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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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M Lebwohl et al.
The Journal of dermatological treatment, 14 Suppl 2, 3-6 (2003-10-28)
Retinoids have been used for the treatment and suppression of cutaneous malignancies in patients with basal cell nevus syndrome, xeroderma pigmentosum, and in patients with recurrent skin cancers as a result of immunosuppression for renal transplantation. We report a 40-year-old
Mei-Lin Pang et al.
Expert opinion on drug metabolism & toxicology, 4(7), 953-964 (2008-07-16)
Acitretin is a systemic retinoid used for psoriasis. It normalizes cellular differentiation and maturation and is also used as a chemopreventive agent against cutaneous malignancies. However, it is not used frequently because of its side-effect profile. Safety and efficacy of
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?
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
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
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