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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

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)
Afficher tous les articles scientifiques apparentés

Articles

Retinoic Acid and Gene Expression

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

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