desmethyl apalutamide Cmax was 5.9 mcg/mL (1.0) and AUC was 124 mcgh/mL (23) at steady-state after the recommended dosage.

    Route of Elimination

    Apalutamide and its main active metabolite are subject to both renal and focal elimination. Up to 70 days following a single oral administration of radiolabeled apalutamide, 65% of the dose was recovered in urine (1.2% of dose as unchanged apalutamide and 2.7% as N-desmethyl apalutamide) and 24% was recovered in feces (1.5% of dose as unchanged apalutamide and 2% as N-desmethyl apalutamide).

    Volume of Distribution

    The mean apparent volume of distribution at steady-state of apalutamide was approximately 276 L.

    Clearance

    The CL/F of apalutamide was 1.3 L/h after single dosing and increased to 2.0 L/h at steady-state after once-daily dosing. An increase in apparent clearance (CL/F) was observed with repeat dosing, likely due to induction of apalutamides own metabolism. The auto-induction effect likely reached its maximum at the recommended dosage because exposure of apalutamide across the dose range of 30 to 480 mg is dose-proportional.

    5.4 Metabolism/Metabolites

    Apalutamide primarily undergoes CYP2C8 and CYP3A4-mediated metabolism to its pharmacologically active metabolite, N-desmethyl apalutamide. The contribution of CYP2C8 and CYP3A4 in the total metabolism of apalutamide is approximately 58% and and 13% following single dose but changes to 40% and 37%, respectively at steady-state. The auto-induction of CYP3A4-mediated metabolism by apalutamide may explain the increase in CYP3A4 enzymatic activity at steady-state. Based on systemic exposure, relative potency, and pharmacokinetic properties, N-desmethyl apalutamide likely contributed to the clinical activity of apalutamide.

    5.5 Biological Half-Life

    The mean effective half-life for apalutamide in patients with NM-CRPC was approximately 3 days at steady-state.

    5.6 Mechanism of Action

    Persistent androgen receptor (AR) signaling is a common feature of castration-resistant prostate cancer (CRPC), attributed to AR gene-amplification, AR gene mutation, increased AR expression or increased androgen biosynthesis in prostate tumors. Apalutamide is an antagonist of AR that to the binding-site in the ligand-binding domain of the receptor with the IC50 of 16 nM. Upon binding, apalutamide disrupts AR signalling, inhibits DNA binding, and impedes AR-mediated gene transcription. Apalutamide impairs the translocation of AR from the cytoplasm to the nucleus thus reduces the concentrations of AR available to interact with the androgen response-elements (AREs). Upon treatment with apalutamide, AR was not recruited to the DNA promoter-regions. Its main metabolite, N-desmethyl apalutamide, is a less potent inhibitor of AR, and exhibited one-third the activity of apalutamide in an in vitro transcriptional reporter assay.

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    09-Jan-2021
    31-Aug-2024
    KGS
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