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T7080

Sigma-Aldrich

Tazarotene

≥98% (HPLC)

Synonym(s):

6-[(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic acid ethyl ester, AGN-190168, ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl] nicotinate

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About This Item

Empirical Formula (Hill Notation):
C21H21NO2S
CAS Number:
118292-40-3
Molecular Weight:
351.46
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to very faintly yellow

solubility

DMSO: >15 mg/mL

originator

Allergan

storage temp.

2-8°C

InChI

1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3

InChI key

OGQICQVSFDPSEI-UHFFFAOYSA-N

Biochem/physiol Actions

Tazarotene induces the expression of tazarotene-induced gene 3 (TIG3), a tumor suppressor gene. It is a prodrug of tazarotenic acid, which specifically activates RARb and RARg, only weakly activates RARa, and is inactive at retinoid X receptors (RXRs). In psoriasis, tazarotene normalizes abnormal keratinocyte differentiation and reduces their hyperproliferation.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Allergan. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

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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A high-content imaging-based screening pipeline for the systematic identification of anti-progeroid compounds
Kubben N, et al.
Methods, 46-58 (2016)
D D Tang-Liu et al.
Clinical pharmacokinetics, 37(4), 273-287 (1999-12-20)
Tazarotene (AGN 190168) is a new acetylenic retinoid which is effective for the topical treatment of patients with stable plaque psoriasis and mild to moderate acne vulgaris. Topical gel application provides direct delivery of tazarotene into the skin. At 10
M Lebwohl
Journal of the American Academy of Dermatology, 43(2 Pt 3), S43-S46 (2000-07-18)
In the treatment of plaque psoriasis with corticosteroids, long-term efficacy and safety are often compromised by tachyphylaxis, steroid rebound, and adverse effects. However, the results of recent studies demonstrate that the use of tazarotene in conjunction with a corticosteroid can
Agata Kryczyk-Poprawa et al.
Pharmaceutics, 12(9) (2020-09-26)
Exposure of a drug to UV irradiation could affect its physicochemical properties. Hence, photostability testing is essential for topically administered drugs. Tazarotene, a receptor-selective, third-generation retinoid, is commonly used to treat acne vulgaris and psoriasis. In the present study, an
Yu-Chen Huang et al.
Lasers in surgery and medicine, 45(2), 102-107 (2013-02-21)
Nail psoriasis is difficult to treat. The efficacy of pulsed dye laser (PDL) therapy for nail psoriasis has been reported in non-placebo controlled studies. To evaluate the efficacy and safety of PDL with topical retinoid in the treatment of nail
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