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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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Product Name

Acitretin, United States Pharmacopeia (USP) Reference Standard

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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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.  ​

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).

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.

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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M Lebwohl et al.
Journal of the American Academy of Dermatology, 45(4), 544-553 (2001-09-25)
Although adjunctive treatment with retinoids in concert with either psoralen-ultraviolet A (PUVA) or ultraviolet B (UVB) phototherapy has been a treatment option for chronic, moderate to severe plaque psoriasis for nearly two decades, acitretin-UV therapy is an underutilized therapeutic modality.
British Association of Dermatologists guidelines on the efficacy and use of acitretin in dermatology.
A D Ormerod et al.
The British journal of dermatology, 162(5), 952-963 (2010-04-29)
Alessandro Borghi et al.
Acta dermato-venereologica, 95(3), 332-336 (2014-07-01)
The efficacy and safety of acitretin was evaluated retrospectively in a cohort of 46 patients with moderate to severe plaque psoriasis (Psoriasis Area and Severity Index (PASI) range 10-42). Patients were treated at an initial dose of 10 mg/day acitretin
Agranulocytosis and total scalp alopecia following acitretin.
T A Chave et al.
The British journal of dermatology, 148(5), 1063-1064 (2003-06-06)
Chai Sue Lee et al.
Expert opinion on pharmacotherapy, 6(10), 1725-1734 (2005-08-10)
Acitretin is a second-generation, systemic retinoid that has been approved for the treatment of psoriasis since 1997. It can be considered one of the treatments of choice for pustular and erythrodermic psoriasis. However, the efficacy of acitretin as a monotherapy
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