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1353500

USP

Isotretinoin

United States Pharmacopeia (USP) Reference Standard

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Synonym(s):
13-cis-Retinoic acid, 13-cis-Vitamin A acid, Isotretinoin
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
Molecular Weight:
300.44
MDL number:
PubChem Substance ID:

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

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This Item
I0800000PHR11881674004
Isotretinoin United States Pharmacopeia (USP) Reference Standard

1353500

Isotretinoin

Isotretinoin European Pharmacopoeia (EP) Reference Standard

I0800000

Isotretinoin

Isotretinoin Pharmaceutical Secondary Standard; Certified Reference Material

PHR1188

Isotretinoin

Tretinoin United States Pharmacopeia (USP) Reference Standard

1674004

Tretinoin

manufacturer/tradename

USP

manufacturer/tradename

EDQM

manufacturer/tradename

-

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

format

neat

format

neat

format

neat

format

neat

API family

isotretinoin

API family

isotretinoin

API family

isotretinoin

API family

tretinoin

mp

172-175 °C (lit.)

mp

172-175 °C (lit.)

mp

172-175 °C (lit.)

mp

180-181 °C (lit.)

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 for use in specified quality tests and assays.

Also used to prepare standard, standard stock, system suitability, system suitability stock solution for assay, and impurity analysis in Phenoxyethanol according to United States Pharmacopeia (USP) monograph:
  • Isotretinoin Capsules
  • Tretinoin
  • Isotretinoin

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.

related product

Product No.
Description
Pricing

pictograms

Exclamation markHealth hazard

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Isotretinoin Capsules
United States Pharmacopeia, 48(4), 2458-2458 (2023)
Tretinoin
United States Pharmacopeia, 41(4), 4478-4478 (2020)
Isotretinoin
United States Pharmacopeia, 2457-2457 (2020)
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.
Antoine Racine et al.
The American journal of gastroenterology, 109(4), 563-569 (2014-02-19)
Isotretinoin, a drug widely prescribed for severe acne, has been suspected to increase the risk of ulcerative colitis (UC), but data are conflicting. To further examine the association between isotretinoin use and risk for UC and Crohn's disease (CD), we

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