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68302-57-8 molecular structure
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2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid

ChemBase ID: 898
Molecular Formular: C16H14N2O4
Molecular Mass: 298.29336
Monoisotopic Mass: 298.09535694
SMILES and InChIs

SMILES:
o1c2c(cc(C(C)C)cc2)c(=O)c2c1nc(N)c(c2)C(=O)O
Canonical SMILES:
CC(c1ccc2c(c1)c(=O)c1c(o2)nc(c(c1)C(=O)O)N)C
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)
InChIKey:
SGRYPYWGNKJSDL-UHFFFAOYSA-N

Cite this record

CBID:898 http://www.chembase.cn/molecule-898.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid
IUPAC Traditional name
aphthasol
amlexanox
Brand Name
Amlenanox
Amoxanox
Aphthasol
Elics
Solfa
OraDisc
Synonyms
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
2-Amino-7-isopropyl-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylic acid
Amlexanox [USAN:INN:JAN]
Amlexanoxo [Spanish]
Amlexanoxum [Latin]
amlexanox
Amlexanox
CAS Number
68302-57-8
MDL Number
MFCD00864790
PubChem SID
46504508
160964361
PubChem CID
2161

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
LogD (pH = 5.5) 2.4327643  LogD (pH = 7.4) 0.6937152 
Log P 3.654549  Molar Refractivity 81.4338 cm3
Polarizability 30.038202 Å3 Polar Surface Area 102.51 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Acid pKa 4.3032084  H Acceptors
H Donor
Log P 2.76  LOG S -3.31 
Solubility (Water) 1.46e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol (Sparingly) expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
>300°C (decx.) expand Show data source
Hydrophobicity(logP)
4.1 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Purity
95+% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB01025 external link
Item Information
Drug Groups approved; investigational
Description 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.
Indication Used as a paste in the mouth to treat aphthous ulcers (canker sores).
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.
Affected Organisms
Humans and other mammals
Biotransformation Metabolized to hydroxylated and conjugated metabolites.
Absorption No significant absorption directly through the active ulcer. Most of the systemic absorption is via the gastrointestinal tract.
Half Life Elimination half-life is 3.5 ± 1.1 hours.
References
Bell J: Amlexanox for the treatment of recurrent aphthous ulcers. Clin Drug Investig. 2005;25(9):555-66. [Pubmed]
External Links
Drugs.com
Toronto Research Chemicals - A633410 external link
Inhibits release of allergic mediators from mast cells. Antiallergic; antiasthmatic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Bell J: Amlexanox for the treatment of recurrent aphthous ulcers. Clin Drug Investig. 2005;25(9):555-66. Pubmed
  • • Rankov, G., et al.: Ophthalmic Res., 22, 359 (1990)
  • • Greer, R.O., et al.: J. Oral Mxillofac. Surg., 51, 243 (1990)
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PATENTS

PATENTS

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INTERNET

INTERNET

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