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USP

Isotretinoin

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
4759-48-2
Molecular Weight:
300.44
MDL number:
MFCD00079542
UNSPSC Code:
41116107
PubChem Substance ID:
329750208
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

isotretinoin

manufacturer/tradename

USP

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.

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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H319,H335,H360FD

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘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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