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Merck
CN

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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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-

SMILES string

[H]\C(C(O)=O)=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C

InChI key

SHGAZHPCJJPHSC-XFYACQKRSA-N

grade

pharmaceutical primary standard

API family

isotretinoin

manufacturer/tradename

USP

mp

172-175 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

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)
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.
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
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