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    Enzalutamide

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

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    2D Structure
    Also known as: 915087-33-1, Mdv3100, Mdv-3100, 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-n-methylbenzamide, Mdv 3100, Enzalutamide (mdv3100)
    Molecular Formula
    C21H16F4N4O2S
    Molecular Weight
    464.4  g/mol
    InChI Key
    WXCXUHSOUPDCQV-UHFFFAOYSA-N
    FDA UNII
    93T0T9GKNU
    Enzalutamide is an orally bioavailable, organic, non-steroidal small molecule targeting the androgen receptor (AR) with potential antineoplastic activity. Through a mechanism that is reported to be different from other approved AR antagonists, enzalutamide inhibits the activity of prostate cancer cell ARs, which may result in a reduction in prostate cancer cell proliferation and, correspondingly, a reduction in the serum prostate specific antigen (PSA) level. AR over-expression in prostate cancer represents a key mechanism associated with prostate cancer hormone resistance.
    Enzalutamide is an Androgen Receptor Inhibitor. The mechanism of action of enzalutamide is as an Androgen Receptor Antagonist, and Cytochrome P450 3A4 Inducer, and Cytochrome P450 2C9 Inducer, and Cytochrome P450 2C19 Inducer.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl]-2-fluoro-N-methylbenzamide
    2.1.2 InChI
    InChI=1S/C21H16F4N4O2S/c1-20(2)18(31)28(12-5-4-11(10-26)15(8-12)21(23,24)25)19(32)29(20)13-6-7-14(16(22)9-13)17(30)27-3/h4-9H,1-3H3,(H,27,30)
    2.1.3 InChI Key
    WXCXUHSOUPDCQV-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1(C(=O)N(C(=S)N1C2=CC(=C(C=C2)C(=O)NC)F)C3=CC(=C(C=C3)C#N)C(F)(F)F)C
    2.2 Other Identifiers
    2.2.1 UNII
    93T0T9GKNU
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxo-1-imidazolidinyl)-2-fluoro-n-(methyl-d3)benzamide

    2. 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxo-1-imidazolidinyl)-2-fluoro-n-methyl-benzamide

    3. Enzalutamide D3

    4. Hc 1119

    5. Hc-1119

    6. Mdv 3100

    7. Mdv-3100

    8. Mdv3100

    9. Xtandi

    2.3.2 Depositor-Supplied Synonyms

    1. 915087-33-1

    2. Mdv3100

    3. Mdv-3100

    4. 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-n-methylbenzamide

    5. Mdv 3100

    6. Enzalutamide (mdv3100)

    7. Xtandi

    8. Mdv3100 (enzalutamide)

    9. 93t0t9gknu

    10. Chebi:68534

    11. 4-[3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl]-2-fluoro-n-methylbenzamide

    12. 4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl}-2-fluoro-n-methylbenzamide

    13. 4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl}-2-fluoro-n-methylbenzamide

    14. Benzamide, 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxo-1-imidazolidinyl)-2-fluoro-n-methyl-

    15. Enzalutamide [usan]

    16. Enzalutamide [usan:inn]

    17. Unii-93t0t9gknu

    18. Xtandi (tn)

    19. Enzalutamide [mi]

    20. Enzalutamide; Mdv3100

    21. Enzalutamide (jan/usan)

    22. Enzalutamide [inn]

    23. Enzalutamide [jan]

    24. Mdv3100, Aldrichcpr

    25. Enzalutamide [vandf]

    26. Mls006010067

    27. Enzalutamide [who-dd]

    28. Schembl189749

    29. Gtpl6812

    30. Chembl1082407

    31. Dtxsid10912307

    32. Ex-a046

    33. Bcpp000169

    34. Enzalutamide [orange Book]

    35. Hms3654l07

    36. Hms3672m13

    37. Hms3744c19

    38. Nc-54

    39. Amy10296

    40. Asp-9785

    41. Bcp02361

    42. Bbl102957

    43. Bdbm50425732

    44. Mfcd14155804

    45. Nsc755605

    46. Nsc766085

    47. S1250

    48. Stl556766

    49. Zinc34806477

    50. Akos015851022

    51. Mdv-3100;enzalutamide;mdv 3100

    52. Bcp9000901

    53. Ccg-264879

    54. Cs-0317

    55. Db08899

    56. Nsc-755605

    57. Nsc-766085

    58. Sb20413

    59. Ncgc00263120-01

    60. 4-[3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxo-imidazolidin-1-yl]-2-fluoro-n-methyl-benzamide

