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1353500

USP

Isotretinoin

United States Pharmacopeia (USP) Reference Standard

Synonyme(s) :

13-cis-Retinoic acid, 13-cis-Vitamin A acid, Isotretinoin

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About This Item

Formule empirique (notation de Hill):
C20H28O2
Numéro CAS:
4759-48-2
Poids moléculaire :
300.44
Numéro MDL:
MFCD00079542
Code UNSPSC :
41116107
ID de substance PubChem :
329750208
Nomenclature NACRES :
NA.24

Qualité

pharmaceutical primary standard

Famille d'API

isotretinoin

Fabricant/nom de marque

USP

Pf

172-175 °C (lit.)

Application(s)

pharmaceutical (small molecule)

Format

neat

Chaîne SMILES 

[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-

Clé InChI

SHGAZHPCJJPHSC-XFYACQKRSA-N

Informations sur le gène

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

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Description générale

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

Actions biochimiques/physiologiques

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.

Remarque sur l'analyse

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.  ​

Autres remarques

Sales restrictions may apply.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H315,H319,H335,H360FD

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Isotretinoin
United States Pharmacopeia, 2457-2457 (2020)
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
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
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.
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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