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Merck

44707

Acitretin

≥98.0% (HPLC)

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.25
PubChem Substance ID:
57650239
UNSPSC Code:
41116107
EC Number:
259-474-4
MDL number:
MFCD00866632

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InChI key

IHUNBGSDBOWDMA-AQFIFDHZSA-N

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+

SMILES string

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

assay

≥98.0% (HPLC)

form

powder

Quality Level

100

Gene Information

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

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Application

Acitretin, a retinoid that binds to nuclear receptors and regulates gene expression, is a potent activator of the α-secretase ADAM10 gene expression and apoptosis inducer via the CD95 signalling pathway. Acitretin is a systemic retinoid drug used in the treatment of severe psoriasis.

Biochem/physiol Actions

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

signalword

Danger

Hazard Classifications

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

wgk

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Storage Class

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW6084
BCBS1309V
BCBM5742V
BCBM2107V
BCBL5399V

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David Holthoewer et al.
Neuro-degenerative diseases, 10(1-4), 224-228 (2012-02-04)
ADAM10 (a disintegrin and metalloproteinase 10) has been demonstrated to act as the main physiological α-secretase. Enzymatic activity of the α-secretase on the one hand prevents the formation of toxic Aβ peptides and on the other hand promotes the secretion
Justin D Lutz et al.
Biochemical pharmacology, 77(2), 258-268 (2008-11-11)
Retinoic acid (RA) is a critical signaling molecule that performs multiple functions required to maintain cellular viability. It is also used in the treatment of some cancers. Enzymes in the CYP26 family are thought to be responsible for the elimination
Howa Yeung et al.
Journal of the American Academy of Dermatology, 68(1), 64-72 (2012-08-01)
Despite widespread dissatisfaction and low treatment persistence in moderate to severe psoriasis, patients' reasons behind treatment discontinuation remain poorly understood. We sought to characterize patient-reported reasons for discontinuing commonly used treatments for moderate to severe psoriasis in real-world clinical practice.
Filomena S G Silva et al.
Toxicology, 306, 93-100 (2013-02-07)
Acitretin is a synthetic retinoid used for severe extensive psoriasis and it has been shown to be an effective and a safe therapeutic drug for other diseases including cancer when used in combination with other agents. However, cases of acitretin-associated
Systemic retinoid therapy for chemoprevention of nonmelanoma skin cancer in a patient treated with vemurafenib.
Rachael Anforth et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 30(19), e165-e167 (2012-06-06)
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