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Istradefylline

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Synopsis

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Health Canada Patents

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Chemistry

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Also known as: 155270-99-8, Kw-6002, Kw 6002, Istradefylline (kw-6002), Nouriast, Nourianz

Molecular Formula

C₂₀H₂₄N₄O₄

Molecular Weight

384.4 g/mol

InChI Key

IQVRBWUUXZMOPW-PKNBQFBNSA-N

FDA UNII

2GZ0LIK7T4

Istradefylline, or KW6002, was developed by Kyowa Hakko Kirin in Japan for the treatment of Parkinson's disease as an adjunct to standard therapy. Unlike standard dopaminergic therapies for Parkinson's, Istradefylline targets adenosine A2A receptors in the basal ganglia. This region of the brain is highly involved in motor control. Istradefylline is indicated as an adjunct treatment to [levodopa] and [carbidopa] for Parkinson's disease. This drug was first approved in Japan on 25 March 2013. Istradefylline was granted FDA approval on 27 August 2019.

1 2D Structure

Istradefylline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

8-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-7-methylpurine-2,6-dione

2.1.2 InChI

InChI=1S/C20H24N4O4/c1-6-23-18-17(19(25)24(7-2)20(23)26)22(3)16(21-18)11-9-13-8-10-14(27-4)15(12-13)28-5/h8-12H,6-7H2,1-5H3/b11-9+

2.1.3 InChI Key

IQVRBWUUXZMOPW-PKNBQFBNSA-N

2.1.4 Canonical SMILES

CCN1C2=C(C(=O)N(C1=O)CC)N(C(=N2)C=CC3=CC(=C(C=C3)OC)OC)C

2.1.5 Isomeric SMILES

CCN1C2=C(C(=O)N(C1=O)CC)N(C(=N2)/C=C/C3=CC(=C(C=C3)OC)OC)C

2.2 Other Identifiers

2.2.1 UNII

2GZ0LIK7T4

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 8-(2-(3,4-dimethoxyphenyl)ethenyl)-1,3-diethyl-3,7-dihydro-7-methyl-1h-purine-2,6-dione

2. Kw 6002

3. Kw-6002

4. Kw6002

2.3.2 Depositor-Supplied Synonyms

1. 155270-99-8

2. Kw-6002

3. Kw 6002

4. Istradefylline (kw-6002)

5. Nouriast

6. Nourianz

7. 8-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-7-methyl-purine-2,6 -dione

8. (e)-8-(3,4-dimethoxystyryl)-1,3-diethyl-7-methyl-1h-purine-2,6(3h,7h)-dione

9. 8-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-7-methylpurine-2,6-dione

10. (e)-8-(3,4-dimethoxystyryl)-1,3-diethyl-7-methylxanthine

11. 2gz0lik7t4

12. Chembl431770

13. (e)-8-(3,4-dimethoxystyryl)-1,3-diethyl-7-methyl-3,7-dihydro-1h-purine-2,6-dione

14. 8-((1e)-2-(3,4-dimethoxyphenyl)ethenyl)-1,3-diethyl-7-methyl-3,7-dihydro-1h-purine-2,6-dione

15. 8-[(e)-2-(3,4-dimethoxyphenyl)vinyl]-1,3-diethyl-7-methyl-3,7-dihydro-1h-purine-2,6-dione

16. Kw6002

17. Unii-2gz0lik7t4

18. Istradefyline

19. Istradefylline (jan/usan/inn)

20. Istradefylline [usan:inn:jan]

21. Ncgc00253737-01

22. Nourianz (tn)

23. Nouriast (tn)

24. Istradefylline [usan]

25. Istradefylline [mi]

26. Dsstox_cid_31441

27. Dsstox_rid_97327

28. Istradefylline [inn]

29. Istradefylline [jan]

30. Dsstox_gsid_57652

31. Mls006010633

32. Schembl633262

33. Schembl633263

34. Gtpl5608

35. Istradefylline [who-dd]

36. Dtxsid7057652

37. Chebi:134726

38. Hms3884p16

39. Istradefylline, >=98% (hplc)

40. Bcp02194

41. Zinc3803921

42. Istradefylline [orange Book]

43. Tox21_113855

44. Bdbm50176050

45. Mfcd00928421

46. S2790

47. Akos015966268

48. Am84508

49. Bcp9000824

50. Ccg-268457

51. Cs-0737

52. Db11757

53. 1h-purine-2,6-dione, 3,7-dihydro-1,3-diethyl-8-(2-(3,4-dimethoxyphenyl)ethenyl)-7-methyl-, (e)-

