114825-M

Adapalene

A cell-permeable naphthoic acid compound that exhibits selective affinity and agonistic potency toward RARβ and RARγ over RARα.

• Synonym(s): Adapalene, CD271, RAR Agonist V, ADA, Differin, 6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid, CD 271, Differin, 6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid, CD 271, CD271, RAR Agonist V, ADA
• Empirical Formula (Hill Notation): C₂₈H₂₈O₃
• CAS Number: 106685-40-9
• Molecular Weight: 412.52
• MDL number: MFCD03106112
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥97% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: white
• solubility: DMSO: 12 mg/mL
• storage temp.: 2-8°C
• 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)
• InChI key: LZCDAPDGXCYOEH-UHFFFAOYSA-N

Description

General description

A cell-permeable naphthoic acid compound that exhibits selective affinity and agonistic potency toward RARβ and RARγ over RARα (Kd = 34, 130, and 1100 nM, respectively; AC₅₀ = 2.3, 9.3, and 22 nM, respectively, in COS-7-based reporter assays) without appreciable affinity toward cytosolic retinoic acid binding proteins CRABP I/II (Kd >>1 M) or detectable activity toward RXRα (AC₅₀ >1 M). The biological activity and pharmaceutical efficacy of ADA are generally shown to be superior to those of ATRA/Tretinoin both in vitro and in vivo.

A cell-permeable naphthoic acid compound that exhibits selective affinity and agonistic potency toward RARβ and RARγ over RARα (Kd = 34, 130, and 1100 nM, respectively; AC₅₀ = 2.3, 9.3, and 22 nM, respectively, in COS-7-based reporter assays) without appreciable affinity toward cytosolic retinoic acid binding proteins CRABP I/II (Kd >>1 µM) or detectable activity toward RXRα (AC₅₀ >1 µM). The biological activity and pharmaceutical efficacy of ADA are generally shown to be superior to those of ATRA/Tretinoin (Cat. No. 554720) both in vitro and in vivo.

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following initial thaw, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Irby, C.E., et al. 2008. J. Adolesc. Health43, 421.
Ocker, M., et al. 2003. Int. J. Cancer107, 453.
Kim, M.J., et al. 2000. J. Invest. Dermatol.114, 349.
Shroot, B., et al. 1997. J. Am. Acad. Dermatol.36, S96.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

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