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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

Key Documents

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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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Rashmi Sarkar et al.
Indian journal of dermatology, venereology and leprology, 79(6), 759-771 (2013-11-02)
Acitretin, a synthetic retinoid has gradually replaced etretinate in today's dermatologic practice because of its more favorable pharmacokinetics. Acitretin over the past 20 years has proven useful in a number of difficult-to-treat hyperkeratotic and inflammatory dermatoses and nonmelanoma skin cancers.
Taru Garg et al.
Dermatology online journal, 17(5), 3-3 (2011-06-04)
Linear porokeratosis is a rare disorder of keratinization that usually presents at birth. We report a 17-year-old male with generalized linear porokeratosis, a very rare variant of porokeratosis, with extensive involvement of the trunk and extremities along with nail and
Christoffer Ingves et al.
Scandinavian journal of plastic and reconstructive surgery and hand surgery, 37(5), 293-295 (2003-12-03)
We report the successful outcome of treatment of a basal cell carcinoma (BCC) with topical imiquimod and systemic acitretin in a 48-year-old woman. We think that this treatment is a possible option for management of these non-life-threatening tumours. Experimental evidence
A Hernández-Núñez et al.
Clinical and experimental dermatology, 26(3), 256-259 (2001-06-26)
We report a patient who presented with an intensely pruritic rash, with hyperpigmentation of the whole back and multiple hyperpigmented and hyperkeratotic papules over his forearms and lower extremities. Histologically, he showed deposits of amyloid that reacted positively with monoclonal
Lauren K Dunn et al.
Journal of drugs in dermatology : JDD, 10(7), 772-782 (2011-07-02)
Acitretin is a systemic retinoid drug used in the treatment of severe psoriasis. It has also been used for a spectrum of other difficult-to-treat dermatoses, including hyperkeratotic and inflammatory dermatoses and non-melanoma skin cancers. Here we review the available data
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