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1011709

USP

Adapalene

United States Pharmacopeia (USP) Reference Standard

Sinônimo(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

Fórmula empírica (Notação de Hill):
C28H28O3
Número CAS:
106685-40-9
Peso molecular:
412.52
Número MDL:
MFCD03106112
Código UNSPSC:
41116107
ID de substância PubChem:
329748898
NACRES:
NA.24

grau

pharmaceutical primary standard

família API

adapalene

fabricante/nome comercial

USP

aplicação(ões)

pharmaceutical (small molecule)

Formato

neat

cadeia de caracteres 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-

chave InChI

LZCDAPDGXCYOEH-AADAIPAGSA-N

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Descrição geral

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.

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Nota de análise

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.  ​

Outras notas

Sales restrictions may apply.

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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

Pictogramas

Health hazard
GHS08

Palavra indicadora

Warning

Frases de perigo

H361d

Classificações de perigo

Repr. 2

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number

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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.
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
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
L E Millikan
International journal of dermatology, 39(10), 784-788 (2000-11-30)
Extensive modification of the retinoic acid molecular skeleton has resulted in the development of adapalene, a more stable, less irritating compound with receptor selectivity. Adapalene selectively targets nuclear retinoic acid receptors found primarily in the epidermis. Pharmacologic and preclinical studies
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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