    61. Ac-26924

    62. As-17047

    63. Benzamide,4-[3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxo-1-imidazolidinyl]-2-fluoro-n-methyl-

    64. Hy-70002

    65. Mdv3100, 95%

    66. Smr004701227

    67. Ft-0670957

    68. Sw219288-1

    69. A25302

    70. D10218

    71. Ab01565849_02

    72. Sr-01000941580

    73. J-519668

    74. Q1996756

    75. Sr-01000941580-1

    76. Brd-k56851771-001-01-9

    2.4 Create Date
    2007-03-07
    3 Chemical and Physical Properties
    Molecular Weight 464.4 g/mol
    Molecular Formula C21H16F4N4O2S
    XLogP33.6
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count3
    Exact Mass464.09300959 g/mol
    Monoisotopic Mass464.09300959 g/mol
    Topological Polar Surface Area109 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity839
    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 NameXtandi
    PubMed HealthEnzalutamide (By mouth)
    Drug ClassesAntiandrogen, Antineoplastic Agent
    Drug LabelEnzalutamide is an androgen receptor inhibitor. The chemical name is 4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl}-2-fluoro-N-methylbenzamide. The molecular weight is 464.44 and molecular formula is C21...
    Active IngredientEnzalutamide
    Dosage FormCapsule
    RouteOral
    Strength40mg
    Market StatusPrescription
    CompanyAstellas

    2 of 2  
    Drug NameXtandi
    PubMed HealthEnzalutamide (By mouth)
    Drug ClassesAntiandrogen, Antineoplastic Agent
    Drug LabelEnzalutamide is an androgen receptor inhibitor. The chemical name is 4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl}-2-fluoro-N-methylbenzamide. The molecular weight is 464.44 and molecular formula is C21...
    Active IngredientEnzalutamide
    Dosage FormCapsule
    RouteOral
    Strength40mg
    Market StatusPrescription
    CompanyAstellas

    4.2 Drug Indication

    Enzalutamide is indicated for the treatment of patients with metastatic castration-resistant prostate cancer who have previously received docetaxel.

    FDA Label

    Xtandi is indicated for:

    - the treatment of adult men with metastatic hormone-sensitive prostate cancer (mHSPC) in combination with androgen deprivation therapy (see section 5. 1).

    - the treatment of adult men with high-risk non-metastatic castration-resistant prostate cancer (CRPC) (see section 5. 1).

    - the treatment of adult men with metastatic CRPC who are asymptomatic or mildly symptomatic after failure of androgen deprivation therapy in whom chemotherapy is not yet clinically indicated (see section 5. 1).

    - the treatment of adult men with metastatic CRPC whose disease has progressed on or after docetaxel therapy.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Resitance to enzalutamide therapy has been observed. This may occurred due to an upregulation of NF-B2/p52.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    ENZALUTAMIDE
    5.2.2 FDA UNII
    93T0T9GKNU
    5.2.3 Pharmacological Classes
    Androgen Receptor Inhibitor [EPC]; Cytochrome P450 2C19 Inducers [MoA]; Cytochrome P450 2C9 Inducers [MoA]; Cytochrome P450 3A4 Inducers [MoA]; Androgen Receptor Antagonists [MoA]
    5.3 ATC Code

    L02BB04

    L02BB04

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    L - Antineoplastic and immunomodulating agents

    L02 - Endocrine therapy

    L02B - Hormone antagonists and related agents

    L02BB - Anti-androgens

    L02BB04 - Enzalutamide

    5.4 Absorption, Distribution and Excretion

    Absorption

    The pharmacokinetic profile of enzalutamide and N-desmethyl enzalutamide (its major active metabolite) is described by a linear two-compartment model with first-order absorption. Enzalutamide also accumulates. Food does not affect its absorption. Tmax, prostate cancer patients = 1 hour (range of 0.5-3 hours); Cmax, steady state, enzalutamide = 16.6 g/mL; Cmax, steady state, N-desmethyl enzalutamide = 12.7 g/mL; Time to steady state, daily dosing = 28 days;

    Route of Elimination

    Enzalutamide is primarily eliminated by hepatic metabolism. 71% of the dose is recovered in urine (including only trace amounts of enzalutamide and N-desmethyl enzalutamide), and 14% is recovered in feces (0.4% of dose as unchanged enzalutamide and 1% as N-desmethyl enzalutamide).

    Volume of Distribution

    Apparent volume of distribution (Vd/F), single oral dose = 110 L

    Clearance

    Apparent clearance (CL/F), single oral dose = 0.56 L/h (range of 0.33 - 1.02 L/h)

    5.5 Metabolism/Metabolites

    Enzalutamide is hepatically metabolized, primarily by CYP2C8 and CYP3A4. The enzyme that converts enzalutamide to its active metabolite, N-desmethyl enzalutamide, is CYP2C8. The activity of N-desmethyl-enzalutamide is similar to that of the parent compound.

    5.6 Biological Half-Life

    The mean terminal half-life (t1/2) for enzalutamide in patients after a single oral dose is 5.8 days (range 2.8 to 10.2 days). Following a single 160 mg oral dose of enzalutamide in healthy volunteers, the mean terminal t1/2 for N-desmethyl enzalutamide is approximately 7.8 to 8.6 days.

    5.7 Mechanism of Action

    Enzalutamide is a competitive androgen receptor inhibitor that effects multiple stages of the signalling pathway. It is able to inhibit androgen binding to its receptor, androgen receptor nuclear translocation, and subsequent interaction with DNA. As a result, proliferation of prostate cancer cells decreases which ultimately leads to apoptosis and decreased tumour volume.