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{{Drugbox
{{Drugbox
| IUPAC_name       = 2-amino-7-(1-methylethyl)-5-oxo-5''H''-chromeno[2,3-''b'']<br>pyridine-3-carboxylic acid
| Watchedfields = changed
| image             = Amlexanox.svg
| verifiedrevid = 456689729
| CAS_number        = 68302-57-8
| IUPAC_name = 2-amino-7-isopropyl-5-oxo-5''H''-chromeno[2,3-''b'']pyridine-3-carboxylic acid
| ATC_prefix        = A01
| image = Amlexanox Wiki Str.png
| ATC_suffix        = AD07
 
| PubChem          = 2161
 
| DrugBank          = APRD00795
<!--Clinical data-->
| C=16|H=14|N=2|O=4
| tradename = Aphthasol
| molecular_weight = 298.293 g/mol
| Drugs.com = {{drugs.com|monograph|amlexanox}}
| smiles            = CC(C)C1=CC2=C(C=C1)OC3=NC(=C(C=C3C2=O)C(=O)O)N
| MedlinePlus = a601017
| bioavailability   =  
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| protein_bound     =  
| pregnancy_US = <!-- A / B            / C / D / X -->
| metabolism       =  
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC                  / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| routes_of_administration = Topical
 
<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life = 3.5 hours
| elimination_half-life = 3.5 hours
| excretion         = [[Kidney|Renal]] (17%)
| excretion = [[Kidney|Renal]] (17%)
| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
 
| pregnancy_US      = <!-- A / B            / C / D / X -->
<!--Identifiers-->
| pregnancy_category=
| CASNo_Ref = {{cascite|correct|CAS}}
| legal_AU          = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| CAS_number_Ref = {{cascite|correct|??}}
| legal_CA          =  <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
| CAS_number = 68302-57-8
| legal_UK          = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| ATC_prefix = A01
| legal_US          =  <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| ATC_suffix = AD07
| legal_status      =  
| ATC_supplemental = {{ATC|R03|DX01}}
| routes_of_administration = Topical
| PubChem = 2161
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01025
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2076
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BRL1C2459K
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D01828
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 31205
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1096
 
<!--Chemical data-->
| C=16 | H=14 | N=2 | O=4
| molecular_weight = 298.293 g/mol
| smiles = O=C1c3cc(ccc3Oc2nc(c(cc12)C(=O)O)N)C(C)C
| InChI = 1/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)
| InChIKey = SGRYPYWGNKJSDL-UHFFFAOYAX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SGRYPYWGNKJSDL-UHFFFAOYSA-N
}}
}}
'''Amlexanox''' is a medication with [[antiallergic]] and [[anti-inflammatory]] effects used in the treatment of [[aphthous ulcer]]s (canker sores).
__NOTOC__
{{SI}}
{{CMG}}
== Overview ==
'''Amlexanox''' (trade name '''Aphthasol''') is an [[anti-inflammatory]] [[antiallergic]] [[immunomodulator]] used to treat recurrent [[aphthous ulcer]]s (canker sores), and (in Japan) several [[inflammation|inflammatory conditions]]. This drug has been discontinued in the U.S.<ref>{{cite web|title=Amlexanox (Aphthasol®) |url=http://www.childrensdmc.org/HealthLibrary/default.aspx?sid=1&pTitle=&ContentTypeID=26&ContentID=665&pTitle=Drug&alpha=A&AdditionalTitle=Aphthasol%C2%AE|accessdate=20 November 2013}}</ref>


{{pharma-stub}}
==Medical uses==
Amlexanox is the active ingredient in a common topical treatment for recurrent [[aphthous ulcers]] of the mouth (canker sores),<ref name=gonsalves_2007/> reducing both healing time<ref name=medline_2009/> and pain.<ref name=medscape_aphthous_2012/>  Amlexanox 5% paste is well-tolerated,<ref name=pubchem/> and is typically applied four times per day directly on the ulcers.<ref name=medline_2009/>  A 2011 review found it to be the most effective treatment of the eight treatments investigated for recurrent canker sores.<ref name=bailey_2011/>  It is also used to treat ulcers associated with [[Behçet disease]].<ref name=medscape_behcet_2012/>
 
