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1011709

USP

Adapalene

United States Pharmacopeia (USP) Reference Standard

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:
Molecular Weight:
412.52
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

adapalene

manufacturer/tradename

USP

application(s)

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-

InChI key

LZCDAPDGXCYOEH-AADAIPAGSA-N

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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 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 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.

Analysis Note

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.  ​

Other Notes

Sales restrictions may apply.

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Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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.
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)

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