Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Amlexanox
- DrugBank Accession Number
- DB01025
- Background
Amlexanox is an antiallergic drug, clinically effective for atopic diseases, especially allergic asthma and rhinitis. Amlexanox as a topical paste is a well tolerated treatment of recurrent aphthous ulcers. Recurrent aphthous ulcer (RAU) is the most prevalent oral mucosal disease in humans, estimated to affect between 5% and 50% of the general population.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Withdrawn
- Structure
Structure for Amlexanox (DB01025)
- Weight
- Average: 298.2934
Monoisotopic: 298.095356946 - Chemical Formula
- C16H14N2O4
- Synonyms
- 2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3-b)pyridine-3-carboxylic acid
- Amlexanox
- Amlexanoxo
- Amlexanoxum
- Amoxanox
- External IDs
- AA-673
- CHX 3673
- CHX-3673
Pharmacology
- Indication
Used as a paste in the mouth to treat aphthous ulcers (canker sores).
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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.
- 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.
Target Actions Organism AHeat shock protein HSP 90-alpha inhibitorHumans UProtein S100-A12 antagonistHumans UProtein S100-A13 antagonistHumans UInterleukin-3 antagonistHumans UFibroblast growth factor 1 inhibitorHumans - Absorption
No significant absorption directly through the active ulcer. Most of the systemic absorption is via the gastrointestinal tract.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Metabolized to hydroxylated and conjugated metabolites.
- Route of elimination
Not Available
- Half-life
Elimination half-life is 3.5 ± 1.1 hours.
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.No interactions found.
- Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Aphthasol / Elics / OraDisc A / Solfa
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apthera Paste 5 % Oral Pharmascience Inc Not applicable Not applicable Canada 
Categories
- ATC Codes
- A01AD07 — Amlexanox
- A01AD — Other agents for local oral treatment
- A01A — STOMATOLOGICAL PREPARATIONS
- A01 — STOMATOLOGICAL PREPARATIONS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as chromeno[2,3-b]pyridine-5-ones. These are compounds containing a Chromeno[2,3-b]pyridine moiety that carries an oxo group at the 5-position.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzopyrans
- Sub Class
- 1-benzopyrans
- Direct Parent
- Chromeno[2,3-b]pyridine-5-ones
- Alternative Parents
- Chromenopyridines / Pyranopyridines / Pyridinecarboxylic acids / Pyranones and derivatives / Aminopyridines and derivatives / Benzenoids / Imidolactams / Vinylogous amides / Heteroaromatic compounds / Amino acids show 9 more
- Substituents
- Amine / Amino acid / Amino acid or derivatives / Aminopyridine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxylic acid / Carboxylic acid derivative / Chromeno[2,3-b]pyridine-5-one show 20 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- monocarboxylic acid, pyridochromene (CHEBI:31205)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- BRL1C2459K
- CAS number
- 68302-57-8
- InChI Key
- SGRYPYWGNKJSDL-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid
- SMILES
- CC(C)C1=CC2=C(OC3=NC(N)=C(C=C3C2=O)C(O)=O)C=C1
References
- General References
- Bell J: Amlexanox for the treatment of recurrent aphthous ulcers. Clin Drug Investig. 2005;25(9):555-66. [Article]
- External Links
- Human Metabolome Database
- HMDB0015160
- KEGG Drug
- D01828
- PubChem Compound
- 2161
- PubChem Substance
- 46504508
- ChemSpider
- 2076
- BindingDB
- 357857
- 46307
- ChEBI
- 31205
- ChEMBL
- CHEMBL1096
- ZINC
- ZINC000000000928
- Therapeutic Targets Database
- DAP000321
- PharmGKB
- PA164745310
- PDBe Ligand
- ANW
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Amlexanox
- PDB Entries
- 2kot / 4wbo / 5w5v
- FDA label
- Download (129 KB)
- MSDS
- Download (79.7 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data2 Completed Treatment Fatty Liver, Non-alcoholic Fatty Liver Disease, NAFLD / Obesity / Type 2 Diabetes Mellitus 1 somestatus stop reason just information to hide 2 Completed Treatment Oral Mucositis 1 somestatus stop reason just information to hide 2 Terminated Treatment Fatty Liver, Non-alcoholic Fatty Liver Disease, NAFLD / Obesity / Type 2 Diabetes Mellitus 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Block Drug Corp.
