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    Amlexanox

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    Xls

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    2D Structure
    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

    2D Structure

    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 Weight 298.29 g/mol
    Molecular Formula C16H14N2O4
    XLogP33.1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count2
    Exact Mass298.09535693 g/mol
    Monoisotopic Mass298.09535693 g/mol
    Topological Polar Surface Area103 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity467
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.