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Chemistry

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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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