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1011709

USP

Adapalene

United States Pharmacopeia (USP) Reference Standard

Synonyme(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

Formule empirique (notation de Hill):
C28H28O3
Numéro CAS:
106685-40-9
Poids moléculaire :
412.52
Numéro MDL:
MFCD03106112
Code UNSPSC :
41116107
ID de substance PubChem :
329748898
Nomenclature NACRES :
NA.24

Qualité

pharmaceutical primary standard

Famille d'API

adapalene

Fabricant/nom de marque

USP

Application(s)

pharmaceutical (small molecule)

Format

neat

Chaîne SMILES 

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-

Clé InChI

LZCDAPDGXCYOEH-AADAIPAGSA-N

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Description générale

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

Actions biochimiques/physiologiques

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.

Remarque sur l'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.  ​

Autres remarques

Sales restrictions may apply.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

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

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Warning

Mentions de danger

H361d

Classification des risques

Repr. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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 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
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
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
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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