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Amlexanox

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Chemistry

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Also known as: 68302-57-8, Amoxanox, Aphthasol, 2-amino-7-isopropyl-5-oxo-5h-chromeno[2,3-b]pyridine-3-carboxylic acid, Amlenanox, Elics

Molecular Formula

C₁₆H₁₄N₂O₄

Molecular Weight

298.29 g/mol

InChI Key

SGRYPYWGNKJSDL-UHFFFAOYSA-N

FDA UNII

BRL1C2459K

Amlexanox is an anti-aphthous ulcer drug. Amlexanox inhibits the synthesis and release of inflammatory mediators, including leukotrienes and histamine, from mast cells, neutrophils, and mononuclear cells. Amlexanox also acts as a leukotriene D4 antagonist and a phosphodiesterase inhibitor. Amlexanox decreases the time ulcers take to heal as well as the pain associated with the ulcers.

The physiologic effect of amlexanox is by means of Decreased Histamine Release.

1 2D Structure

Amlexanox

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-5-oxo-7-propan-2-ylchromeno[2,3-b]pyridine-3-carboxylic acid

2.1.2 InChI

InChI=1S/C16H14N2O4/c1-7(2)8-3-4-12-9(5-8)13(19)10-6-11(16(20)21)14(17)18-15(10)22-12/h3-7H,1-2H3,(H2,17,18)(H,20,21)

2.1.3 InChI Key

SGRYPYWGNKJSDL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)C1=CC2=C(C=C1)OC3=NC(=C(C=C3C2=O)C(=O)O)N

2.2 Other Identifiers

2.2.1 UNII

BRL1C2459K

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-amino-7-isopropyl-5-oxo-5h-(1)benzopyrano(2,3b)pyridine-3-carboxylic Acid

2. Aa 673

3. Aa-673

4. Amoxanox

5. Aphthasol

6. Chx 3673

2.3.2 Depositor-Supplied Synonyms

1. 68302-57-8

2. Amoxanox

3. Aphthasol

4. 2-amino-7-isopropyl-5-oxo-5h-chromeno[2,3-b]pyridine-3-carboxylic Acid

5. Amlenanox

6. Elics

7. Amlexanoxum [latin]

8. Aa-673

9. Amlexanoxo [spanish]

10. Amlexanoxo

11. Amlexanoxum

12. Chx 3673

13. Aphtheal

14. Chx-3673

15. 2-amino-5-oxo-7-propan-2-ylchromeno[2,3-b]pyridine-3-carboxylic Acid

16. 2-amino-5-oxo-7-(propan-2-yl)-5h-chromeno[2,3-b]pyridine-3-carboxylic Acid

17. 2-amino-7-isopropyl-5-oxo-5h-(1)benzopyrano(2,3-b)pyridine-3-carboxylic Acid

18. Aa673;amoxanox;chx3673

19. Brl1c2459k

20. Chebi:31205

21. 2-amino-7-(1-methylethyl)-5-oxo-5h-chromeno[2,3-b]pyridine-3-carboxylic Acid

22. Ncgc00167472-01

23. Amlexanox [usan:inn:jan]

24. Dsstox_cid_2595

25. 2-amino-7-isopropyl-5-oxo-5h-chromeno-[2,3-b]pyridine-3-carboxylic Acid

26. Aa 673

27. 5h-(1)benzopyrano(2,3-b)pyridine-3-carboxylic Acid, 2-amino-7-(1-methylethyl)-5-oxo-

28. Dsstox_rid_76651

29. Dsstox_gsid_22595

30. Aptheal

31. Apthera

32. Orarinse

33. Oradisc A

34. Aphthasol (tn)

35. Anw

36. Smr000466352

37. Cas-68302-57-8

38. Ccris 2686

39. Solfa (tn)

40. Brn 0556384

41. Unii-brl1c2459k

42. 4wbo

43. 5h-[1]benzopyrano[2,3-b]pyridine-3-carboxylic Acid, 2-amino-7-(1-methylethyl)-5-oxo-

44. Amlexanox [usan:inn:ban:jan]

45. Amlexanox- Bio-x

46. Mfcd00864790

47. 2-amino-7-(1-methylethyl)-5-oxo-5h-[1]benzopyrano[2,3-b]pyridine-3-carboxylic Acid

