Adapalene - Moligand™, ≥98% , Agonist of Retinoic acid receptor-αAgonist of Retinoic acid receptor-βAgonist of Retinoic acid receptor-γ, CAS No.106685-40-9, Agonist of Retinoic acid receptor-αAgonist of Retinoic acid receptor-βAgonist of Retinoic acid receptor-γ

CAS: 106685-40-9 Cat. No.: A120006 分子式: C₂₈H₂₈O₃ 分子量: 412.52 EC番号: 620-513-9

GRADE & PURITY Moligand™, ≥98%

Synonyms

6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid | Adapaleno [INN-Spanish] | CD271 | CD-271 | STL453114 | UNII-1L4806J2QF | Adaferin | Adapaleno (INN-Spanish) | AKOS015895391 | Differine | HMS3715H16 | SR-01000942194 | Tox21

Storage

Store at 2-8°C

Shipped In

Wet ice

概要

Adapalene is a dual RAR and RXR agonist, used in the treatment of acne.
Adapalene, a retinoic acid analogue, is a RARβ and RARγ agonist. Adapalene inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro. Adapalene gel is an efficacious treatment for acne vulgaris.

Specifications

同義語

6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid | Adapaleno [INN-Spanish] | CD271 | CD-271 | STL453114 | UNII-1L4806J2QF | Adaferin | Adapaleno (INN-Spanish) | AKOS015895391 | Differine | HMS3715H16 | SR-01000942194 | Tox21

仕様と純度

Moligand™, ≥98%

生化学的・生理学的メカニズム

Retinoic acid analog that is a RARβand RARγagonist (AC50values are 2.2, 9.3, 22 and > 1000 nM for RARβ, RARγ, RARαand RXRαreceptors respectively). Inhibits proliferation and induces apoptosis in colorectal cancer cellin vitro. Displays comedolytic activit

保管条件

Store at 2-8°C

入荷

Wet ice

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

等級

Moligand™

アクションタイプ

AGONIST

作用メカニズム

Agonist of Retinoic acid receptor-αAgonist of Retinoic acid receptor-βAgonist of Retinoic acid receptor-γ

純度

≥98%

名前と識別子

• パブケム・シド: 488183399
• パブケム・シド・ウル: https://pubchem.ncbi.nlm.nih.gov/substance/488183399
• カノニカル・スマイル: COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5
• IUPAC Name: 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
• InChIKey: LZCDAPDGXCYOEH-UHFFFAOYSA-N
• 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)
• 異性体SMILES: COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5
• RTECS: QJ1987000
• 分子量: 412.52
• Reaxy-Rn: 7393980
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7393980&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • 分類 Prenol lipids
      • Subclass Retinoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• 分類: Prenol lipids
• Subclass: Retinoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Retinoids
• Alternative Parents: Phenylnaphthalenes Naphthalenecarboxylic acids Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Adapalene - Phenylnaphthalene - 2-naphthalenecarboxylic acid - 2-naphthalenecarboxylic acid or derivatives - Naphthalene - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - Alkyl aryl ether - Monocyclic benzene moiety - Benzenoid - Monocarboxylic acid or derivatives - Ether - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxygen compound - Organic oxide - Organooxygen compound - Aromatic homopolycyclic compound
• 説明: This compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
• External Descriptors: monocarboxylic acid - adamantanes

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

関連ターゲット（人間）

RARG Tclin Retinoic acid receptor gamma (2 Activities)

Discover Target: RARG

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

RARB Tclin Retinoic acid receptor beta (4 Activities)

Discover Target: RARB

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

RARA Tclin Retinoic acid receptor alpha (2 Activities)

Discover Target: RARA

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GLRA1 Tclin Glycine receptor subunit alpha-1 (1 Activities)

Discover Target: GLRA1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

化学的性質と物理的性質

• 溶解度: Solvent:DMSO, Max Conc. mg/mL: 10.31, Max Conc. mM: 25
• 感度: Moisture &Heat sensitive
• 融点（°C）: 301℃
• 分子量: 412.500 g/mol
• XLogP3: 7.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 412.204 Da
• Monoisotopic Mass: 412.204 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 644.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

参考文献

1. Xin Pan, Pei Liu, Hao Wei, Yushan Zhao, Tian Wang, Yejun Zhang, Xinyuan Wang, Xiaofang Hu, Xiaoli Ma, Yi-wei Wang, Sheng Guo, Yuanyuan Wang, Jin-Ao Duan.  (2025)  Ultrasound-assisted DMSO method for rapid starch gel preparation: process and biomedical applications.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.166488]

2. Yan Deng, Hao Cheng, Ji Zhu, Yue Jiang, Hongwu Sun, Guocheng Li, Jing Wei, Ruoyi Xue, Rang Feng, Jingwen Cao, Wenkang Yu, Yalan Wang, Mingqi Xu, Quanming Zou, Haibo Li.  (2025)  Tamibarotene-Loaded Nanoemulsion Incorporating Toll-like Receptor 2/6 Agonist as an Intramuscular Adjuvant System Enhances Gastrointestinal Mucosal Immunity.  ACS Nano,      [PMID:40376869] [10.1021/acsnano.5c00563]