Adapalene

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• 그림문자(GHS)

  

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Adapalene MSDS

• 6-[3-(1-Adamantyl)-4-methoxy-phenyl]naphthalene-2-carboxylic acid

Adapalene 화학적 특성, 용도, 생산

• 개요

  Adapalene is a synthetic retinoid and an agonist of retinoic acid receptors (RARs; K_ds = 1,100, 34, and 130 nM for RARα, RARβ, and RARγ, respectively). It inhibits growth and differentiation of sebocytes in a concentration-dependent manner in primary rat preputial cell culture. Adapalene (10 μM) completely inhibits the activity of soybean 15-lipoxygenase (15-LOX) in an enzyme assay and inhibits the 5- and 15-LOX pathways in human blood polymorphonuclear leukocytes (PMNs). It reduces the protein levels of toll-like receptor 2 (TLR2) and IL-10 in skin explants isolated from patients with acne and healthy controls in a concentration-dependent manner but increases the expression of the antigen-presenting protein CD1d in acne skin explants while decreasing it in control explants. It inhibits inflammation in rodent models of ear edema induced by arachidonic acid and carrageenan-induced paw edema. Adapalene (100 μM) also induces apoptosis and inhibits proliferation of CC-531, HT-29, and LoVo colon cancer cells and reduces tumor growth in a DLD-1 colon cancer nude mouse xenograft model in a dose-dependent manner. Formulations containing adapalene have been used in the treatment of acne vulgaris.

• 화학적 성질

  White Crystalline Solid

• 용도

  Adapalene has been used as a retinoic acid receptor (RAR) agonist to study its effects on inhibiting transcription of hepatitis B virus in covalently closed circular DNA (cccDNA). It has also been used as a component to culture mixed lymphocyte reactions (MLR) to study its effects on isolated macrophages.

• Indications

  Adapalene (Differin) is a polyaromatic retinoidlike compound that binds to specific retinoic acid nuclear receptors and is thought to normalize the differentiation of keratinocytes in the sebaceous acroinfundibulum. Adapelene is indicated for topical treatment of acne. Minor local irritation is a common, usually tolerable side effect. In contrast to other drugs of the retinoid group, adapalene has not been shown to be teratogenic in rodents. However, since adequate human studies are lacking, its use in pregnant women should be discouraged until further information is available.

• 정의

  ChEBI: A naphthoic acid that is CD437 in which the phenolic hydroxy group has been converted to its methyl ether.

• 일반 설명

  Adapalene is a third-generation synthetic retinoid and a highly lipophilic compound derived from naphthoic acid. It is widely used in the treatment of acne.

• 생물학적 활성

  Retinoic acid analog that is a RAR β and RAR γ agonist (AC 50 values are 2.2, 9.3, 22 and > 1000 nM for RAR β , RAR γ , RAR α and RXR α receptors respectively). Inhibits proliferation and induces apoptosis in colorectal cancer cell in vitro . Displays comedolytic activity.

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