- Contract Pharm
- Discus Dental
- Uluru Inc.
- Dosage Forms
Form Route Strength Paste Oral 5 % - Prices
Unit description Cost Unit Aphthasol 5% Paste 3 gm Tube 29.99USD tube Aphthasol 5% paste 7.36USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5362737 No 1994-11-08 2011-11-08 US 
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 4.1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.146 mg/mL ALOGPS logP 2.76 ALOGPS logP 3.65 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 4.31 Chemaxon pKa (Strongest Basic) 1.87 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 102.51 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 81.43 m3·mol-1 Chemaxon Polarizability 30.82 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7639 Blood Brain Barrier - 0.5689 Caco-2 permeable - 0.6574 P-glycoprotein substrate Non-substrate 0.5954 P-glycoprotein inhibitor I Non-inhibitor 0.9502 P-glycoprotein inhibitor II Non-inhibitor 0.9669 Renal organic cation transporter Non-inhibitor 0.9624 CYP450 2C9 substrate Non-substrate 0.82 CYP450 2D6 substrate Non-substrate 0.8797 CYP450 3A4 substrate Non-substrate 0.6051 CYP450 1A2 substrate Non-inhibitor 0.671 CYP450 2C9 inhibitor Non-inhibitor 0.8017 CYP450 2D6 inhibitor Non-inhibitor 0.9244 CYP450 2C19 inhibitor Non-inhibitor 0.7582 CYP450 3A4 inhibitor Non-inhibitor 0.922 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9501 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.8727 Biodegradation Not ready biodegradable 0.9071 Rat acute toxicity 1.5062 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9942 hERG inhibition (predictor II) Non-inhibitor 0.8609
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 183.7148948 predictedDarkChem Lite v0.1.0 [M-H]- 183.9836948 predictedDarkChem Lite v0.1.0 [M-H]- 175.85703 predictedDeepCCS 1.0 (2019) [M+H]+ 183.6914948 predictedDarkChem Lite v0.1.0 [M+H]+ 184.5584948 predictedDarkChem Lite v0.1.0 [M+H]+ 178.23915 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.9412948 predictedDarkChem Lite v0.1.0 [M+Na]+ 183.9879948 predictedDarkChem Lite v0.1.0 [M+Na]+ 186.21442 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Undergoes a functional cycle that is linked to its ATPase activity which is essential for its chaperone activity. This cycle probably induces conformational changes in the client proteins, thereby causing their activation. Interacts dynamically with various co-chaperones that modulate its substrate recognition, ATPase cycle and chaperone function (PubMed:11274138, PubMed:12526792, PubMed:15577939, PubMed:15937123, PubMed:27353360, PubMed:29127155). Engages with a range of client protein classes via its interaction with various co-chaperone proteins or complexes, that act as adapters, simultaneously able to interact with the specific client and the central chaperone itself (PubMed:29127155). Recruitment of ATP and co-chaperone followed by client protein forms a functional chaperone. After the completion of the chaperoning process, properly folded client protein and co-chaperone leave HSP90 in an ADP-bound partially open conformation and finally, ADP is released from HSP90 which acquires an open conformation for the next cycle (PubMed:26991466, PubMed:27295069). Plays a critical role in mitochondrial import, delivers preproteins to the mitochondrial import receptor TOMM70 (PubMed:12526792). Apart from its chaperone activity, it also plays a role in the regulation of the transcription machinery. HSP90 and its co-chaperones modulate transcription at least at three different levels (PubMed:25973397). In the first place, they alter the steady-state levels of certain transcription factors in response to various physiological cues (PubMed:25973397). Second, they modulate the activity of certain epigenetic modifiers, such as histone deacetylases or DNA methyl transferases, and thereby respond to the change in the environment (PubMed:25973397). Third, they participate in the eviction of histones from the promoter region of certain genes and thereby turn on gene expression (PubMed:25973397). Binds bacterial lipopolysaccharide (LPS) and mediates LPS-induced inflammatory response, including TNF secretion by monocytes (PubMed:11276205). Antagonizes STUB1-mediated inhibition of TGF-beta signaling via inhibition of STUB1-mediated SMAD3 ubiquitination and degradation (PubMed:24613385). Mediates the association of TOMM70 with IRF3 or TBK1 in mitochondrial outer membrane which promotes host antiviral response (PubMed:20628368, PubMed:25609812)
