PHR1388

Adapalene

Pharmaceutical Secondary Standard; Certified Reference Material

• Synonym(s): Adapalene, 6-(4-Methoxy-3-tricyclo[3.3.1.1^3,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid, 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid, CD-271, Differin
• Empirical Formula (Hill Notation): C₂₈H₂₈O₃
• CAS Number: 106685-40-9
• Molecular Weight: 412.52
• MDL number: MFCD03106112
• UNSPSC Code: 41116107
• PubChem Substance ID: 329823363
• NACRES: NA.24

Properties

• grade: certified reference material; pharmaceutical secondary standard
• Quality Level: 300
• 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
• 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

Description

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.

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

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.

Footnote

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.

Safety Information

• pictograms: GHS08
• signalword: Warning
• hcodes: H361d
• pcodes: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Repr. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable