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

• ChemBase编号: 898
• 分子式: C16H14N2O4
• 平均质量: 298.29336
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid
• IUPAC传统名: aphthasol; amlexanox
• 商标名: Amlenanox; Amoxanox; Aphthasol; Elics; Solfa; OraDisc
• 别名: 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

登记号

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

理论计算性质

JChem

• LogD (pH = 5.5): 2.4327643
• LogD (pH = 7.4): 0.6937152
• Log P: 3.654549
• 摩尔折射率: 81.4338 cm^3
• 极化性: 30.038202 Å^3
• 极化表面积: 102.51 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true
• Acid pKa: 4.3032084
• 质子受体: 5
• 质子供体: 2

ALOGPS 2.1

• Log P: 2.76
• LOG S: -3.31
• 溶解度: 1.46e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; Methanol (Sparingly)
• 外观: White to Off-White Solid
• 熔点: >300°C (decx.)
• 疏水性(logP): 4.1

安全信息

• 保存条件: -20°C Freezer

产品相关信息

• 纯度: 95+%

详细说明

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.

参考文献

• 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)