Tazarotene
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MedKoo CAT#: 318793

CAS#: 118292-40-3

Description: Tazarotene is a third-generation prescription topical retinoid. Tazarotene is a retinoid prodrug which is converted to its active form, the cognate carboxylic acid of tazarotene, by rapid deesterification in animals and humans. Tazarotenic acid binds to all three members of the retinoic acid receptor (RAR) family: RARα, RARβ, and RARγ but shows relative selectivity for RARβ, and RARγ and may modify gene expression.

Chemical Structure

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Tazarotene
CAS# 118292-40-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318793
Name: Tazarotene
CAS#: 118292-40-3
Chemical Formula: C21H21NO2S
Exact Mass: 351.13
Molecular Weight: 351.464
Elemental Analysis: C, 71.77; H, 6.02; N, 3.99; O, 9.10; S, 9.12

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 425 Ready to ship
100mg USD 650 Ready to ship
500mg USD 1450 Ready to ship
1g USD 1950 Ready to ship
2g USD 2950 2 Weeks
Bulk inquiry

Synonym: AGN190168, AGN-190168; AGN 190168, Tazarotene, Fabior, Zorac

IUPAC/Chemical Name: ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate

InChi Key: OGQICQVSFDPSEI-UHFFFAOYSA-N

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

SMILES Code: O=C(OCC)C1=CN=C(C#CC2=CC(C(C)(C)CCS3)=C3C=C2)C=C1

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Tazarotene (AGN 190168) is a selective retinoic acid receptor (RAR) agonist.
In vitro activity: To determine the effect of tazarotene on cell growth, human BCC cells were treated with various doses of tazarotene for 12, 24, or 48 h, and cell viability was measured using the MTT assay. As shown in Figure 1A, tazarotene significantly reduces BCC cell viability in a dose- and time-dependent manner. To determine whether tazarotene-induced growth inhibition occurs via cell cycle blockade, BCC cells were subjected to flow cytometric analysis. BCC cells were exposed to a series of different tazarotene concentrations for 12, 24, or 48 h. Figure 1B shows that 25 and 50 μM tazarotene treatment for 12 h and 25 μM tazarotene treatment for 24 h caused transient G0/G1 phase cell cycle arrest. In addition, the sub-G1 population, which is typically considered an apoptosis-related hypodiploid DNA content peak, significantly increased in a dose-dependent manner at 12, 24, and 48 h after tazarotene treatment. To further confirm the observed tazarotene-induced apoptosis, we utilized flow cytometry to analyze TUNEL staining in cells treated with various concentrations of tazarotene for 24 h. As shown in Figure 1C, the percentage of TUNEL-positive BCC cells increased in a concentration-dependent manner. Taken together, these observations suggest that the anti-proliferative effect of tazarotene in BCC cells results, at least in part, from its ability to induce apoptosis. DNA Cell Biol. 2014 Oct;33(10):652-66. https://pubmed.ncbi.nlm.nih.gov/24927175/
In vivo activity: Therefore, it has been tested whether tazarotene would affect BCCs (basal cell carcinoma) in Ptch1+/− mice in a controlled chemoprevention trial. Consistent with our previous experience (10) , all Ptch1+/− mice treated with vehicle control cream and exposed to UV or IR developed microscopic BCCs (Fig. 1) ⇓ . In the first UV study, Ptch1+/− mice treated topically with 0.1% tazarotene had fewer microscopic BCCs per centimeter of skin surface length than did those in the vehicle control group after 5 months of UV radiation at 7 months of age (1.05 versus 3.9; P < 0.03); after 7 months of UV radiation at 9 months of age (0.46 versus 3.48; P < 0.0001), and after 9 months of UV radiation at 11 months of age (0.51 versus 3.79; P < 0.011; Fig. 1A ⇓ ). The average cross-sectional BCC size in the mice treated with tazarotene was also smaller than that in control animals after 5 months of UV radiation at 7 months of age (2.5 versus 9.1 μm2; P < 0.0001); after 7 months of UV radiation at 9 months of age (2.4 versus 17 μm2; P < 0.0001), and after 9 months of UV radiation at 11 months of age (3.5 versus 54 μm2; P < 0.0023; Fig. 1B ⇓ ). Also, in many skin biopsies, topical tazarotene treatment resulted in a thicker epidermis, as compared with control vehicle-treated mice (Fig. 3) ⇓ . Topical tazarotene treatment did not affect the normal weight gain of the UV- or IR-treated mice (data not shown).Tazarotene is a promising agent for skin cancer prevention in populations at risk for BCCs, such as patients with the basal cell nevus syndrome. Cancer Res. 2004 Jul 1;64(13):4385-9. https://cancerres.aacrjournals.org/content/64/13/4385.long

