A7486

Adapalene

≥98% (HPLC)

• Synonym(s): 6-(4-Methoxy-3-tricyclo[3.3.1.1^3,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid, 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid, CD-271, Differin
• Empirical Formula (Hill Notation): C₂₈H₂₈O₃
• CAS Number: 106685-40-9
• Molecular Weight: 412.52
• NACRES: NA.77
• PubChem Substance ID: 329770932
• UNSPSC Code: 12352200
• MDL number: MFCD03106112
• Assay: ≥98% (HPLC)
• Form: powder
• Storage condition: desiccated

Properties

• 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

Description

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.

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).

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.

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.

Safety Information

• Pictograms: GHS08
• Signal Word: Warning
• Hazard Codes: H361d
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Repr. 2
• Storage Class: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable