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Merck
CN

A7486

Sigma-Aldrich

阿达帕林

≥98% (HPLC)

别名:

6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid, 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid, CD-271, Differin

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About This Item

经验公式(希尔记法):
C28H28O3
分子量:
412.52
MDL编号:
UNSPSC代码:
12352200
PubChem化学物质编号:
NACRES:
NA.77

质量水平

方案

≥98% (HPLC)

表单

powder

储存条件

desiccated

颜色

white to off-white

溶解性

DMSO: >10 mg/mL

储存温度

2-8°C

SMILES字符串

COc1ccc(cc1C23C[C@H]4C[C@H](C[C@H](C4)C2)C3)-c5ccc6cc(ccc6c5)C(O)=O

InChI

1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)/t17-,18+,19-,28-

InChI key

LZCDAPDGXCYOEH-AADAIPAGSA-N

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应用

Adapalen has been used as a supplement during culturing of peripheral blood mononuclear cells (PBMC).
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.

生化/生理作用

Adapalene is a synthetic derivative of naphthoic acid. It possesses retinoid activity. Adapalene is involved in regulating cellular keratinization and inflammatory process.
Adapalene, also referred as Differin, is a derivative of naphthoic acid. It is widely used for topical treatment of acne vulgaris. Adapalene elicits anti-inflammatory and retinoid-like activity. It also has a potential to regulate keratinization and differentiation of follicular epithelial cells.
Retinoic acid analogue that is a RARβ and RARγ agonist (AC50 values are 2.2, 9.3, 22 and > 1000 nM for RARβ, RARγ, RARα and RXRα receptors respectively). Inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro. Displays comedolytic activity. Its unique pharmacological properties make it superior to other retinoids for the treatment of acne.

特点和优势

This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

象形图

Health hazard

警示用语:

Warning

危险声明

危险分类

Repr. 2

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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分析证书(COA)

Lot/Batch Number

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A review of the use of adapalene for the treatment of acne vulgaris
Piskin S and Uzunali E
Therapeutics and Clinical Risk Management, 3(4), 621-621 (2007)
Benzimidazoles promote anti-TNF mediated induction of regulatory macrophages and enhance therapeutic efficacy in a murine model
Wildenberg M E, et al.
Journal of Crohn's & Colitis, 11(12) (2017)
The retinoic acid receptor (RAR) $\alpha$-specific agonist Am80 (tamibarotene) and other RAR agonists potently inhibit hepatitis B virus transcription from cccDNA
Nkongolo S, et al.
Antiviral Research, 168(4) (2019)
Nobukazu Hayashi et al.
The Journal of dermatology, 39(6), 511-515 (2011-12-16)
We conducted a randomized controlled trial in patients with acne vulgaris with moderate to severe inflammatory lesions. The patients were assigned to the following three treatment groups: group A received monotherapy with 0.1% topical adapalene gel for 4 weeks; group
Suleyman Piskin et al.
Therapeutics and clinical risk management, 3(4), 621-624 (2008-05-14)
Acne is a disease of the pilosebaceous unit with involving abnormalities in sebum production, microbial flora changes, abnormal keratinization, and inflammation. There are several therapeutic options like topical and systemic retinoids, antibiotics, and systemic hormonal drugs. The topical retinoids a

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