In Japan, it is used to treat [[bronchial asthma]], allergic [[rhinitis]] and [[conjunctivitis]].<ref name=bell_2005/>
 
==Contraindications==
The drug is contraindicated in those with known allergies to it.<ref name=medline_2009/>
 
==Adverse effects==
Amlexanox may cause a slightly painful stinging or burning sensation, nausea or diarrhea.<ref name=medline_2009/>
 
<!--==Overdose==-->
<!--==Interactions==-->
==Mechanism of action==
The drug is an [[anti-inflammatory]],<ref name=bell_2005/> [[antiallergic]]<ref name=mesh_2009/> [[immunomodulator]].<ref name=elad_2011/> 
 
Its mechanism of action is not well-determined, but it might inhibit inflammation by inhibiting the release of [[histamine]] and [[leukotrienes]].<ref name=bell_2005/> It has been shown to selectively inhibt [[TBK1]] and [[IKBKE|IKK-ε]], producing reversible weight loss and improved insulin sensitivity, reduced inflammation and attenuated hepatic steatosis without affecting food intake in obese mice.<ref name=reilly_2013/>
 
==Physical and chemical properties==
The chemical itself is an odorless, white to yellowish-white powder.<ref name=bell_2005/>
 
The 5% preparation for patient use is an adherent beige paste,<ref name=medline_2009/><ref name=bell_2005/> and it is also available in some countries as a tablet that adheres to the ulcer in the mouth.<ref name=medscape_aphthous_2012/>
 
==Pharmacokinetics==
Amlexanox applied to an aphthous ulcer is largely absorbed through the [[gastrointestinal tract]]; an insignificant amount enters the [[bloodstream]] through the ulcer itself.<!-- ref name=bell_2005 /-->  After a single 100 mg dose, mean maximum [[serum (blood)|serum]] concentration occurs 2.4 +/- 0.9 hours after application, with a half-life of elimination (through urine) of 3.5 +/- 1.1 hours.<!-- ref name=bell_2005 /-->  With multiple daily applications (four doses per day), steady state serum levels occur after one week, with no accumulation occurring after four weeks.<ref name=bell_2005/>
 
==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.<ref name=patent/>
 
==Society and culture==
===Legal status===
A [[prescription drug|prescription]] is required to obtain the medication.<ref name=burgess_2008/>
 
<!--===Recreational use===-->
===Economics===
A 2011 review found a one week supply of amlexanox 5% paste to cost $30.<ref name=bailey_2011/>
 
==Research==
A review found that, {{asof|2011|7|lc=y}}, robust studies investigating its effectiveness alongside other canker sore treatments were still needed.<ref name=kuteyi_2012/>
 
Because it is an [[enzyme inhibitor|inhibitor]] of the [[protein kinase]]s [[TBK1]] and [[IκB kinase|IKK-ε]],<ref name=reilly_2013/> which are implicated in the [[etiology]] of [[type II diabetes]] and [[obesity]],<ref name=Chiang/> amlexanox may be a candidate for human clinical trials testing in relation to these diseases.<ref name=reilly_2013/>
 
