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Merck
CN

1011007

USP

Acitretin

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

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About This Item

Empirical Formula (Hill Notation):
C21H26O3
CAS Number:
55079-83-9
Molecular Weight:
326.43
NACRES:
NA.24
PubChem Substance ID:
329748897
UNSPSC Code:
41116107
MDL number:
MFCD00866632

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InChI key

IHUNBGSDBOWDMA-AQFIFDHZSA-N

SMILES string

COc1cc(C)c(\C=C\C(C)=C\C=C\C(C)=C\C(O)=O)c(C)c1C

InChI

1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+

grade

pharmaceutical primary standard

API family

acitretin

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

Gene Information

human ... RARA(5914), RARB(5915), RARG(5916), RXRA(6256), RXRB(6257), RXRG(6258)

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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

Acitretin 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:
  • Acitretin Capsules

Biochem/physiol Actions

Synthetic retinoid that is a metabolite of etretinate. Preferentially binds to cellular retinoic acid binding proteins (CRABPs).

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

Hazard Classifications

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

Storage Class

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

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Jennifer Hayes et al.
Journal of drugs in dermatology : JDD, 10(4), 409-412 (2011-04-02)
The potential relationship between systemic retinoids used in dermatology and affective disorders is controversial. Acitretin, which is widely used in the treatment of psoriasis is part of this controversy secondary to its chemical relation to isotretinoin, a drug which has
John Starling et al.
Journal of drugs in dermatology : JDD, 4(6), 690-696 (2005-11-24)
Oral retinoids are among the first line agents for treatment of pustular and erythrodermic psoriasis, and they are effective in combination with phototherapy and other topical and systemic agents for the treatment of plaque psoriasis. Acitretin is the leading oral
G Carretero et al.
Actas dermo-sifiliograficas, 104(7), 598-616 (2013-07-31)
Phototherapy, classic systemic treatments (methotrexate, acitretin, and ciclosporin), and biologic agents (etanercept, infliximab, adalimumab, and ustekinumab) constitute a broad therapeutic arsenal that increases the likelihood of achieving control of severe and extensive disease in patients with psoriasis. Acitretin continues to
M M Tang et al.
Dermatology (Basel, Switzerland), 225(4), 338-343 (2013-01-25)
Generalized pustular psoriasis (GPP) is a severe inflammatory disease characterized by recurrent eruptions of sterile pustules on erythematous skin. Although tumor necrosis factor (TNF) antagonists may lead to a rapid resolution of GPP, the mechanism of action of these agents
Mariëlle Te Booij et al.
The Journal of dermatological treatment, 22(2), 86-89 (2010-08-03)
Acitretin is a time-honored treatment for psoriasis. During the last decade biologics have revolutionized the treatment of psoriasis. This raises the question: What is the position of acitretin as a classical systemic treatment for psoriasis in the era of biologics?
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