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 142.26

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 the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Wu CS, Chen GS, Lin PY, Pan IH, Wang ST, Lin SH, Yu HS, Lin CC. Tazarotene induces apoptosis in human basal cell carcinoma via activation of caspase-8/t-Bid and the reactive oxygen species-dependent mitochondrial pathway. DNA Cell Biol. 2014 Oct;33(10):652-66. doi: 10.1089/dna.2014.2366. Epub 2014 Jun 13. PMID: 24927175; PMCID: PMC4179923. 2. Al Haj Zen A, Nawrot DA, Howarth A, Caporali A, Ebner D, Vernet A, Schneider JE, Bhattacharya S. The Retinoid Agonist Tazarotene Promotes Angiogenesis and Wound Healing. Mol Ther. 2016 Oct;24(10):1745-1759. doi: 10.1038/mt.2016.153. Epub 2016 Aug 2. PMID: 27480772; PMCID: PMC5112045. 3. So PL, Lee K, Hebert J, Walker P, Lu Y, Hwang J, Kopelovich L, Athar M, Bickers D, Aszterbaum M, Epstein EH Jr. Topical tazarotene chemoprevention reduces Basal cell carcinoma number and size in Ptch1+/- mice exposed to ultraviolet or ionizing radiation. Cancer Res. 2004 Jul 1;64(13):4385-9. doi: 10.1158/0008-5472.CAN-03-1927. PMID: 15231643. 4. Hsia E, Johnston MJ, Houlden RJ, Chern WH, Hofland HE. Effects of topically applied acitretin in reconstructed human epidermis and the rhino mouse. J Invest Dermatol. 2008 Jan;128(1):125-30. doi: 10.1038/sj.jid.5700968. Epub 2007 Jul 19. PMID: 17637822.
In vitro protocol: 1. Wu CS, Chen GS, Lin PY, Pan IH, Wang ST, Lin SH, Yu HS, Lin CC. Tazarotene induces apoptosis in human basal cell carcinoma via activation of caspase-8/t-Bid and the reactive oxygen species-dependent mitochondrial pathway. DNA Cell Biol. 2014 Oct;33(10):652-66. doi: 10.1089/dna.2014.2366. Epub 2014 Jun 13. PMID: 24927175; PMCID: PMC4179923. 2. Al Haj Zen A, Nawrot DA, Howarth A, Caporali A, Ebner D, Vernet A, Schneider JE, Bhattacharya S. The Retinoid Agonist Tazarotene Promotes Angiogenesis and Wound Healing. Mol Ther. 2016 Oct;24(10):1745-1759. doi: 10.1038/mt.2016.153. Epub 2016 Aug 2. PMID: 27480772; PMCID: PMC5112045.
In vivo protocol: 1. So PL, Lee K, Hebert J, Walker P, Lu Y, Hwang J, Kopelovich L, Athar M, Bickers D, Aszterbaum M, Epstein EH Jr. Topical tazarotene chemoprevention reduces Basal cell carcinoma number and size in Ptch1+/- mice exposed to ultraviolet or ionizing radiation. Cancer Res. 2004 Jul 1;64(13):4385-9. doi: 10.1158/0008-5472.CAN-03-1927. PMID: 15231643. 2. Hsia E, Johnston MJ, Houlden RJ, Chern WH, Hofland HE. Effects of topically applied acitretin in reconstructed human epidermis and the rhino mouse. J Invest Dermatol. 2008 Jan;128(1):125-30. doi: 10.1038/sj.jid.5700968. Epub 2007 Jul 19. PMID: 17637822.

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1: Gregoriou S, Kritsotaki E, Katoulis A, Rigopoulos D. Use of tazarotene foam for the treatment of acne vulgaris. Clin Cosmet Investig Dermatol. 2014 May 27;7:165-70. doi: 10.2147/CCID.S37327. eCollection 2014. Review. PubMed PMID: 24920932; PubMed Central PMCID: PMC4043801.

