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Merck
CN

A7486

Adapalene

≥98% (HPLC)

Synonym(s):

6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid, 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid, CD-271, Differin

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About This Item

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
Quality level:
100
Storage condition:
desiccated

Key Documents

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form

powder

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-

SMILES string

COc1ccc(cc1C23C[C@H]4C[C@H](C[C@H](C4)C2)C3)-c5ccc6cc(ccc6c5)C(O)=O

InChI key

LZCDAPDGXCYOEH-AADAIPAGSA-N

assay

≥98% (HPLC)

storage condition

desiccated

color

white to off-white

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

Quality Level

100

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

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.

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000451812
0000451812
0000451815
0000182122
0000182122

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A review of the use of adapalene for the treatment of acne vulgaris
Piskin S and Uzunali E
Therapeutics and Clinical Risk Management, 3(4), 621-621 (2007)
Benzimidazoles promote anti-TNF mediated induction of regulatory macrophages and enhance therapeutic efficacy in a murine model
Wildenberg M E, et al.
Journal of Crohn's & Colitis, 11(12) (2017)
The retinoic acid receptor (RAR) $\alpha$-specific agonist Am80 (tamibarotene) and other RAR agonists potently inhibit hepatitis B virus transcription from cccDNA
Nkongolo S, et al.
Antiviral Research, 168(4) (2019)
Nobukazu Hayashi et al.
The Journal of dermatology, 39(6), 511-515 (2011-12-16)
We conducted a randomized controlled trial in patients with acne vulgaris with moderate to severe inflammatory lesions. The patients were assigned to the following three treatment groups: group A received monotherapy with 0.1% topical adapalene gel for 4 weeks; group
Suleyman Piskin et al.
Therapeutics and clinical risk management, 3(4), 621-624 (2008-05-14)
Acne is a disease of the pilosebaceous unit with involving abnormalities in sebum production, microbial flora changes, abnormal keratinization, and inflammation. There are several therapeutic options like topical and systemic retinoids, antibiotics, and systemic hormonal drugs. The topical retinoids a
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