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Propentofylline

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Synopsis

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Chemistry

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Also known as: 55242-55-2, Propentophylline, Hextol, Hwa 285, Karsivan, Hwa-285

Molecular Formula

C₁₅H₂₂N₄O₃

Molecular Weight

306.36 g/mol

InChI Key

RBQOQRRFDPXAGN-UHFFFAOYSA-N

FDA UNII

5RTA398U4H

1 2D Structure

Propentofylline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-methyl-1-(5-oxohexyl)-7-propylpurine-2,6-dione

2.1.2 InChI

InChI=1S/C15H22N4O3/c1-4-8-18-10-16-13-12(18)14(21)19(15(22)17(13)3)9-6-5-7-11(2)20/h10H,4-9H2,1-3H3

2.1.3 InChI Key

RBQOQRRFDPXAGN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCN1C=NC2=C1C(=O)N(C(=O)N2C)CCCCC(=O)C

2.2 Other Identifiers

2.2.1 UNII

5RTA398U4H

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(5'-oxohexyl)-3-methyl-7-propylxanthine

2. Hwa 285

3. Hwa-285

2.3.2 Depositor-Supplied Synonyms

1. 55242-55-2

2. Propentophylline

3. Hextol

4. Hwa 285

5. Karsivan

6. Hwa-285

7. 3-methyl-1-(5-oxohexyl)-7-propylxanthine

8. 3-methyl-1-(5-oxohexyl)-7-propylpurine-2,6-dione

9. 3-methyl-1-(5-oxohexyl)-7-propyl-1h-purine-2,6(3h,7h)-dione

10. 3,7-dihydro-3-methyl-1-(5-oxohexyl)-7-propyl-1h-purine-2,6-dione

11. 1h-purine-2,6-dione, 3,7-dihydro-3-methyl-1-(5-oxohexyl)-7-propyl-

12. Nsc-752424

13. 5rta398u4h

14. 3-methyl-1-(5-oxohexyl)-7-propyl-3,7-dihydro-1h-purine-2,6-dione

15. Ncgc00015861-04

16. Albert-285

17. Dsstox_cid_25189

18. Dsstox_rid_80736

19. Dsstox_gsid_45189

20. Propentofylina

21. Propentofyllinum

22. Hoe-285

23. Propentofylina [inn-spanish]

24. Propentofyllinum [inn-latin]

25. Cas-55242-55-2

26. Sr-01000075642

27. Brn 1156290

28. Unii-5rta398u4h

29. Viviq

30. Propentofylline [inn:ban:jan]

31. 3arx

32. Poy

33. Propentofylline, Solid

34. 3as2

35. Spectrum3_001834

36. Lopac-p-9689

37. Propentofylline (jan/inn)

38. Propentofylline [mi]

39. Lopac0_001015

40. Schembl74602

41. Bspbio_003507

42. Propentofylline [inn]

43. Propentofylline [jan]

44. 5-26-14-00082 (beilstein Handbook Reference)

45. Mls001060796

46. Hwa285

47. Propentofylline [mart.]

48. Chembl1079905

49. Dtxsid4045189

50. Propentofylline [who-dd]

51. Chebi:32061

52. Kbio3_003012

53. Hms2197a12

54. Hms3263k11

55. Hms3355f02

56. Zinc1915505

57. Tox21 110247

58. Tox21_110247

59. Tox21_501015

60. Bdbm50492435

61. Nsc752424

62. Akos016003243

63. Tox21_110247_1

64. Ccg-205095

65. Db06479

66. Lp01015

67. Nsc 752424

68. Sdccgsbi-0050988.p003

69. Ncgc00015861-01

70. Ncgc00015861-02

71. Ncgc00015861-03

72. Ncgc00015861-06

73. Ncgc00015861-07

74. Ncgc00015861-08

75. Ncgc00015861-09

76. Ncgc00094307-01

77. Ncgc00094307-02

78. Ncgc00094307-03

79. Ncgc00178023-01

80. Ncgc00261700-01

81. Smr000486263

82. Sbi-0050988.p002

83. 1-(5-oxohexyl)-3-methyl-7-propylxanthine

84. Db-052700

85. Hy-107203

86. Cs-0027629

87. Eu-0101015

88. Ft-0630675

89. D01630

90. P 9689

91. 242p552

92. Q2888695

93. Sr-01000075642-1

94. Sr-01000075642-5

95. Brd-k59273480-001-01-5

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₂N₄O₃
Molecular Weight	306.36 g/mol
XLogP3	0.7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	7
Exact Mass	306.16919058 g/mol
Monoisotopic Mass	306.16919058 g/mol
Topological Polar Surface Area	75.5 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	454
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 Indication

Investigated for use/treatment in alzheimer's disease.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Neuroprotective Agents

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)

5.2 ATC Code

N - Nervous system

N06 - Psychoanaleptics

N06B - Psychostimulants, agents used for adhd and nootropics

N06BC - Xanthine derivatives

N06BC02 - Propentofylline

5.3 Mechanism of Action

Propentofylline is a xanthine derivative and phosphodiesterase inhibitor with purported neuroprotective effects. It inhibits both phosphodiesterase and adenosine uptake. Phosphodiesterase has shown to associated with age-related memory impairment and Alzheimer's disease. -Amyloid protein 142 (42) can induce apoptosis in the cultured hippocampal neurons, suggesting that it plays an important role in causing neurodegeneration in Alzheimer's disease. Propentofylline is also capable of activating a cAMPPKA system, depressing the caspase cascade and modifying Bcl-2 family proteins. Propentofylline blocked both the apoptotic features induced by 42 and further induced an anti-apoptotic protein, Bcl-2. It suggests that the protection of propentofylline on the 42-induced neurotoxicity is caused by enhancing anti-apoptotic action through cAMPPKA system.

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