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

Target Organs

Respiratory system

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Stephen E Wolverton et al.
American journal of clinical dermatology, 14(2), 71-76 (2013-04-06)
Isotretinoin is a remarkably effective drug for severe, recalcitrant acne vulgaris. Soon after the drug's release in the early 1980s, a number of important adverse effects were reported subsequently leading to a variety of medical and medicolegal controversies. Three of...
Jane L Armstrong et al.
Biochemical pharmacology, 69(9), 1299-1306 (2005-04-14)
Retinoic acid isomers have been used with some success as chemotherapeutic agents, most recently with 13-cis retinoic acid showing impressive clinical efficacy in the paediatric malignancy neuroblastoma. The aim of this commentary is to review the evidence that 13-cis retinoic...
Elie B Lowenstein et al.
Clinics in dermatology, 29(6), 652-661 (2011-10-22)
Isotretinoin has revolutionized the field of dermatology, offering a cure for severe acne vulgaris and a therapeutic option for a variety of other chronic diseases and cancers. This drug has done more for many diseases in medicine than many drug...
James Q Del Rosso
Journal of drugs in dermatology : JDD, 12(6), 626-631 (2013-07-11)
Oral isotretinoin is a non-aromatic oral retinoid that is highly effective for the treatment of severe inflammatory acne vulgaris that is refractory and/or prone to scarring, and has also been used successfully to treat several other disorders in selected cases....
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...

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