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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:
106685-40-9
Molecular Weight:
412.52
MDL number:
MFCD03106112
UNSPSC Code:
41116107
PubChem Substance ID:
329748898
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.

related product

Product No.
Description
Pricing

1011710

Adapalene Related Compound A, United States Pharmacopeia (USP) Reference Standard

1011721

Adapalene Related Compound B, United States Pharmacopeia (USP) Reference Standard

1011732

Adapalene Related Compound C, United States Pharmacopeia (USP) Reference Standard

1011743

Adapalene Related Compound D, United States Pharmacopeia (USP) Reference Standard

1011754

Adapalene Related Compound E, United States Pharmacopeia (USP) Reference Standard

Y0001121

Adapalene, European Pharmacopoeia (EP) Reference Standard

Y0001120

Adapalene impurity C, European Pharmacopoeia (EP) Reference Standard

Y0001119

Adapalene for peak identification, European Pharmacopoeia (EP) Reference Standard

BP1120

Adapalene, British Pharmacopoeia (BP) Reference Standard

BP1121

Adapalene impurity standard, British Pharmacopoeia (BP) Reference Standard

PHR2827

Adapalene Related Compound A, certified reference material, pharmaceutical secondary standard

PHR2828

Adapalene Related Compound B, certified reference material, pharmaceutical secondary standard

PHR2829

Adapalene Related Compound C, Pharmaceutical Secondary Standard; Certified Reference Material

PHR2830

Adapalene Related Compound D, certified reference material, pharmaceutical secondary standard

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d

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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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
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
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
View All Related Papers

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