Tazarotene

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Cat.No. 3997 - Tazarotene | C21H21NO2S | CAS No. 118292-40-3
Description: Receptor-selective retinoid; binds RAR-β and -γ
Chemical Name: 6-[2-(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic acid ethyl ester
Purity: ≥99% (HPLC)
Datasheet
Citations
Literature

Biological Activity

Receptor-selective acetylenic retinoid; binds at retinoid acid receptors (RAR) -β and -γ. Topically used for the treatment of skin disorders, particularly psoriasis and acne. Implicated in the treatment of basal cell carcinomas; induces upregulation of Bax in vivo. Exhibits antiproliferative and proapoptotic activity. Upregulates TIGs (Tazarotene-induced genes), including the cell adhesion molecule TIG1 and the tumor-suppressor TIG3.

Technical Data

M. Wt 351.46
Formula C21H21NO2S
Storage Store at +4°C
Purity ≥99% (HPLC)
CAS Number 118292-40-3
PubChem ID 5381
InChI Key OGQICQVSFDPSEI-UHFFFAOYSA-N
Smiles CC1(C)C2=C(C=CC(C#CC3=NC=C(C(OCC)=O)C=C3)=C2)SCC1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 35.15 100
ethanol 17.57 50

Preparing Stock Solutions

The following data is based on the product molecular weight 351.46. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.85 mL 14.23 mL 28.45 mL
5 mM 0.57 mL 2.85 mL 5.69 mL
10 mM 0.28 mL 1.42 mL 2.85 mL
50 mM 0.06 mL 0.28 mL 0.57 mL

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Product Datasheets

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References

References are publications that support the products' biological activity.

Higuchi et al (2003) Induction of TIG3, a putative class II tumor suppressor gene, by retinoic acid in head and neck and lungcarcinoma cells and its association with suppression of the transformed phenotype. Oncogene 22 4627 PMID: 12879006

Orlandi et al (2004) Evidence of increased apoptosis and reduced proliferation in basal cell carcinomas treated with Tazarotene. J.Invest.Dermatol. 122 1037 PMID: 15102095

Son et al (2009) Expression and mutation analysis of TIG1 (Tazarotene-induced gene 1) in human gastric cancer. Oncol.Res. 17 571 PMID: 19806788


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Keywords: receptor-selective retinoid RARbeta RARgamma retinoic acid receptor treats skin conditions Retinoic Acid Receptors

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Pathways for Tazarotene

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