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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

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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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This Item
BP1120PHR1388Y0001119
Adapalene British Pharmacopoeia (BP) Reference Standard

BP1120

Adapalene

manufacturer/tradename

USP

manufacturer/tradename

BP

manufacturer/tradename

-

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical
pharmaceutical small molecule

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

format

neat

format

neat

format

neat

format

neat

API family

adapalene

API family

adapalene

API family

adapalene

API family

adapalene

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


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    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)
    J Czernielewski et al.
    Journal of the European Academy of Dermatology and Venereology : JEADV, 15 Suppl 3, 5-12 (2002-02-15)
    The emergence of oral and topical retinoids was a major advance in the clinical management of acne vulgaris. However, the benefits of these agents were somewhat limited by the degree of side effects caused by these drugs. Over the last
    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
    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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