1353500

USP

Isotretinoin

United States Pharmacopeia (USP) Reference Standard

Synonym(s):
Isotretinoin, 13-cis-Retinoic acid
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
Molecular Weight:
300.44
MDL number:
PubChem Substance ID:

grade

pharmaceutical primary standard

form

neat

manufacturer/tradename

USP

mp

172-175 °C (lit.)

Featured Industry

Pharmaceutical (small molecule)

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

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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.

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

USP issued SDS can be found here.
Sales restrictions may apply.

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

hazcat

Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

storage_class_code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Dimitris Rigopoulos et al.
Clinics in dermatology, 28(1), 24-30 (2010-01-20)
Acne is one of the most prevalent diseases in dermatology: Millions of people worldwide experience this distressing condition. To determine the appropriate therapeutic strategy, there is a strong need for a standardized classification system of acne. The exact molecular mechanism...
Kabir Sardana et al.
Indian journal of dermatology, venereology and leprology, 76(1), 7-13 (2010-01-12)
Low-dose isotretinoin (0.5 mg/kg/day) is a mode of therapy for mild to moderate grades of acne. We analyzed the various trials of this mode of therapy with or without combination with topical agents. We also statistically analyzed the results, efficacy...
W S Blaner
Journal of the American Academy of Dermatology, 45(5), S129-S135 (2001-10-19)
Retinoids (vitamin A and its derivatives) are potent substances for regulating the expression of many different genes within the body. The gene regulatory activities of retinoids are mediated primarily by the all-trans and 9-cis isomers of retinoic acid. Although 13-cis-retinoic...
Antoine Racine et al.
The American journal of gastroenterology, 109(4), 563-569 (2014-02-19)
Isotretinoin, a drug widely prescribed for severe acne, has been suspected to increase the risk of ulcerative colitis (UC), but data are conflicting. To further examine the association between isotretinoin use and risk for UC and Crohn's disease (CD), we...
E A Eisenhauer et al.
Leukemia, 8(10), 1622-1625 (1994-10-01)
Preclinical data indicate that the combination of retinoids and interferons have synergistic antiproliferative and differentiating effects in some hematologic and solid tumor models. These observations have led to clinical trials in which 13-cis-retinoic acid (13cRA) 1 mg/kg/day was combined with...

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