A7486

Adapalen

≥98% (HPLC)

• Synonym(e): 6-(4-Methoxy-3-tricyclo[3.3.1.1^3,7]dec-1-ylphenyl)-2-naphthalincarbonsäure, 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoesäure, CD-271, Differin
• Empirische Formel (Hill-System): C₂₈H₂₈O₃
• CAS-Nummer: 106685-40-9
• Molekulargewicht: 412.52
• NACRES: NA.77
• PubChem Substance ID: 329770932
• UNSPSC Code: 12352200
• MDL number: MFCD03106112
• Assay: ≥98% (HPLC)
• Form: powder
• Storage condition: desiccated

Eigenschaften

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• storage condition: desiccated
• color: white to off-white
• solubility: DMSO: >10 mg/mL
• storage temp.: 2-8°C
• SMILES string: 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

Beschreibung

Application

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.

Biochem/physiol Actions

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.

Retinsäure-Analogon, das ein RARβ- und RARγ-Agonist ist (AC50-Werte betragen 2.2, 9.3, 22 und > 1000 nM für RARβ-, RARγ-, RARα- bzw. RXRα-Rezeptoren)

Retinsäure-Analogon, das ein RARβ- und RARγ-Agonist ist (AC50-Werte betragen 2.2, 9.3, 22 und > 1000 nM für RARβ-, RARγ-, RARα- bzw. RXRα-Rezeptoren). Hemmt in vitro die Proliferation und induziert Apoptose in kolorektalen Krebszellen. Zeigt komedolytische Wirkung. Durch seine einzigartigen pharmakologischen Eigenschaften ist es besser als andere Retinoide zur Behandlung von Akne geeignet.

Adapalene is a synthetic derivative of naphthoic acid. It possesses retinoid activity. Adapalene is involved in regulating cellular keratinization and inflammatory process.

Features and Benefits

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.

Sicherheitshinweise

• pictograms: GHS08
• signalword: Warning
• hcodes: H361d
• pcodes: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Repr. 2
• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable