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Amlexanox

Amlexanox structure

CAS No:
68302-57-8
Formula:
C16H14N2O4
Chemical Name:
Amlexanox
Synonyms:
5H-[1]Benzopyrano[2,3-b]pyridine-3-carboxylic acid,2-amino-7-(1-methylethyl)-5-oxo-;2-Amino-7-(1-methylethyl)-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid;AA 673;Amoxanox;Amlexanox;Elics;CHX 3673;Solfa;Aphtheal;Aphthasol;2-Amino-5-oxo-7-propan-2-ylchromeno[2,3-b]pyridine-3-carboxylic acid;2-Amino-7-isopropyl-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylicacid
Categories:
Active Pharmaceutical Ingredients > Antiallergic Drugs

Description

AmLexanox is a specific inhibitor of IKKε and TBK1, and inhibits the IKKε and TBK1 activity determined by MBP phosphorylation with an IC50 of approximately 1-2 μM.

Solid

Amlexanox is a pyridochromene-derived monocarboxylic acid having an amino substituent at the 2-position, an oxo substituent at the 5-position and an isopropyl substituent at the 7-position. It has a role as an anti-allergic agent, an anti-ulcer drug and a non-steroidal anti-inflammatory drug. It is a pyridochromene and a monocarboxylic acid.|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.|The physiologic effect of amlexanox is by means of Decreased Histamine Release.|Amlexanox is an anti-aphthous ulcer drug. Amlexanox inhibits the synthesis and release of inflammatory mediators, including leukotrienes and histamine, from mast cells, neutrophils, and mononuclear cells. Amlexanox also acts as a leukotriene D4 antagonist and a phosphodiesterase inhibitor. Amlexanox decreases the time ulcers take to heal as well as the pain associated with the ulcers.

Amlexanox Basic Attributes

Molecular Weight：

298.29300

Exact Mass：

298.29

UNII：

BRL1C2459K

DSSTox ID：

DTXSID2022595

NCI Thesaurus Code：

C47395

ATC Code：

A - Alimentary tract and metabolism|R - Respiratory system

HScode：

2934999090

Characteristics

PSA：

106.42000

XLogP3：

3.1

Appearance：

white crystalline solid

Density：

1.408 g/cm3

Melting Point：

>300 °C

Boiling Point：

570ºC at 760 mmHg

Flash Point：

298.5ºC

Refractive Index：

1.668

Water Solubility：

1.46e-01 g/L

Storage Conditions：

Store in original container in a cool dark place.

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R22; R36/37/38

safety instructions：

S26; S36

RTECS Number：

XZ3012000

Marks：

Xn; Xi

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

H302

Drug Information

Drug Indication：

Used as a paste in the mouth to treat aphthous ulcers (canker sores).|FDA Label

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.

MeSH：

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)

Absorption：

No significant absorption directly through the active ulcer. Most of the systemic absorption is via the gastrointestinal tract.

Metabolism/Metabolites：

Metabolized to hydroxylated and conjugated metabolites.

Biological Half-Life：

Elimination half-life is 3.5 ± 1.1 hours.

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.

MeSH Entry Terms：

2-amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3b)pyridine-3-carboxylic acid

Amlexanox Use and Manufacturing

Uses

Inhibits release of allergic mediators from mast cells. Antiallergic; antiasthmaticIt has histamine free reaction inhibitory effect, leukotriene production inhibitory effect and anti-leukotriene effect, resulting in anti-asthma effects. For the treatment of bronchial asthma and allergic rhinitis. Used to treat oral ulcers Antihistamines have a high degree of selectivity for peripheral nerve H1 receptors, a strong effect and a long time. Used for allergic arthritis and allergic rhinitis. National Class II anti-allergic new drug, used to relieve nasal and non-nasal symptoms of seasonal allergic rhinitis and relieve chronic urticaria

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:298.29
XLogP3:3.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:298.09535693
Monoisotopic Mass:298.09535693
Topological Polar Surface Area:103
Heavy Atom Count:22
Complexity:467
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

The mechanism of action is mainly to inhibit lipopolysaccharide synthase, inhibit the production of leukotrienes and anti-leukotrienes, and accelerate the healing of aphthous ulcers through anti-allergic and anti-inflammatory effects.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Amlexanox paste
Ingredients	Main ingredients: Amlexanox.
Indication	In vitro studies have shown that amlexanox is an effective inhibitor of the formation and release of inflammatory mediators (histamine and leukotrienes) in mast cells, neutrophils and monocytes. Oral administration to animals has shown that amlexanox has anti-allergic and anti-inflammatory effects, and inhibits immediate and delayed allergic reactions.
Specifications	5g: 0.25g; 2g: 0.1g
Manufacturer	Shandong LINUO Pharmaceutical Company Limited

Amlexanox
Manufacturer	Sichuan Xuhui Pharmaceutical Co., Ltd.

Amlexanox paste
Ingredients	Main ingredients: Amlexanox.
Indication	In vitro studies have shown that amlexanox is an effective inhibitor of the formation and release of inflammatory mediators (histamine and leukotrienes) in mast cells, neutrophils and monocytes. Oral administration to animals has shown that amlexanox has anti-allergic and anti-inflammatory effects, and inhibits immediate and delayed allergic reactions.
Specifications	5g:0.25g
Manufacturer	Sichuan Xuhui Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

Shandong Keyuan Pharmaceutical Co., Ltd.

China
Active
Sichuan Xuhui Pharmaceutical Co., Ltd.

China
Active
CHIA TAI Tianqing Pharmaceutical Group Co., Ltd.

China
Active

See More Registered Holders

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