1353500

Isotretinoin

United States Pharmacopeia (USP) Reference Standard

• Synonym(s): 13-cis-Retinoic acid, 13-cis-Vitamin A acid, Isotretinoin
• Empirical Formula (Hill Notation): C₂₀H₂₈O₂
• CAS Number: 4759-48-2
• Molecular Weight: 300.44
• NACRES: NA.24
• PubChem Substance ID: 329750208
• UNSPSC Code: 41116107
• MDL number: MFCD00079542

Properties

• grade: pharmaceutical primary standard
• agency: USP
• API family: isotretinoin
• manufacturer/tradename: USP
• mp: 172-175 °C (lit.)
• application(s): pharmaceutical (small molecule); pharmaceutical
• format: neat
• 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

Find answers to frequently asked questions on USP products in USP FAQs.

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.

Application

Isotretinoin USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:

• Isotretinoin Capsules
• Tretinoin

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 products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

Safety Information

• Pictograms: GHS08,GHS07,GHS09
• Signal Word: Danger
• Hazard Codes: H315,H319,H335,H360D,H410
• Precautionary Statements: P202 - P261 - P273 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Target Organs: Respiratory system
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• Hazard Classifications: Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3