<!--==Veterinary use==-->
==Synthesis==
[[File:Amlexanoxsynthesis.png|thumb|center|600px|Amlexanox synthesis:<ref>{{Cite doi|10.1021/jm50001a005}}</ref>]]
{{Stomatological preparations}}
{{Stomatological preparations}}
{{Drugs for obstructive airway diseases}}
==References==
{{reflist|35em|refs=
<ref name=bailey_2011>{{cite journal | author = Bailey J, McCarthy C, Smith RF | title = Clinical inquiry. What is the most effective way to treat recurrent canker sores? | journal = J Fam Pract | volume = 60 | issue = 10 | pages = 621–32 | date = October 2011 | pmid = 21977491 | doi = | url = http://www.jfponline.com/Pages.asp?AID=9930 }}</ref>
<ref name=bell_2005>{{cite journal | author = Bell J | title = Amlexanox for the treatment of recurrent aphthous ulcers | journal = Clin Drug Investig | volume = 25 | issue = 9 | pages = 555–66 | year = 2005 | pmid = 17532700 | doi = 10.2165/00044011-200525090-00001| url = http://www.medscape.com/viewarticle/512792 }}</ref>
<ref name=burgess_2008>{{cite journal | author = Burgess JA, van der Ven PF, Martin M, Sherman J, Haley J | title = Review of over-the-counter treatments for aphthous ulceration and results from use of a dissolving oral patch containing glycyrrhiza complex herbal extract | journal = J Contemp Dent Pract | volume = 9 | issue = 3 | pages = 88–98 | year = 2008 | pmid = 18335124 | doi = | url = }}</ref>
<ref name=elad_2011>{{cite journal | author = Elad S, Epstein JB, von Bültzingslöwen I, Drucker S, Tzach R, Yarom N | title = Topical immunomodulators for management of oral mucosal conditions, a systematic review; Part II: miscellaneous agents | journal = Expert Opin Emerg Drugs | volume = 16 | issue = 1 | pages = 183–202 | date = March 2011 | pmid = 21244328 | doi = 10.1517/14728214.2011.528390 }}</ref>
<ref name=gonsalves_2007>{{cite journal | author = Gonsalves WC, Chi AC, Neville BW | title = Common oral lesions: Part I. Superficial mucosal lesions | journal = Am Fam Physician | volume = 75 | issue = 4 | pages = 501–7 | date = February 2007 | pmid = 17323710 | doi = | url = http://www.aafp.org/afp/2007/0215/p501.html }}</ref>
<ref name=kuteyi_2012>{{cite journal | author = Kuteyi T, Okwundu CI | title = Topical treatments for HIV-related oral ulcers | journal = Cochrane Database Syst Rev | volume = 1 | issue = | pages = CD007975 | year = 2012 | pmid = 22258979 | doi = 10.1002/14651858.CD007975.pub2 | editor1-last = Kuteyi | editor1-first = Teslim }}</ref>
<ref name=medline_2009>{{cite web |url=http://www.nlm.nih.gov/medlineplus/druginfo/meds/a601017.html |title=Amlexanox |date=February 2009 |work=MedlinePlus |publisher=U.S. National Library of Medicine |accessdate=12 February 2013}}</ref>
<ref name=medscape_behcet_2012>{{cite web |author = Yousefi M, Ferringer T, Lee S, Bang D | title=Dermatologic Aspects of Behcet Disease Treatment & Management |date=July 2012 |work=Medscape Reference|publisher=Medscape |accessdate=14 February 2013 |url=http://emedicine.medscape.com/article/1122381-treatment}}</ref>
<ref name=medscape_aphthous_2012>{{cite web | author = Plewa MC | title=Pediatric Aphthous Ulcers Treatment & Management |date=March 2012 |work=Medscape Reference|publisher=Medscape |accessdate=14 February 2013 |url=http://emedicine.medscape.com/article/909213-treatment}}</ref>
<ref name=mesh_2009>{{cite web |url=http://www.nlm.nih.gov/cgi/mesh/2009/MB_cgi?mode=&term=amlexanox |title=Amlexanox |date=2009 |work=MeSH |publisher=U.S. National Library of Medicine |accessdate=12 February 2013}}</ref>
<ref name=patent>{{cite patent |country=US |number=5362737 |status=patent |title=Methods of treating aphthous ulcers and other mucocutaneous disorders with amlexanox |pubdate= |date= November 8, 1994 |inventor=Kakubhai R. Vora, Atul Khandwala, Charles G. Smith |assign1=Chemex Pharmaceuticals, Inc.}}</ref>
<ref name=pubchem>{{cite web |url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?q=all&cid=2161#ec |title=Amlexanox |work=PubChem |publisher=U.S. National Library of Medicine |accessdate=12 February 2013}}</ref>
<ref name=reilly_2013>{{cite journal | author = Reilly SM, Chiang SH, Decker SJ, Chang L, Uhm M, Larsen MJ, Rubin JR, Mowers J, White NM, Hochberg I, Downes M, Yu RT, Liddle C, Evans RM, Oh D, Li P, Olefsky JM, Saltiel AR | title = An inhibitor of the protein kinases TBK1 and IKK-ɛ improves obesity-related metabolic dysfunctions in mice | journal = Nat. Med. | volume = 19| issue = 3| pages = 313–21| date = February 2013 | pmid = 23396211 | doi = 10.1038/nm.3082 }}</ref>
<ref name=Chiang>{{cite journal | author = Chiang SH, Bazuine M, Lumeng CN, Geletka LM, Mowers J, White NM, Ma JT, Zhou J, Qi N, Westcott D, Delproposto JB, Blackwell TS, Yull FE, Saltiel AR | title = The protein kinase IKKepsilon regulates energy balance in obese mice | journal = Cell | volume = 138 | issue = 5 | pages = 961–75 | date = September 2009 | pmid = 19737522 | pmc = 2756060 | doi = 10.1016/j.cell.2009.06.046 }}</ref>
}}