- Specific Function
- ATP binding
- Gene Name
- HSP90AA1
- Uniprot ID
- P07900
- Uniprot Name
- Heat shock protein HSP 90-alpha
- Molecular Weight
- 84659.015 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- S100A12 is a calcium-, zinc- and copper-binding protein which plays a prominent role in the regulation of inflammatory processes and immune response. Its pro-inflammatory activity involves recruitment of leukocytes, promotion of cytokine and chemokine production, and regulation of leukocyte adhesion and migration. Acts as an alarmin or a danger associated molecular pattern (DAMP) molecule and stimulates innate immune cells via binding to receptor for advanced glycation endproducts (AGER). Binding to AGER activates the MAP-kinase and NF-kappa-B signaling pathways leading to production of pro-inflammatory cytokines and up-regulation of cell adhesion molecules ICAM1 and VCAM1. Acts as a monocyte and mast cell chemoattractant. Can stimulate mast cell degranulation and activation which generates chemokines, histamine and cytokines inducing further leukocyte recruitment to the sites of inflammation. Can inhibit the activity of matrix metalloproteinases; MMP2, MMP3 and MMP9 by chelating Zn(2+) from their active sites. Possesses filariacidal and filariastatic activity. Calcitermin possesses antifungal activity against C.albicans and is also active against E.coli and P.aeruginosa but not L.monocytogenes and S.aureus
- Specific Function
- calcium ion binding
- Gene Name
- S100A12
- Uniprot ID
- P80511
- Uniprot Name
- Protein S100-A12
- Molecular Weight
- 10574.975 Da
References
- Shishibori T, Oyama Y, Matsushita O, Yamashita K, Furuichi H, Okabe A, Maeta H, Hata Y, Kobayashi R: Three distinct anti-allergic drugs, amlexanox, cromolyn and tranilast, bind to S100A12 and S100A13 of the S100 protein family. Biochem J. 1999 Mar 15;338 ( Pt 3):583-9. [Article]
- Okada M, Tokumitsu H, Kubota Y, Kobayashi R: Interaction of S100 proteins with the antiallergic drugs, olopatadine, amlexanox, and cromolyn: identification of putative drug binding sites on S100A1 protein. Biochem Biophys Res Commun. 2002 Apr 12;292(4):1023-30. [Article]
- Kishimoto K, Kaneko S, Ohmori K, Tamura T, Hasegawa K: Olopatadine suppresses the migration of THP-1 monocytes induced by S100A12 protein. Mediators Inflamm. 2006;2006(1):42726. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Plays a role in the export of proteins that lack a signal peptide and are secreted by an alternative pathway. Binds two calcium ions per subunit. Binds one copper ion. Binding of one copper ion does not interfere with calcium binding. Required for the copper-dependent stress-induced export of IL1A and FGF1. The calcium-free protein binds to lipid vesicles containing phosphatidylserine, but not to vesicles containing phosphatidylcholine (By similarity)
- Specific Function
- calcium ion binding
- Gene Name
- S100A13
- Uniprot ID
- Q99584
- Uniprot Name
- Protein S100-A13
- Molecular Weight
- 11471.095 Da
References
- Shishibori T, Oyama Y, Matsushita O, Yamashita K, Furuichi H, Okabe A, Maeta H, Hata Y, Kobayashi R: Three distinct anti-allergic drugs, amlexanox, cromolyn and tranilast, bind to S100A12 and S100A13 of the S100 protein family. Biochem J. 1999 Mar 15;338 ( Pt 3):583-9. [Article]
