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1353500

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
NACRES:
NA.24
PubChem Substance ID:
329750208
UNSPSC Code:
41116107
MDL number:
MFCD00079542
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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.

signalword

Danger

target_organs

Respiratory system

Storage Class

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

flash_point_f

Not applicable

flash_point_c

Not applicable

Hazard Classifications

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

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Isotretinoin
United States Pharmacopeia, 2457-2457 (2020)
Tretinoin
United States Pharmacopeia, 41(4), 4478-4478 (2020)
Isotretinoin Capsules
United States Pharmacopeia, 48(4), 2458-2458 (2023)
F L Meyskens et al.
Critical reviews in oncology/hematology, 3(1), 75-101 (1985-01-01)
Retinoids, particularly 13-cis-retinoic acid, have shown great promise against a number of benign, but serious dermatological conditions. In animal models, 13-cis-retinoic acid functions is a potent antipromoter whether a cancer has been initiated by chemical, physical, or viral agents. Additionally
Fatma Cetinözman et al.
The Journal of dermatological treatment, 25(2), 119-122 (2012-11-21)
Androgens appear to play a role in the development of acne, and presence of acne is a potential marker of hyperandrogenism. The authors evaluated androgens and insulin sensitivity markers before and after treatment with isotretinoin in women with post-adolescent severe
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Global Trade Item Number

SKUGTIN
1353500-200MG04061838730633

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