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Prestwick2_001003

Prestwick2_001003

Synopsis, Chemistry

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Also known as: Apazone, Cinnopropazone, Prolixan, Azapropazonum, Azapropazona, 13539-59-8

Molecular Formula

C₁₆H₂₀N₄O₂

Molecular Weight

300.36 g/mol

InChI Key

MPHPHYZQRGLTBO-UHFFFAOYSA-N

FDA UNII

K2VOT966ZI

An anti-inflammatory agent used in the treatment of rheumatoid arthritis. It also has uricosuric properties and has been used to treat gout.

1 2D Structure

Prestwick2_001003

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-(dimethylamino)-9-methyl-2-propylpyrazolo[1,2-a][1,2,4]benzotriazine-1,3-dione

2.1.2 InChI

InChI=1S/C16H20N4O2/c1-5-6-11-14(21)19-13-9-10(2)7-8-12(13)17-16(18(3)4)20(19)15(11)22/h7-9,11H,5-6H2,1-4H3

2.1.3 InChI Key

MPHPHYZQRGLTBO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCC1C(=O)N2C3=C(C=CC(=C3)C)N=C(N2C1=O)N(C)C

2.2 Other Identifiers

2.2.1 UNII

K2VOT966ZI

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-(dimethylamino)-9-methyl-2-propyl-1h-pyrazolo(1,2-a)(1,2,4)benzotriazine-1,3(2h)-dione

2. Apazone

3. Apazone Dihydrate

4. Dihydrate, Apazone

5. Prolixan

6. Rheumox

7. Tolyprin

2.3.2 Depositor-Supplied Synonyms

1. Apazone

2. Cinnopropazone

3. Prolixan

4. Azapropazonum

5. Azapropazona

6. 13539-59-8

7. Cinnamin

8. Rheumox

9. Azapropazon

10. Mitrolan

11. Sinnamin

12. Prolix

13. Xani

14. Azapropazone (anhydrous)

15. Ahr-3018

16. Apazone [usan]

17. Prolixan 300

18. Nsc-102824

19. Mi 85

20. Ahr 3018

21. Mi-85

22. Azapropazone Dihydrate

23. Azapropazon [german]

24. Nsc 102824

25. Azapropazone [inn]

26. 5-(dimethylamino)-9-methyl-2-propyl-1h-pyrazolo(1,2-a)(1,2,4)benzotriazine-1,3(2h)-dione

27. 3-dimethylamino-7-methyl-1,2-(n-propylmalonyl)-1,2-dihydro-1,2,4-benzotriazine

28. K2vot966zi

29. 1,2-dihydro-3-dimethylamino-7-methyl-1,2-(propylmalonyl)-1,2,4-benzotriazine

30. 1h-pyrazolo(1,2-a)(1,2,4)benzotriazine-1,3(2h)-dione, 5-(dimethylamino)-9-methyl-2-propyl-

31. 5-(dimethylamino)-9-methyl-2-propyl-1h-pyrazolo[1,2-a][1,2,4]benzotriazine-1,3(2h)-dione

32. Mls002703748

33. Chebi:38010

34. Apazone (usan)

35. Azapropazone (inn)

36. Nsc102824

37. Azapropazon (german)

38. 1h-pyrazolo[1,2-a][1,2,4]benzotriazine-1,3(2h)-dione, 5-(dimethylamino)-9-methyl-2-propyl-

39. 5-(dimethylamino)-9-methyl-2-propylpyrazolo[1,2-a][1,2,4]benzotriazine-1,3-dione

40. Ahr-3018;nsc-102824;nsc102824;

41. Mi-85di

42. Azapropazonum [inn-latin]

43. Azapropazona [inn-spanish]

44. 5-(dimethylamino)-9-methyl-2-propyl-1h-benzo[e]pyrazolo[1,2-a][1,2,4]triazine-1,3(2h)-dione

45. Smr001233401

46. Einecs 236-913-8

47. Unii-k2vot966zi

48. Brn 0623763

49. Ncgc00016701-01

50. Prolixan (tn)

51. Cas-13539-59-8

52. Tolyprin (salt/mix)

53. Apazone [mi]

54. Prestwick0_001003

55. Prestwick1_001003

56. Prestwick2_001003

57. Prestwick3_001003

58. Schembl3190

59. Dsstox_cid_23735

60. Dsstox_rid_80859

61. Nciopen2_007171

62. Dsstox_gsid_45408

63. Azapropazone [mart.]

64. Bspbio_001125

65. Mls002154093

66. (+/-)-apazone

67. Apazone Dihydrate (salt/mix)

68. Azapropazone [who-dd]

69. Spbio_003006

70. Bpbio1_001239

71. Apazone, (+/-)-

72. Chembl1565476

73. Dtxsid6045408

74. Hms1571i07

75. Hms2098i07

76. Hms2231l14

77. Hms3372m10

78. Hms3715i07

79. Tox21_110569

80. Akos015914210

81. Ccg-221003

82. Ncgc00179297-01

83. Ncgc00179297-04

84. 1,2-(propylmalonyl)-1,2,4-benzotriazine

85. Hy-116442

86. Ab00513995

87. Cs-0065495

88. D02966

89. Q368222

90. Sr-01000838825

91. Sr-01000838825-2

92. Wln: T B566 Bnv Evn Hn Dhj D3 Gn1&1 L1

93. 3-dimethylamino-7-methyl-1,2-dihydro-1,2,4-benzotriazine

94. 3-dimethylamino-7-methyl-1-2-(n-propylmalonyl)-1,2,4-benzotriazine

95. 1,2-dihydro-3-(dimethylamino)-7-methyl-1,2-(propylmalonyl)-1,2,4-benzotriazine

96. 1h-pyrazolo[1,2,4]benzotriazine-1,3(2h)-dione, 5-(dimethylamine)-9-methyl-2-propyl-

97. 1h-pyrazolo[1,2,4]benzotriazine-1,3(2h)-dione, 5-(dimethylamino)-9-methyl-2-propyl-

98. 5-(dimethylamino)-9-methyl-2-propyl-1h-pyrazolo[1,2,4]benzotriazine-1,3(2h)-dione

99. 5-(dimethylamino)-9-methyl-2-propyl-1h-pyrazolo[1,2,4]benzotriazine-1,3(2h)dione

100. 5-(dimethylamino)-9-methyl-2-propyl-pyrazolo[1,2-a][1,2,4]benzotriazine-1,3-dione

101. 1h-pyrazolo(1,2-a)(1,2,4)benzotriazine-1,3(2h)-dione, 5-(dimethylamine)-9-methyl-2-propyl-

102. 5-dimethylamino-9-methyl-2-propylpyrazolo(1,2-a)(1,2,4)benzotriazine-1,3(2h)-dione

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₀N₄O₂
Molecular Weight	300.36 g/mol
XLogP3	4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	300.15862589 g/mol
Monoisotopic Mass	300.15862589 g/mol
Topological Polar Surface Area	56.2 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	516
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Uricosuric Agents

Gout suppressants that act directly on the renal tubule to increase the excretion of uric acid, thus reducing its concentrations in plasma. (See all compounds classified as Uricosuric Agents.)

4.2 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AX - Other antiinflammatory and antirheumatic agents, non-steroids

M01AX04 - Azapropazone