54. Ac-30957

55. Hy-10888

56. Ls-14789

57. Smr004701638

58. Cas-155270-99-8

59. I1100

60. Sw220139-1

61. D04641

62. Kw 6002;kw-6002;kw6002

63. 270i998

64. L001483

65. Q905783

66. Sr-01000945278

67. J-009183

68. J-519355

69. Sr-01000945278-1

70. Brd-k40096621-001-01-2

71. 1,3-diethyl-7-methyl-8-(3,4-dimethoxystyryl)xanthine

72. (e)- 8-(3,4-dimethoxystyryl)-1,3-diethyl-7-methylxanthine

73. 8-(3,4-dimethoxystyryl)-1,3-diethyl-7-methyl-1h-purine-2,6(3h,7h)-dione

74. 8-[2-(3,4-dimethoxy-phenyl)-vinyl]-1,3-diethyl-7-methyl-3,7-dihydro-purine-2,6-dione

75. 8-[2-(3,4-dimethoxy-phenyl)-vinyl]-1,3-diethyl-7-methyl-3,9-dihydro-purine-2,6-dione

76. (e)-8-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-3,7-dihydro-7-methyl-1h-purine-2,6-dione

77. 8-[(1e)-2-(2-(3,4-dimethoxyphenyl)ethenyl]-1,3-diethyl-3,7-dihydro-7-methyl-1h-purine-2,6-dione

78. 8-[(e)-2-(3,4-dimethoxy-phenyl)-vinyl]-1,3-diethyl-7-methyl-3,7-dihydro-purine-2,6-dione

2.4 Create Date

2005-12-16

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₄N₄O₄
Molecular Weight	384.4 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	384.17975526 g/mol
Monoisotopic Mass	384.17975526 g/mol
Topological Polar Surface Area	76.9 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	613
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Istradefylline is indicated in adjunct to levodopa and carbidopa in the treatment of Parkinson's disease.

Treatment of Parkinson's disease

Istradefylline is indicated in adults as an adjunctive treatment to levodopa based regimens in patients with Parkinson's disease (PD) experiencing OFF time.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Istradefylline is a selective adenosine A_2A receptor inhibitor. It has a long duration of action as it is given once daily and has a half life of 64-69 hours. Patients taking this medication should be monitored for dyskinesia, hallucinations, and lack of impulse control. Consider dose reductions for these patients.

5.2 MeSH Pharmacological Classification

Adenosine A2 Receptor Antagonists

Compounds that selectively bind to and block the activation of ADENOSINE A2 RECEPTORS. (See all compounds classified as Adenosine A2 Receptor Antagonists.)

5.3 ATC Code

N04

N - Nervous system

N04 - Anti-parkinson drugs

N04C - Other antiparkinson drugs

N04CX - Other antiparkinson drugs

N04CX01 - Istradefylline

5.4 Absorption, Distribution and Excretion

Absorption

Istradefylline reaches a C_max of 181.1ng/mL with a T_max of 2.0h and an AUC of 11,100ng\*h/mL. M1, the primary active metabolite, reaches a C_max of 4.34ng/mL with a T_max of 3.5h. The M8 metabolite reaches a C_max of 12.6ng/mL with a T_max of 3.0h and an AUC of 610ng\*h/mL.

Route of Elimination

A 3mg/kg oral dose given to male rats was 17.6% elminated in the urine and 68.3% eliminated in the feces. In urine, 5.31% of the total dose was the M3 metabolite and 1.96% of the total dose was the M1 metabolite. In feces, 30.60% of the total dose was the M3 metabolite, 9.34% of the total dose was the M1 metabolite, 8.33% of the total dose was the M10 metabolite, and 1.62% of the total dose was unchanged istradefylline.

Volume of Distribution

The apparent volume of distribution of istradefylline is 448-557L.

Clearance

The apparent clearance of istradefylline is 4.1-6.0L/h.

5.5 Metabolism/Metabolites

The primary metabolite found in urine is the active 4'-O-monodesmethyl istradefylline (M1). Istradefylline is metabolized mainly by CYP1A1, CYP3A4, and CYP3A5. CYP1A2, CYP2B6, CYP2C8, CYP2C9, CYP2C18, and CYP2D6 also partly contribute the the metabolism of istradefylline. Other identified metabolites are 1--hydroxylated-4-O-demethyl istradefylline (M2), 3,4-O-didemethyl istradefylline (M3), M1 sulfate conjugate (M4), M1 glucuronide (M5), 1--hydroxylated istradefylline (M8) and hydrogenated M3 (M10).

5.6 Biological Half-Life

The terminal elimination half life of istradefylline was 64-69 hours.

5.7 Mechanism of Action

Istradefylline is a selective adenosine A_2A receptor inhibitor. These receptors are found in the basal ganglia, a region of the brain that suffers degeneration in Parkinson's disease, and is also significantly involved in motor control. A_2A receptors are also expressed on GABAergic medium spiny neurons within the indirect striato-pallidal pathway. The GABAergic action of this pathway is thereby reduced. Istradefylline has 56 times the affinity for A_2A receptors than A₁ receptors.