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Isotretinoin

European Pharmacopoeia (EP) Reference Standard

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Synonym(s):
13-cis-Retinoic acid, Isotretinoin
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
4759-48-2
Molecular Weight:
300.44
MDL number:
MFCD00079542
PubChem Substance ID:
329815327
NACRES:
NA.24

biological source

synthetic

grade

pharmaceutical primary standard

Agency

EP

API family

isotretinoin

form

solid

manufacturer/tradename

EDQM

technique(s)

gas chromatography (GC): suitable
liquid chromatography (LC): suitable

mp

172-175 °C (lit.)

application(s)

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

human ... RARA(5914) , RARB(5915) , RARG(5916)

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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.
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.

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.

Packaging

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

Other Notes

Sales restrictions may apply.

related product

Product No.
Description
Pricing

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Isotretinoin
European Pharmacopoeia Commission and European Directorate for the Quality of Medicines & Healthcare
European pharmacopoeia, 3(5), 5705-5706 (2018)
Determination of isotretinoin in pharmaceutical formulations by reversed-phase HPLC
Guimar?es CA, et al.
Journal of Biomedical Science and Engineering, 3(5), 454-458 (2010)
Development of a gas chromatography method for the determination of isotretinoin and its degradation products in pharmaceuticals
Lima EM, et al.
Journal of Pharmaceutical and Biomedical Analysis, 38(4), 678-685 (2005)
Kaisar Raza et al.
Colloids and surfaces. B, Biointerfaces, 105, 67-74 (2013-01-30)
Isotretinoin (ITR) is a drug of choice in the treatment of all types of acne, including recalcitrant, severe and nodulocystic. The most widely employed route of its administration, i.e., oral intake, is reported to be associated with severe side-effects including
Emily Yiping Gan et al.
The Journal of dermatological treatment, 24(5), 387-391 (2012-03-07)
Oral isotretinoin is effective for acne vulgaris but concerns remain regarding its adverse effects. This study aims to evaluate the safety and efficacy of isotretinoin for acne vulgaris in Asian patients. We conducted a 4-year retrospective study on all patients
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