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Tranilast

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Chemistry

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Also known as: 53902-12-8, Trans-tranilast, Rizaben, 70806-55-2, Tranilastum, Mk 341

Molecular Formula

C₁₈H₁₇NO₅

Molecular Weight

327.3 g/mol

InChI Key

NZHGWWWHIYHZNX-CSKARUKUSA-N

FDA UNII

HVF50SMY6E

Tranilast is an antiallergic drug developed by Kissei Pharmaceuticals. In 1982, it was approved in Japan and South Korea for the management of bronchial asthma. Indications for keloid and hypertrophic scar were added in 1993. It has been used for the treatment of allergic disorders such as asthma, allergic rhinitis and atopic dermatitis.

1 2D Structure

Tranilast

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino]benzoic acid

2.1.2 InChI

InChI=1S/C18H17NO5/c1-23-15-9-7-12(11-16(15)24-2)8-10-17(20)19-14-6-4-3-5-13(14)18(21)22/h3-11H,1-2H3,(H,19,20)(H,21,22)/b10-8+

2.1.3 InChI Key

NZHGWWWHIYHZNX-CSKARUKUSA-N

2.1.4 Canonical SMILES

COC1=C(C=C(C=C1)C=CC(=O)NC2=CC=CC=C2C(=O)O)OC

2.1.5 Isomeric SMILES

COC1=C(C=C(C=C1)/C=C/C(=O)NC2=CC=CC=C2C(=O)O)OC

2.2 Other Identifiers

2.2.1 UNII

HVF50SMY6E

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1 N-(3'-4'-dimethoxycinnamoyl) Anthranilic Acid (n-5'), N(3',4'-dimethoxycinnamoyl) Anthranilic Acid (n-5')

2. 2-((3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl)amino)benzoic Acid

3. Mk-341

4. Mk341

5. N (3', 4'-dimethoxycinnamoyl) Anthranilic Acid (n-5')

6. N-(3',4'-dimethoxycinnamoyl)anthranilic Acid

7. Rizaben

8. Tranilast Hydrate

9. Tranilast Sodium Salt

2.3.2 Depositor-Supplied Synonyms

1. 53902-12-8

2. Trans-tranilast

3. Rizaben

4. 70806-55-2

5. Tranilastum

6. Mk 341

7. N-(3,4-dimethoxycinnamoyl)anthranilic Acid

8. Tranilast Trans-

9. Mk-341

10. Sb-252218

11. (e)-2-(3-(3,4-dimethoxyphenyl)acrylamido)benzoic Acid

12. Tranilast (sb 252218)

13. Hvf50smy6e

14. Nsc-758970

15. 2-((3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl)amino)benzoic Acid

16. Mls000028468

17. Chebi:77572

18. Ncgc00018185-05

19. Smr000058373

20. 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]benzoic Acid

21. 2-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino}benzoic Acid

22. (e)-2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]benzoic Acid

23. Benzoic Acid, 2-((3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl)amino)-

24. Tranilastum [inn-latin]

25. 2-(3-(3,4-dimethoxyphenyl)acrylamido)benzoic Acid

26. Tranilast [usan:inn:jan]

27. 2-[[(e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino]benzoic Acid

28. 2-[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic Acid

29. Tranpro

30. Mfcd00864787

31. 2-({(2e)-3-[3,4-bis(methyloxy)phenyl]prop-2-enoyl}amino)benzoic Acid

32. Rizaben (tn)

33. N-(3',4'-dimethoxycinnamoyl)anthranilic Acid

34. Sr-01000003092

35. N-(3',4'-dimethoxycinnamoyl) Anthranilic Acid

36. Unii-hvf50smy6e

37. Benzoic Acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-

38. Anthranilic Acid, N-(3,4-dimethoxycinnamoyl)-

39. Tranilast- Bio-x

40. Nu-3450

41. Tranilast [inn]

42. Tranilast [jan]

43. Tranilast [mi]

44. Sb 252218

45. Tranilast [usan]

46. Opera_id_1657

47. Dsstox_cid_3693

48. Tranilast [mart.]

49. T 0318

50. Tranilast [who-dd]

51. Dsstox_rid_77152

52. Dsstox_gsid_23693

53. Lopac0_001193

54. Schembl29875

55. Bspbio_003561

56. Zinc797

57. 53902-17-3

58. Mls000759509

59. Mls001065902

60. Mls001077269

61. Mls001424045

62. Mls002207030

63. Mls006010043

64. Spectrum1505333

65. Chembl415324

66. Gtpl6326

67. Tranilast (jp17/usan/inn)

68. Bdbm21613

69. Chebi:92320

70. Hms2051f05

71. Hms2089l07

72. Hms2094i21

73. Hms2230f18

74. Hms3263p07

75. Hms3412g17

76. Hms3648a16

77. Hms3676g17

78. Hms3713j04

79. Pharmakon1600-01505333

80. (2-phenylthiazol-5-yl)methylamine

81. Amy14167

82. Bcp06359

83. Bcp15888

84. Hy-b0195

85. Tox21_110836

86. Tox21_501193

87. Ac-940

88. Ccg-39992

89. Hsci1_000076

90. Nsc758970

91. S5871

92. Akos002841076

93. Tranilast, >=98% (hplc), Powder

94. Db07615

95. Ks-1193

96. Lp01193

97. Nc00171

98. Nsc 758970

99. Sdccgsbi-0051160.p004

100. Ncgc00018185-04

101. Ncgc00018185-06

102. Ncgc00018185-08

103. Ncgc00018185-09

104. Ncgc00018185-10

105. Ncgc00018185-20

106. Ncgc00018185-23

107. Ncgc00018185-26

108. Ncgc00021458-04

109. Ncgc00021458-05

110. Ncgc00021458-07

111. Ncgc00261878-01

112. Ac-35254

113. Bd164491

114. N-5'

115. Sb252218

116. Sbi-0051160.p003

117. Cas-53902-12-8

118. Eu-0101193

119. S1439

120. Sw197551-3

121. N-(3 ,4 -dimethoxycinnamoyl)anthranilic Acid

122. D02027

123. Ab00382987-18

124. Ab00382987-19

125. Ab00382987_21

126. 902t173

127. A829819

128. A923780

129. 2-(3,4-dimethoxy-trans-cinnamoylamino)benzoic Acid

130. Q-201849

131. Q2325594

132. Sr-01000003092-2

133. Sr-01000003092-4

134. Sr-01000003092-9

135. Brd-k17849083-001-02-2

136. Brd-k17849083-001-03-0

137. Brd-k19533706-001-01-9

138. Q27164069

139. Sr-01000003092-16

140. 2-[3-(3,4-dimethoxyphenyl)-acryloylamino]-benzoic Acid

141. 2-[3-(3,4-dimethoxyphenyl)prop-2-enoylamino]benzoic Acid

142. 2-[[3-(3,4-dimethoxyphenyl)-1-oxoprop-2-enyl]amino]benzoic Acid

143. 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propen-1-yl]amino]benzoic Acid

144. Tranilast; 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino] Benzoic Acid

145. D27

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₇NO₅
Molecular Weight	327.3 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	327.11067264 g/mol
Monoisotopic Mass	327.11067264 g/mol
Topological Polar Surface Area	84.9 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	464
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

For the treatment of bronchial asthma, keloid and hypertrophic scar, and allergic disorders such as asthma, allergic rhinitis and atopic dermatitis.

5 Pharmacology and Biochemistry

5.1 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.)

Histamine H1 Antagonists

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)

Calcium Channel Blockers

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)

Platelet Aggregation Inhibitors

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)

Anti-Allergic Agents

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)

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