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Merck

PHR1388

Adapalene

Pharmaceutical Secondary Standard; Certified Reference Material

Sinónimos:

Adapalene, 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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Fórmula empírica (notación de Hill):
C28H28O3
Número CAS:
106685-40-9
Peso molecular:
412.52
NACRES:
NA.24
PubChem Substance ID:
329823363
UNSPSC Code:
41116107
MDL number:
MFCD03106112

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Nombre del producto

Adapalene, Pharmaceutical Secondary Standard; Certified Reference Material

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-

SMILES string

COc1ccc(cc1C23C[C@H]4C[C@H](C[C@H](C4)C2)C3)-c5ccc6cc(ccc6c5)C(O)=O

InChI key

LZCDAPDGXCYOEH-AADAIPAGSA-N

grade

certified reference material
pharmaceutical secondary standard

agency

traceable to Ph. Eur. Y0001121
traceable to USP 1011709

API family

adapalene

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-30°C

Quality Level

300

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Analysis Note

These secondary standards offer multi-traceability to the USP and EP (PhEur) primary standards, where they are available.

Application

Adapalene may be used as a pharmaceutical reference standard for the quantification of the analyte in topical gel formulations using high-performance liquid chromatography technique.
These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

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).
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.

General description

Adapalene is a third-generation synthetic retinoid and a highly lipophilic compound derived from naphthoic acid. It is widely used in the treatment of acne.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.
To see an example of a Certificate of Analysis for this material enter LRAC3530 in the slot below. This is an example certificate only and may not be the lot that you receive.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361d

Hazard Classifications

Repr. 2

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Novel stability-indicating RP-HPLC method for the simultaneous estimation of clindamycin phosphate and adapalene along with preservatives in topical gel formulations
Modi.BP and Shah.JN
Scientia Pharmaceutica, 82(4), 799-814 (2014)
A simple HPLC-DAD method for determination of adapalene in topical gel formulation
Martins AL, et al.
Journal of Chromatographic Science, 49(10), 796-800 (2011)
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
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