A retinoid prodrug
Related Products
Active Metabolite(s)
21367Tazarotenic Acid
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Tazarotene

Item No. 23559

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-[2-(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic acid, ethyl ester
CAS Number
118292-40-3
Synonyms
  • AGN 190168
Molecular Formula
C21H21NO2S
Formula Weight
351.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH 7.2) (1:4): 0.2 mg/ml
λmax
259, 352 nm
SMILES
O=C(OCC)C1=CC=C(C#CC2=CC(C(C)(C)CCS3)=C3C=C2)N=C1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    5 mg

    $36

    Add

    10 mg

    $68

    Add

    50 mg

    $268

    Add

    100 mg

    $436

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Tazarotene is a retinoid prodrug of tazarotenic acid (Item No. 21367).1 It is metabolized by esterases in vivo to its active free acid form. Tazarotene (1 μM) inhibits proliferation of and collagen synthesis by human dermal fibroblasts in vitro.2 It also downregulates markers of keratinocyte differentiation, keratinocyte proliferation, and inflammation and upregulates tazarotene-induced gene 1 (TIG1) and TIG2 in patient-derived psoriatic lesion samples following topical administration.3 Tazarotene (0.1% per day, topical) induces complete reduction in skin utricle diameter in the Rhino mouse, which is a model used to test retinoid activity because its skin contains keratinized pilosebaceous structures.4 It also decreases basal cell carcinoma number and size in a Ptch1+/- mouse model of ultraviolet- or ionizing radiation-induced skin cancer when administered topically at a dose of 0.1% per day.5 Formulations containing tazarotene have been used in the treatment of psoriasis, acne, and sun-damaged skin.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chandraratna, R.A. Tazarotene-first of a new generation of receptor-selective retinoids. Br. J. Dermatol. 135(Suppl 49), 18-25 (1996).

    2. Ogawa, A., Maeguchi, M., Uchida, Y., et al. Effect of tazarotene, an acetylenic retinoid, on human dermal fibroblast. Jpn. J. Pharmacol. 76(3), 317-319 (1998).

    3. Duvic, M., Nagpal, S., Asano, A.T., et al. Molecular mechanisms of tazarotene action in psoriasis. J. Am. Acad. Dermatol. 37(2 Pt 3), S18-S24 (1997).

    4. Hsia, E.Y., Johnston, M.J., Houlden, R.J., et al. Effects of topically applied acitretin in reconstructed human epidermis and the rhino mouse. J. Invest. Dermatol. 128(1), 125-130 (2008).

    5. So, P.-L., Lee, K., Herbert, J., et al. Topical tazarotene chemoprevention reduces basal cell carcinoma number and size in Ptch1+/- mice exposed to ultraviolet or ionizing radiation. Cancer Res. 64(13), 4385-4389 (2004).