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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
MDL number:
MFCD00866632
UNSPSC Code:
41116107
PubChem Substance ID:
329748897
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

acitretin

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

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+

InChI key

IHUNBGSDBOWDMA-AQFIFDHZSA-N

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.

Signal Word

Danger

Hazard Statements

H315,H319,H360,H410

Hazard Classifications

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

Storage Class Code

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Agranulocytosis and total scalp alopecia following acitretin.
T A Chave et al.
The British journal of dermatology, 148(5), 1063-1064 (2003-06-06)
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)
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
Chai Sue Lee et al.
Expert opinion on drug safety, 8(6), 769-779 (2009-12-10)
Acitretin is an oral retinoid that is approved for the treatment of psoriasis. It is unique compared to other systemic therapies for psoriasis such as methotrexate and cyclosporine in that it is not immunosuppressive. It is, therefore, safe for use
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