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 Peso molecular: 412.52 Número EC: 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

Descripción general

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

Sinónimos

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

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

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

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Tipo de acción

AGONIST

Mecanismo de acción

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

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 488183399
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488183399
• Sonrisas canónicas: 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)
• Isómeros 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
• Peso molecular: 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
    • Clase Prenol lipids
      • Subclass Retinoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: 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
• Descripción: 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

Objetivos asociados (humanos)

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)

Propiedades químicas y físicas

• Solubilidad: Solvent:DMSO, Max Conc. mg/mL: 10.31, Max Conc. mM: 25
• Sensibilidad: Moisture &Heat sensitive
• Punto de fusión (°C): 301℃
• Peso molecular: 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

Referencias

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]