PHR1188

Isotretinoin

Pharmaceutical Secondary Standard; Certified Reference Material

• Synonym(s): 13-cis-Retinoic acid, Isotretinoin
• Empirical Formula (Hill Notation): C₂₀H₂₈O₂
• CAS Number: 4759-48-2
• Molecular Weight: 300.44
• EC Number: 225-296-0
• MDL number: MFCD00079542
• PubChem Substance ID: 329823198
• NACRES: NA.24

Properties

• grade: certified reference material; pharmaceutical secondary standard
• Quality Level: 300
• Agency: traceable to Ph. Eur. I0800000; traceable to USP 1353500
• CofA: current certificate can be downloaded
• technique(s): HPLC: suitable; gas chromatography (GC): suitable
• mp: 172-175 °C (lit.)
• application(s): pharmaceutical (small molecule)
• format: neat
• storage temp.: -10 to -25°C
• SMILES string: [H]\C(C(O)=O)=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C
• InChI: 1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-
• InChI key: SHGAZHPCJJPHSC-XFYACQKRSA-N
• Gene Information: human ... RARA(5914) , RARB(5915) , RARG(5916)

Description

General description

Isotretinoin is a vitamin A derivative, obtained from the isomerization of retinoic acid in the body. It is therapeutically used to treat severe recalcitrant nodular acne.[1] It is also reported to exhibit anti-inflammatory and anti-tumor activities.
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

Isotretinoin may be used as a pharmaceutical reference standard for the quantification of the analyte in pharmaceutical formulations using reversed-phase high-performance liquid chromatography.[1]

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

13-cis-Retinoic acid (RA) has anti-inflammatory and anti-tumor action. The action of RA is mediated through RAR-β and RAR-α receptors. RA attenuates iNOS expression and activity in cytokine-stimulated murine mesangial cells. It induces mitochondrial membrane permeability transition, observed as swelling and as a decrease in membrane potential, and stimulates the release of cytochrome c implicating mechanisms through the apoptosis pathway. These activities are reversed by EGTA and cyclosporin A. RA also increases MMP-1 protein expression partially via increased transcription.

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 LRAC0144 in the slot below. This is an example certificate only and may not be the lot that you receive.

Safety Information

• Pictograms: GHS07,GHS08
• Signal Word: Danger
• Hazard Statements: H315 - H319 - H335 - H360FD
• Precautionary Statements: P202 - P261 - P264 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable