Amlexanox

Source: Wikipedia, the free encyclopedia.
Amlexanox
Clinical data
Trade namesAphthasol
AHFS/Drugs.comMonograph
MedlinePlusa601017
Routes of
administration		Topical
ATC code
Pharmacokinetic data
Elimination half-life3.5 hours
ExcretionRenal (17%)
Identifiers
  • 2-amino-7-isopropyl-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylic acid
JSmol)
  • 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) checkY
  • Key:SGRYPYWGNKJSDL-UHFFFAOYSA-N checkY
  (verify)

Amlexanox (trade name Aphthasol) is an

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

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

Its mechanism of action is not well-determined, but it might inhibit inflammation by inhibiting the release of

nonalcoholic fatty liver disease[10]

Chemistry

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

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.[11]

Society and culture

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.[12]

Because it is an

type II diabetes and obesity,[13] amlexanox may be a candidate for human clinical trials testing in relation to these diseases.[9]

Synthesis

Amlexanox synthesis:[14]

References

  1. ^ "Amlexanox (Aphthasol®)". Archived from the original on 20 November 2013. Retrieved 20 November 2013.
  2. PMID 17323710
    .
  3. ^ a b c d e "Amlexanox". MedlinePlus. U.S. National Library of Medicine. February 2009. Retrieved 12 February 2013.
  4. ^ a b Plewa MC (March 2012). "Pediatric Aphthous Ulcers Treatment & Management". Medscape Reference. Medscape. Retrieved 14 February 2013.
  5. ^ "Amlexanox". PubChem. U.S. National Library of Medicine. Retrieved 12 February 2013.
  6. ^
    PMID 21977491
    .
  7. ^ Yousefi M, Ferringer T, Lee S, Bang D (July 2012). "Dermatologic Aspects of Behcet Disease Treatment & Management". Medscape Reference. Medscape. Retrieved 14 February 2013.
  8. ^
    S2CID 24492356
    .
  9. ^
    PMID 23396211
    .
  10. PMID 28683283
    .
  11. ^ US patent 5362737, Vora KR, Khandwala A, Smith CG, "Methods of treating aphthous ulcers and other mucocutaneous disorders with amlexanox", published 1994-11-08, assigned to Chemex Pharmaceuticals, Inc. 
  12. PMID 22258979
    .
  13. PMID 19737522
    .
  14. PMID 3989816
    .
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