Isotretinoin
SIAL/I0800000 - European Pharmacopoeia (EP) Reference Standard
Synonym: 13-cis-Retinoic acid; Isotretinoin
CAS Number: 4759-48-2
Empirical Formula (Hill Notation): C20H28O2
Molecular Weight: 300.44
MDL Number: MFCD00079542
Linear Formula: C20H28O2
Product Type: Chemical
| agency | EP |
| API family | isotretinoin |
| application(s) | pharmaceutical (small molecule) |
| biological source | synthetic |
| form | solid |
| format | neat |
| grade | pharmaceutical primary standard |
| InChI | 1S/C20H28O2/c1-15(8-6-9-1 |
| InChI key | SHGAZHPCJJPHSC-XFYACQKRSA |
| manufacturer/tradename | EDQM |
| mp | 172-175 °C (lit.) |
| SMILES string | [H]C(C(O)=O)=C(C)C=CC= |
| technique(s) | gas chromatography (GC): suitable |
| liquid chromatography (LC): suitable |
| Application: | Isotretinoin may be used as an EP reference standard for the determination of the analyte in pharmaceutical formulations by various chromatography techniques. |
| 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. |
| General description: | 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. |
| Other Notes: | Sales restrictions may apply. |
| Packaging: | The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue . |
| Symbol |   GHS07,GHS08 |
| Signal word | Danger |
| Hazard statements | H315 - H319 - H335 - H360 |
| Precautionary statements | P201 - P302 + P352 - P305 + P351 + P338 - P308 + P313 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| mp | 172-175 °C (lit.) |
| UNSPSC | 41116107 |