[[Category:Drug]]
[[Category:Anti-inflammatory agents]]
[[Category:Anti-inflammatory agents]]
[[Category:Leukotriene antagonists]]
[[Category:Leukotriene antagonists]]
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[[Category:Carboxylic acids]]

Revision as of 14:20, 13 April 2015

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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC16H14N2O4
Molar mass298.293 g/mol
3D model (JSmol)
  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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 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

File:Amlexanoxsynthesis.png
Amlexanox synthesis:[16]

References

  1. ↑ "Amlexanox (Aphthasol®)". Retrieved 20 November 2013.
  2. ↑ Gonsalves WC, Chi AC, Neville BW (February 2007). "Common oral lesions: Part I. Superficial mucosal lesions". Am Fam Physician. 75 (4): 501–7. PMID 17323710.
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "Amlexanox". MedlinePlus. U.S. National Library of Medicine. February 2009. Retrieved 12 February 2013.
  4. ↑ 4.0 4.1 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. ↑ 6.0 6.1 Bailey J, McCarthy C, Smith RF (October 2011). "Clinical inquiry. What is the most effective way to treat recurrent canker sores?". J Fam Pract. 60 (10): 621–32. 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. ↑ 8.0 8.1 8.2 8.3 8.4 8.5 Bell J (2005). "Amlexanox for the treatment of recurrent aphthous ulcers". Clin Drug Investig. 25 (9): 555–66. doi:10.2165/00044011-200525090-00001. PMID 17532700.
  9. ↑ "Amlexanox". MeSH. U.S. National Library of Medicine. 2009. Retrieved 12 February 2013.
  10. ↑ Elad S, Epstein JB, von Bültzingslöwen I, Drucker S, Tzach R, Yarom N (March 2011). "Topical immunomodulators for management of oral mucosal conditions, a systematic review; Part II: miscellaneous agents". Expert Opin Emerg Drugs. 16 (1): 183–202. doi:10.1517/14728214.2011.528390. PMID 21244328.
  11. ↑ 11.0 11.1 11.2 Reilly SM, Chiang SH, Decker SJ, Chang L, Uhm M, Larsen MJ, Rubin JR, Mowers J, White NM, Hochberg I, Downes M, Yu RT, Liddle C, Evans RM, Oh D, Li P, Olefsky JM, Saltiel AR (February 2013). "An inhibitor of the protein kinases TBK1 and IKK-ɛ improves obesity-related metabolic dysfunctions in mice". Nat. Med. 19 (3): 313–21. doi:10.1038/nm.3082. PMID 23396211.
  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. ↑ Burgess JA, van der Ven PF, Martin M, Sherman J, Haley J (2008). "Review of over-the-counter treatments for aphthous ulceration and results from use of a dissolving oral patch containing glycyrrhiza complex herbal extract". J Contemp Dent Pract. 9 (3): 88–98. PMID 18335124.
  14. ↑ Kuteyi T, Okwundu CI (2012). Kuteyi, Teslim, ed. "Topical treatments for HIV-related oral ulcers". Cochrane Database Syst Rev. 1: CD007975. doi:10.1002/14651858.CD007975.pub2. PMID 22258979.
  15. ↑ Chiang SH, Bazuine M, Lumeng CN, Geletka LM, Mowers J, White NM, Ma JT, Zhou J, Qi N, Westcott D, Delproposto JB, Blackwell TS, Yull FE, Saltiel AR (September 2009). "The protein kinase IKKepsilon regulates energy balance in obese mice". Cell. 138 (5): 961–75. doi:10.1016/j.cell.2009.06.046. PMC 2756060. PMID 19737522.
  16. ↑ Template:Cite doi
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