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A7486

Sigma-Aldrich

Adapalen

≥98% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C28H28O3
CAS-Nummer:
106685-40-9
Molekulargewicht:
412.52
MDL-Nummer:
MFCD03106112
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329770932
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Lagerbedingungen

desiccated

Farbe

white to off-white

Löslichkeit

DMSO: >10 mg/mL

Lagertemp.

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-

InChIKey

LZCDAPDGXCYOEH-AADAIPAGSA-N

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Anwendung

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. Wirkung

Retinsäure-Analogon, das ein RARβ- und RARγ-Agonist ist (AC50-Werte betragen 2.2, 9.3, 22 und > 1000 nM für RARβ-, RARγ-, RARα- bzw. RXRα-Rezeptoren). Hemmt in vitro die Proliferation und induziert Apoptose in kolorektalen Krebszellen. Zeigt komedolytische Wirkung. Durch seine einzigartigen pharmakologischen Eigenschaften ist es besser als andere Retinoide zur Behandlung von Akne geeignet.
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.

Leistungsmerkmale und Vorteile

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.

Piktogramme

Health hazard
GHS08

Signalwort

Warning

H-Sätze

H361d

Gefahreneinstufungen

Repr. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
051M4749V
020M47133
020M47132
020M46131
020M4713

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Tazarotene ≥98% (HPLC)

Sigma-Aldrich

T7080

Tazarotene

Acitretin ≥98.0% (HPLC)

Sigma-Aldrich

44707

Acitretin

Probenecid

Sigma-Aldrich

P8761

Probenecid

Luperox® A75, Benzoylperoxid 75%, remainder water

Sigma-Aldrich

517909

Luperox® A75, Benzoylperoxid

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
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
R N Brogden et al.
Drugs, 53(3), 511-519 (1997-03-01)
Adapalene, a naphthoic acid derivative with retinoid-like activity, is used for the topical treatment of mild to moderate acne vulgaris. It binds to retinoic acid receptors found predominantly in the terminal differentiation zone of epidermis and is more active than
L E Millikan
Journal of the European Academy of Dermatology and Venereology : JEADV, 15 Suppl 3, 19-22 (2002-02-15)
Adapalene, a naphthoic-acid derivative, possesses some of the biological activities of tretinoin but has distinct physicochemical properties and binding properties for selective affinity for retinoic acid receptors. As such, adapalene is less likely to be associated with certain local tolerability
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