48. Aa-673(amlexanox)

49. Amlexanox [inn]

50. Amlexanox [jan]

51. Amlexanox [mi]

52. Amlexanox [usan]

53. Amlexanox [vandf]

54. Amlexanox [mart.]

55. Amlexanox [who-dd]

56. Chembl1096

57. Schembl29642

58. Zinc928

59. Mls000759466

60. Mls001424059

61. Mls006010129

62. Bidd:gt0709

63. Us10214536, Amlexanox

64. Gtpl7113

65. Amlexanox (jp17/usan/inn)

66. Amlexanox [orange Book]

67. Amlexanox, >=98% (hplc)

68. Dtxsid2022595

69. Chx3673

70. Aa673

71. Bdbm357857

72. Hms2051f13

73. Hms2235m08

74. Hms3393f13

75. Hms3715b14

76. Bcp28222

77. Hy-b0713

78. Tox21_112476

79. 2-amino-7-isopropyl-5-oxochromeno[2,3-b]pyridine-3-carboxylic Acid

80. S3648

81. 2-amino-7-isopropyl-5-oxo-5h-chromeno[2,3-b]pyridine-3-carboxylicacid

82. Akos015900498

83. Tox21_112476_1

84. Ac-1192

85. Ccg-100953

86. Db01025

87. Ds-1396

88. Nc00203

89. Ncgc00167472-02

90. Ncgc00167472-03

91. Ncgc00167472-14

92. Ba164161

93. Ft-0641176

94. D01828

95. Ab00639947-06

96. Ab00639947_08

97. 302a578

98. A836094

99. L001037

100. Q695611

101. Amlexanox, United States Pharmacopeia (usp) Reference Standard

102. 2-amino-7-isopropyl-5-oxo-5h-[1]benzopyrano[2,3-b] Pyridine-3-carboxylic Acid

103. 2-amino-7-isopropyl-5-oxo-chromeno[2,3-b]pyridine-3-carboxylic Acid;amlexanox

104. 2-amino-7-(1-methylethyl)-5-oxo-5h-[1]benzopyrano[2,3-b]pyridine-3-carboxylic Acid Amoxanox Aa-673 Chx-3673 Aphthasol Elics Solfa

105. 5h-(1)benzopyrano(2,3-.beta.)pyridine-3-carboxylic Acid, 2-amino-7-(1-methylethyl)-5-oxo-

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₄N₂O₄
Molecular Weight	298.29 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	298.09535693 g/mol
Monoisotopic Mass	298.09535693 g/mol
Topological Polar Surface Area	103 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	467
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

Used as a paste in the mouth to treat aphthous ulcers (canker sores).

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Amlexanox is a mucoadhesive oral paste which has been clinically proven to abort the onset, accelerate healing and resolve the pain of aphthous ulcers (canker sores). It decreases the time ulcers take to heal. Because amlexanox decreases the healing time, it also decreases the pain you feel. Recent studies have also shown that the majority of ulcers can be prevented by application of the paste during the prodromal (pre-ulcerative) phase of the disease. Recurrent Aphthous Ulcers (RAU) also known as Recurrent Aphthous Stomatitis (RAS) is recognized as the most common oral mucosal disease known to man. Estimates suggest that 20% - 25% of the general population suffer at least one incidence of aphthous ulcers each year. Amlexanox is also being investigated for its anti-allergenic and anti-inflammatory properties.

5.2 MeSH Pharmacological Classification

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.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

AMLEXANOX

5.3.2 FDA UNII

BRL1C2459K

5.3.3 Pharmacological Classes

Physiologic Effects [PE] - Decreased Histamine Release

5.4 ATC Code

A - Alimentary tract and metabolism

A01 - Stomatological preparations

A01A - Stomatological preparations

A01AD - Other agents for local oral treatment

A01AD07 - Amlexanox

R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03D - Other systemic drugs for obstructive airway diseases

R03DX - Other systemic drugs for obstructive airway diseases

R03DX01 - Amlexanox

5.5 Absorption, Distribution and Excretion

Absorption

No significant absorption directly through the active ulcer. Most of the systemic absorption is via the gastrointestinal tract.

5.6 Metabolism/Metabolites

Metabolized to hydroxylated and conjugated metabolites.

5.7 Biological Half-Life

Elimination half-life is 3.5 ± 1.1 hours.

5.8 Mechanism of Action

As a benzopyrano-bipyridine carboxylic acid derivative, amlexanox has anti-inflammatory and antiallergic properties. It inhibits chemical mediatory release of the slow-reacting substance of anaphylaxis (SRS-A) and may have antagonistic effects on interleukin-3. When cells are under stress, they release an inactive form of human fibroblast growth factor 1 (FGF-1), a potent mitogen (entity that causes mitosis). Amlexanox binds to FGF1, increasing its conformational stability, sterically blocking Cu(2+) induced oxidation which normally leads to activation of FGF-1.

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