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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 68302-57-8
• MDL Number: MFCD00864790
• PubChem SID: 46504508; 160964361
• PubChem CID: 2161

CALCULATED PROPERTIES

JChem

• LogD (pH = 5.5): 2.4327643
• LogD (pH = 7.4): 0.6937152
• Log P: 3.654549
• Molar Refractivity: 81.4338 cm^3
• Polarizability: 30.038202 Å^3
• Polar Surface Area: 102.51 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 4.3032084
• H Acceptors: 5
• H Donor: 2

ALOGPS 2.1

• Log P: 2.76
• LOG S: -3.31
• Solubility (Water): 1.46e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: White to Off-White Solid
• Melting Point: >300°C (decx.)
• Hydrophobicity(logP): 4.1

Safety Information

• Storage Condition: -20°C Freezer

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB01025

• 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

Inhibits release of allergic mediators from mast cells. Antiallergic; antiasthmatic.

REFERENCES

• 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)