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1 US Medicaid Prescriptions, 3 Finished Drug Prices, 16 Annual Reports

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16 Annual Reports

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Polpharma Enzalutamide

Synopsis

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Chemistry

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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

Enzalutamide

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 Formula	C₂₁H₁₆F₄N₄O₂S
Molecular Weight	464.4 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	3
Exact Mass	464.09300959 g/mol
Monoisotopic Mass	464.09300959 g/mol
Topological Polar Surface Area	109 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	839
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Xtandi
PubMed Health	Enzalutamide (By mouth)
Drug Classes	Antiandrogen, Antineoplastic Agent
Drug Label	Enzalutamide 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 Ingredient	Enzalutamide
Dosage Form	Capsule
Route	Oral
Strength	40mg
Market Status	Prescription
Company	Astellas

2 of 2
Drug Name	Xtandi
PubMed Health	Enzalutamide (By mouth)
Drug Classes	Antiandrogen, Antineoplastic Agent
Drug Label	Enzalutamide 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 Ingredient	Enzalutamide
Dosage Form	Capsule
Route	Oral
Strength	40mg
Market Status	Prescription
Company	Astellas

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

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.

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