Amlexanox

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Amlexanox
Amlexanox.svg
Systematic (IUPAC) name
2-amino-7-isopropyl-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylic acid
Clinical data
Trade names Aphthasol
AHFS/Drugs.com monograph
MedlinePlus a601017
Routes of
administration		 Topical
Pharmacokinetic data
Biological half-life 3.5 hours
Excretion Renal (17%)
Identifiers
CAS Number 68302-57-8 YesY
ATC code A01AD07 (WHO) R03DX01
PubChem CID: 2161
IUPHAR/BPS 7113
DrugBank DB01025 YesY
ChemSpider 2076 YesY
UNII BRL1C2459K YesY
KEGG D01828 YesY
ChEBI CHEBI:31205 YesY
ChEMBL CHEMBL1096 YesY
Chemical data
Formula C16H14N2O4
Molecular mass 298.293 g/mol
  • O=C1c3cc(ccc3Oc2nc(c(cc12)C(=O)O)N)C(C)C
  • 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) YesY
  • Key:SGRYPYWGNKJSDL-UHFFFAOYSA-N YesY
  (verify)

Amlexanox (trade name Aphthasol) is an anti-inflammatory antiallergic immunomodulator used to treat recurrent aphthous ulcers (canker sores), and (in Japan) several inflammatory conditions. This drug has been discontinued in the U.S.[1]

Medical uses

Amlexanox is the active ingredient in a common topical treatment for recurrent aphthous ulcers of the mouth (canker sores),[2] reducing both healing time[3] and pain.[4] Amlexanox 5% paste is well-tolerated,[5] and is typically applied four times per day directly on the ulcers.[3] A 2011 review found it to be the most effective treatment of the eight treatments investigated for recurrent canker sores.[6] It is also used to treat ulcers associated with Behçet disease.[7]

In Japan, it is used to treat bronchial asthma, allergic rhinitis and conjunctivitis.[8]

Contraindications

The drug is contraindicated in those with known allergies to it.[3]

Adverse effects

Amlexanox may cause a slightly painful stinging or burning sensation, nausea or diarrhea.[3]


Mechanism of action

The drug is an anti-inflammatory,[8] antiallergic[9] immunomodulator.[10]

Its mechanism of action is not well-determined, but it might inhibit inflammation by inhibiting the release of histamine and leukotrienes.[8] It has been shown to selectively inhibt TBK1[disambiguation needed] and IKK-ε, producing reversible weight loss and improved insulin sensitivity, reduced inflammation and attenuated hepatic steatosis without affecting food intake in obese mice.[11]

Physical and chemical properties

The chemical itself is an odorless, white to yellowish-white powder.[8]

The 5% preparation for patient use is an adherent beige paste,[3][8] and it is also available in some countries as a tablet that adheres to the ulcer in the mouth.[4]

Pharmacokinetics

Amlexanox applied to an aphthous ulcer is largely absorbed through the gastrointestinal tract; an insignificant amount enters the bloodstream through the ulcer itself. After a single 100 mg dose, mean maximum serum concentration occurs 2.4 +/- 0.9 hours after application, with a half-life of elimination (through urine) of 3.5 +/- 1.1 hours. With multiple daily applications (four doses per day), steady state serum levels occur after one week, with no accumulation occurring after four weeks.[8]

History

The patent for its use as a treatment for aphthous ulcers was issued in November 1994 to inventors Kakubhai R. Vora, Atul Khandwala and Charles G. Smith, and assigned to Chemex Pharmaceuticals, Inc.[12]

Society and culture

Legal status

A prescription is required to obtain the medication.[13]


Economics

A 2011 review found a one-week supply of amlexanox 5% paste to cost $30.[6]

Research

A review found that, as of July 2011, robust studies investigating its effectiveness alongside other canker sore treatments were still needed.[14]

Because it is an inhibitor of the protein kinases TBK1 and IKK-ε,[11] which are implicated in the etiology of type II diabetes and obesity,[15] amlexanox may be a candidate for human clinical trials testing in relation to these diseases.[11]

Synthesis

Amlexanox synthesis:[16]

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  3. ↑ 3.0 3.1 3.2 3.3 3.4 Lua error in package.lua at line 80: module 'strict' not found.
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  6. ↑ 6.0 6.1 Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ 8.0 8.1 8.2 8.3 8.4 8.5 Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ 11.0 11.1 11.2 Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ US patent 5362737, Kakubhai R. Vora, Atul Khandwala, Charles G. Smith, "Methods of treating aphthous ulcers and other mucocutaneous disorders with amlexanox", assigned to Chemex Pharmaceuticals, Inc. 
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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