I0800000

Isotretinoin

European Pharmacopoeia (EP) Reference Standard

• Synonyme(s) : 13-cis-Retinoic acid, Isotretinoin
• Formule empirique (notation de Hill): C₂₀H₂₈O₂
• Numéro CAS: 4759-48-2
• Poids moléculaire : 300.44
• Numéro MDL: MFCD00079542
• Code UNSPSC : 41116107
• ID de substance PubChem : 329815327
• Nomenclature NACRES : NA.24

Propriétés

• Source biologique: synthetic
• Qualité: pharmaceutical primary standard
• Agence: EP
• Famille d'API: isotretinoin
• Forme: solid
• Fabricant/nom de marque: EDQM
• Technique(s): gas chromatography (GC): suitable; liquid chromatography (LC): suitable
• Pf: 172-175 °C (lit.)
• Application(s): pharmaceutical (small molecule)
• Format: neat
• Chaîne SMILES: [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-
• Clé InChI: SHGAZHPCJJPHSC-XFYACQKRSA-N
• Informations sur le gène: human ... RARA(5914) , RARB(5915) , RARG(5916)

Description

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.
Isotretinoin, a vital isomer of vitamin A, is implicated in the treatment of severe recalcitrant nodular acne disorder. It is the only drug known to operate against the major pathogenic factors of acne. It serves to diminish the sebaceous gland activity, thereby resulting in the correction of keratinization defect.

Application

Isotretinoin may be used as an EP reference standard for the determination of the analyte in pharmaceutical formulations by various chromatography techniques.

Actions biochimiques/physiologiques

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.

Conditionnement

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Autres remarques

Sales restrictions may apply.

Informations sur la sécurité

• Pictogrammes: GHS08,GHS07
• Mention d'avertissement: Danger
• Mentions de danger: H315,H319,H335,H360FD
• Conseils de prudence: P202 - P261 - P264 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Classification des risques: Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Organes cibles: Respiratory system
• Code de la classe de stockage: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable