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A7486

Sigma-Aldrich

Adapalene

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C28H28O3
Numéro CAS:
106685-40-9
Poids moléculaire :
412.52
Numéro MDL:
MFCD03106112
Code UNSPSC :
12352200
ID de substance PubChem :
329770932
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to off-white

Solubilité

DMSO: >10 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

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-

Clé InChI

LZCDAPDGXCYOEH-AADAIPAGSA-N

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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.

Actions biochimiques/physiologiques

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). 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.

Caractéristiques et avantages

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.

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Warning

Mentions de danger

H361d

Classification des risques

Repr. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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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
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)
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
Manon E Wildenberg et al.
Journal of Crohn's & colitis, 11(12), 1480-1490 (2017-09-30)
Regulatory macrophages play a critical role in tissue repair, and we have previously shown that anti-tumour necrosis factor [TNF] antibodies induce these macrophages in vitro and in vivo in IBD patients. The induction of regulatory macrophages can be potentiated using
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)
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