Adapalene

Base Information

• Chemical Name: Adapalene
• CAS No.: 106685-40-9
• Molecular Formula: C28H28O3
• Molecular Weight: 412.529
• Hs Code.: 2918992090
• European Community (EC) Number: 620-513-9
• UNII: 1L4806J2QF
• DSSTox Substance ID: DTXSID5046481
• Nikkaji Number: J399.566F
• Wikipedia: Adapalene
• Wikidata: Q352348
• NCI Thesaurus Code: C28989
• RXCUI: 60223
• Pharos Ligand ID: XQANG5395BZM
• Metabolomics Workbench ID: 42614
• ChEMBL ID: CHEMBL1265,CHEMBL4303650
• Mol file: 106685-40-9.mol

Synonyms:271, CD;6-(3-(1-adamantyl)-4-methoxyphenyl)-2-naphthoic acid;Adaferin;adapalene;CD 271;CD-271;CD271;Differin;Differine

Chemical Property of Adapalene

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 1.49E-15mmHg at 25°C
• Melting Point: 319-322 °C
• Refractive Index: 1.654
• Boiling Point: 606.3 °C at 760 mmHg
• PKA: 4.2(at 25℃)
• Flash Point: 205.9 °C
• PSA: 46.53000
• Density: 1.233 g/cm³
• LogP: 6.68140
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 7.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 412.20384475
• Heavy Atom Count: 31
• Complexity: 645

Purity/Quality:

99%, ^*data from raw suppliers

Adapalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5
• Recent ClinicalTrials: Effectivity and Safety of Combination Cream of Salicylic Acid, Aqua Posae Filiformis, Niacinamide, Lipohydroxy Acid, Procerad and Zinc PCA
• Recent EU Clinical Trials: A Phase 2, Multicenter, Randomized, Double-Blind, Vehicle-Controlled, Clinical Study to
• Recent NIPH Clinical Trials: Quantitative Determination of Nadifloxacin in Follicles of Acne Patients Treated by Topical Nadifloxacin With or Without Adapalene and Benzoyl Peroxide
• Uses: Retinoic acid analogs. Adapalene is an agonist of RARβ, and RARγ receptor. Adapalene inhibits cell proliferation and inducing apoptosis in colorectal cancer cells in vitro. Adapalene gel is an effective medication for treatment of acne. 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. Retinoid selective for retinoic acid receptor (RAR) subtypes ?and . Antiacne Retinoid selective for retinoic acid receptor (RAR) subtypes β and γ. Antiacne. anesthetic inhibits serotonin and noradrenaline reuptake antidepressant antimigraine therapeutic Acnetreatment
• Description: Adapalene is a synthetic retinoid and an agonist of retinoic acid receptors (RARs; Kds = 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.
• 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.
• Therapeutic Function: Antiacne

Technology Process of Adapalene

There total 26 articles about Adapalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

tert-butyl 6-(3-(1-adamantyl)-4-anisyl)-2-naphthoate → adapalene (106685-40-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 22h;

DOI:10.1016/j.cattod.2020.07.014

Reference yield: 99.0%

3-(1-adamantyl)-4-methoxyphenylboronic acid (459423-32-6) + 6-bromo-2-naphthoic acid (5773-80-8) → adapalene (106685-40-9)

Guidance literature:

3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid; With potassium carbonate; palladium 10% on activated carbon; In tetrahydrofuran; water; for 8h; Heating / reflux;

With hydrogenchloride; water; In tetrahydrofuran; for 1h; Product distribution / selectivity;

Reference yield: 97.0%

6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester (106685-41-0) → adapalene (106685-40-9)

Guidance literature:

6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester; With ethylene glycol; sodium hydroxide;

With hydrogenchloride; In water; Product distribution / selectivity;

upstream raw materials:

6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

4-bromo-phenol

1-adamanthanol

2-(1-adamantyl)-4-bromophenol

Downstream raw materials:

6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Refernces

• 1、 -. "Preparation method of adapalene". Paragraph 0004; 0007; 0010; 0017-0020. . Retrieved 2020/07/12.
• 2、 Ichii, Shun,Hamasaka, Go,Uozumi, Yasuhiro. "The Hiyama Cross-Coupling Reaction at Parts Per Million Levels of Pd: In Situ Formation of Highly Active Spirosilicates in Glycol Solvents". . p. 3850 - 3854. Retrieved 2019/11/11.