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1011709

USP

Adapalen

United States Pharmacopeia (USP) Reference Standard

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:
41116107
PubChem Substanz-ID:
329748898
NACRES:
NA.24

Qualität

pharmaceutical primary standard

API-Familie

adapalene

Hersteller/Markenname

USP

Anwendung(en)

pharmaceutical (small molecule)

Format

neat

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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Allgemeine Beschreibung

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Anwendung

Adapalene USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Adapalene Gel

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.

Hinweis zur Analyse

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Sonstige Hinweise

Sales restrictions may apply.

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

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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J C English et al.
Cutis, 63(4), 227-230 (1999-05-06)
Darier's disease is an autosomal dominant disorder of keratinization that can produce unique clinical manifestations. Oral and topical retinoid products have been the mainstay therapy for this population, but local as well as systemic side effects often limit their effectiveness.
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
L E Millikan
International journal of dermatology, 39(10), 784-788 (2000-11-30)
Extensive modification of the retinoic acid molecular skeleton has resulted in the development of adapalene, a more stable, less irritating compound with receptor selectivity. Adapalene selectively targets nuclear retinoic acid receptors found primarily in the epidermis. Pharmacologic and preclinical studies
Cynthia E Irby et al.
The Journal of adolescent health : official publication of the Society for Adolescent Medicine, 43(5), 421-424 (2008-10-14)
Topical retinoids help address the early lesions of acne vulgaris. Consensus guidelines advocate the use of topical retinoids as the primary treatment for most forms of acne vulgaris. However, all topical retinoid preparations may be irritating, and this may contribute
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