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Y0001121

Adapalene

Name: Adapalene
Brand: SIAL

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

6-(4-Methoxy-3-tricyclo[3.3.1.1^3,7]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

MDL number:

MFCD03106112

UNSPSC Code:

41116107

PubChem Substance ID:

329831273

NACRES:

NA.24

grade

pharmaceutical primary standard

API family

adapalene

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

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-

InChI key

LZCDAPDGXCYOEH-AADAIPAGSA-N

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Analytical Reference Standards

Pharmacopeia & Metrological Institute Standards

General description

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.

Application

Adapalene EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

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.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

related product

Product No.

Description

Pricing

1011710

1011709

Adapalene, United States Pharmacopeia (USP) Reference Standard

1011721

1011732

1011743

1011754

PHR2827

PHR2828

PHR2829

PHR2830

Pictograms

GHS08

Signal Word

Warning

Hazard Statements

H361d

Precautionary Statements

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Repr. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Spotlight on adapalene in acne vulgaris.

John Waugh et al.

American journal of clinical dermatology, 5(5), 369-371 (2004-11-24)

Adapalene (Differin) is a retinoid agent indicated for the topical treatment of acne vulgaris. In clinical trials, 0.1% adapalene gel has proved to be effective in this indication and was as effective as 0.025% tretinoin gel, 0.1% tretinoin microsphere gel

Adapalene for the treatment of acne vulgaris.

J S Weiss et al.

Journal of the American Academy of Dermatology, 39(2 Pt 3), S50-S54 (1998-08-14)

An update of recent clinical trials examining adapalene and acne.

J E Wolf

Journal of the European Academy of Dermatology and Venereology : JEADV, 15 Suppl 3, 23-29 (2002-02-15)

Topical retinoids are a mainstay in the treatment of acne vulgaris. In the past these agents have been associated with irritant effects, however, newer generations of topical retinoids have emerged that have been designed to be less irritating. This paper

Pharmacology and chemistry of adapalene.

B Shroot et al.

Journal of the American Academy of Dermatology, 36(6 Pt 2), S96-103 (1997-06-01)

Retinoid research in the field of dermatology has been influenced by the clinical success of topical tretinoin and oral isotretinoin in the treatment of acne, and by the discovery of high-affinity binding proteins for retinoic acid mediating its action and

Effective treatment of localized Darier's disease with adapalene 0.1% gel.

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.

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