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Merck

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

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About This Item

Empirical Formula (Hill Notation):
C28H28O3
CAS Number:
106685-40-9
Molecular Weight:
412.52
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD03106112

Product Name

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

SMILES string

O(C)c1c(cc(cc1)c5cc6c(cc(cc6)C(=O)O)cc5)C32CC4CC(C3)CC(C2)C4

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

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

Quality Level

100

Related Categories

Disclaimer

Toxicity: Standard Handling (A)

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 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.

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.

Preparation Note

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

Legal Information

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

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361d

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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