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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
L Guenther
Journal of the American Academy of Dermatology, 43(2 Pt 3), S36-S42 (2000-07-18)
In the hope of increasing efficacy and improving safety, several combination regimens involving tazarotene gel have been explored for the treatment of plaque psoriasis. A number of large-scale studies have shown that the adjunctive use of a mid-potency or high-potency
Jorge Viera-Vera et al.
Biomolecules, 9(12) (2019-12-19)
Almost every organism has the ability of repairing damaged tissues or replacing lost and worn out body parts, nevertheless the degree of the response substantially differs between each species. Adult sea cucumbers from the Holothuria glaberrima species can eviscerate various
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