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44707

Sigma-Aldrich

Acitretin

≥98.0% (HPLC)

Synonyme(s) :

9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

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About This Item

Formule empirique (notation de Hill):
C21H26O3
Numéro CAS:
55079-83-9
Poids moléculaire :
326.43
Numéro CE :
259-474-4
Numéro MDL:
MFCD00866632
Code UNSPSC :
41116107
ID de substance PubChem :
57650239
Nomenclature NACRES :
NA.25

Pureté

≥98.0% (HPLC)

Forme

powder

Chaîne SMILES 

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+

Clé InChI

IHUNBGSDBOWDMA-AQFIFDHZSA-N

Informations sur le gène

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.

Actions biochimiques/physiologiques

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

Pictogrammes

Exclamation markHealth hazardEnvironment
GHS07,GHS08,GHS09

Mention d'avertissement

Danger

Mentions de danger

H315 - H319 - H360 - H410

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Retinyl acetate synthetic, crystalline solid or supercooled liquid

Sigma-Aldrich

R4632

Retinyl acetate

all trans-Retinal powder, ≥98%

Sigma-Aldrich

R2500

all trans-Retinal

Acide rétinoïque ≥98% (HPLC), powder

Sigma-Aldrich

R2625

Acide rétinoïque

Sandra Philipp et al.
Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology : JDDG, 10(11), 821-837 (2012-09-01)
Monotherapy with TNF-α inhibitors does not always produce a sufficient response in psoriasis patients. Combinations of TNF-α antagonists such as adalimumab with systemic antipsoriatic therapies such as methotrexate are not approved for use in psoriasis, and the published data are
Justin Cheeley et al.
Journal of the American Academy of Dermatology, 68(2), 247-254 (2012-08-25)
Bexarotene is the only Food and Drug Administration-approved retinoid for the treatment of cutaneous T-cell lymphoma (CTCL) and is associated with a relatively high frequency of adverse effects. Acitretin has anecdotally been reported to be effective for CTCL. We sought
Vincenzo Bettoli et al.
The Journal of dermatological treatment, 24(3), 235-237 (2012-11-15)
The chemoprevention refers to the use of various types of chemical agents for preventing carcinogenic progression. Systemic retinoids are the most studied chemopreventive agents due to their capacity to regulate cell proliferation and their demonstrated efficacy in several clinical studies.
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
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.
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