- Landriscina M, Prudovsky I, Mouta Carreira C, Soldi R, Tarantini F, Maciag T: Amlexanox reversibly inhibits cell migration and proliferation and induces the Src-dependent disassembly of actin stress fibers in vitro. J Biol Chem. 2000 Oct 20;275(42):32753-62. [Article]
- Okada M, Tokumitsu H, Kubota Y, Kobayashi R: Interaction of S100 proteins with the antiallergic drugs, olopatadine, amlexanox, and cromolyn: identification of putative drug binding sites on S100A1 protein. Biochem Biophys Res Commun. 2002 Apr 12;292(4):1023-30. [Article]
- Matsunaga H, Ueda H: Evidence for serum-deprivation-induced co-release of FGF-1 and S100A13 from astrocytes. Neurochem Int. 2006 Aug;49(3):294-303. Epub 2006 Mar 7. [Article]
- Mouta Carreira C, LaVallee TM, Tarantini F, Jackson A, Lathrop JT, Hampton B, Burgess WH, Maciag T: S100A13 is involved in the regulation of fibroblast growth factor-1 and p40 synaptotagmin-1 release in vitro. J Biol Chem. 1998 Aug 28;273(35):22224-31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Cytokine secreted predominantly by activated T-lymphocytes as well as mast cells and osteoblastic cells that controls the production and differentiation of hematopoietic progenitor cells into lineage-restricted cells (PubMed:2556442). Stimulates also mature basophils, eosinophils, and monocytes to become functionally activated (PubMed:10779277, PubMed:32889153). In addition, plays an important role in neural cell proliferation and survival (PubMed:23226269). Participates as well in bone homeostasis and inhibits osteoclast differentiation by preventing NF-kappa-B nuclear translocation and activation (PubMed:12816992). Mechanistically, exerts its biological effects through a receptor composed of IL3RA subunit and a signal transducing subunit IL3RB (PubMed:29374162). Receptor stimulation results in the rapid activation of JAK2 kinase activity leading to STAT5-mediated transcriptional program (By similarity). Alternatively, contributes to cell survival under oxidative stress in non-hematopoietic systems by activating pathways mediated by PI3K/AKT and ERK (PubMed:27862234)
- Specific Function
- cytokine activity
- Gene Name
- IL3
- Uniprot ID
- P08700
- Uniprot Name
- Interleukin-3
- Molecular Weight
- 17232.905 Da
References
- Urisu A, Iimi K, Kondo Y, Horiba F, Masuda S, Tsuruta M, Yazaki T, Torii S: [Inhibitory action amlexanox on interleukin-3-induced enhancement of histamine releasability of human leukocytes]. Arerugi. 1990 Oct;39(10):1448-54. [Article]
- Nagai H, Suda H, Iwama T, Daikoku M, Yanagihara Y, Koda A: Effect of NZ-107, a newly synthesized pyridazinone derivative, on antigen-induced contraction of human bronchial strips and histamine release from human lung fragments or leukocytes. Int Arch Allergy Immunol. 1992;98(1):57-63. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Plays an important role in the regulation of cell survival, cell division, angiogenesis, cell differentiation and cell migration. Functions as a potent mitogen in vitro. Acts as a ligand for FGFR1 and integrins. Binds to FGFR1 in the presence of heparin leading to FGFR1 dimerization and activation via sequential autophosphorylation on tyrosine residues which act as docking sites for interacting proteins, leading to the activation of several signaling cascades. Binds to integrin ITGAV:ITGB3. Its binding to integrin, subsequent ternary complex formation with integrin and FGFR1, and the recruitment of PTPN11 to the complex are essential for FGF1 signaling. Induces the phosphorylation and activation of FGFR1, FRS2, MAPK3/ERK1, MAPK1/ERK2 and AKT1 (PubMed:18441324, PubMed:20422052). Can induce angiogenesis (PubMed:23469107)
- Specific Function
- fibroblast growth factor receptor binding
- Gene Name
- FGF1
- Uniprot ID
- P05230
- Uniprot Name
- Fibroblast growth factor 1
- Molecular Weight
- 17459.58 Da
References
- Rajalingam D, Kumar TK, Soldi R, Graziani I, Prudovsky I, Yu C: Molecular mechanism of inhibition of nonclassical FGF-1 export. Biochemistry. 2005 Nov 29;44(47):15472-9. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:23