2: Talpur R, Cox K, Duvic M. Efficacy and safety of topical tazarotene: a review. Expert Opin Drug Metab Toxicol. 2009 Feb;5(2):195-210. Review. PubMed PMID: 20213916.

3: Ogden S, Samuel M, Griffiths CE. A review of tazarotene in the treatment of photodamaged skin. Clin Interv Aging. 2008;3(1):71-6. Review. PubMed PMID: 18488880; PubMed Central PMCID: PMC2544371.

4: Weindl G, Roeder A, Schäfer-Korting M, Schaller M, Korting HC. Receptor-selective retinoids for psoriasis: focus on tazarotene. Am J Clin Dermatol. 2006;7(2):85-97. Review. PubMed PMID: 16605289.

5: Dando TM, Wellington K. Topical tazarotene: a review of its use in the treatment of plaque psoriasis. Am J Clin Dermatol. 2005;6(4):255-72. Review. PubMed PMID: 16060713.

6: Saini R, Tutrone WD, Weinberg JM. Advances in therapy for psoriasis: an overview of infliximab, etanercept, efalizumab, alefacept, adalimumab, tazarotene, and pimecrolimus. Curr Pharm Des. 2005;11(2):273-80. Review. PubMed PMID: 15638763.

7: Singh F, Weinberg JM. Oral tazarotene and oral pimecrolimus: novel oral therapies in development for psoriasis. J Drugs Dermatol. 2004 Mar-Apr;3(2):141-3. Review. PubMed PMID: 15098968.

8: Roeder A, Schaller M, Schäfer-Korting M, Korting HC. Tazarotene: therapeutic strategies in the treatment of psoriasis, acne and photoaging. Skin Pharmacol Physiol. 2004 May-Jun;17(3):111-8. Review. PubMed PMID: 15087589.

9: Henno A, Hua MT, de la Brassinne M. [Medication of the month. Tazarotene 0.05%-0.1% (Zorac)]. Rev Med Liege. 2003 Nov;58(11):706-8. Review. French. PubMed PMID: 14748200.

10: Koo J, Behnam SE, Behnam SM. The efficacy of topical tazarotene monotherapy and combination therapies in psoriasis. Expert Opin Pharmacother. 2003 Dec;4(12):2347-54. Review. PubMed PMID: 14640932.

11: Guenther LC. Optimizing treatment with topical tazarotene. Am J Clin Dermatol. 2003;4(3):197-202. Review. PubMed PMID: 12627995.

12: Guenther LC. Topical tazarotene therapy for psoriasis, acne vulgaris, and photoaging. Skin Therapy Lett. 2002 Mar;7(3):1-4. Review. PubMed PMID: 12007011.

13: Kakita L. Tazarotene versus tretinoin or adapalene in the treatment of acne vulgaris. J Am Acad Dermatol. 2000 Aug;43(2 Pt 3):S51-4. Review. PubMed PMID: 10898831.

14: Lebwohl M. Strategies to optimize efficacy, duration of remission, and safety in the treatment of plaque psoriasis by using tazarotene in combination with a corticosteroid. J Am Acad Dermatol. 2000 Aug;43(2 Pt 3):S43-6. Review. PubMed PMID: 10898829.

15: Guenther L. Tazarotene combination treatments in psoriasis. J Am Acad Dermatol. 2000 Aug;43(2 Pt 3):S36-42. Review. PubMed PMID: 10898828.

16: Menter A. Pharmacokinetics and safety of tazarotene. J Am Acad Dermatol. 2000 Aug;43(2 Pt 3):S31-5. Review. PubMed PMID: 10898827.

17: Marks R. The role of tazarotene in the treatment of psoriasis. Br J Dermatol. 1999 Apr;140 Suppl 54:24-8. Review. PubMed PMID: 10731131.

18: Tazarotene--a topical retinoid for psoriasis. Drug Ther Bull. 1999 Jun;37(6):47-8. Review. PubMed PMID: 10692712.

19: Tang-Liu DD, Matsumoto RM, Usansky JI. Clinical pharmacokinetics and drug metabolism of tazarotene: a novel topical treatment for acne and psoriasis. Clin Pharmacokinet. 1999 Oct;37(4):273-87. Review. PubMed PMID: 10554045.

20: Weinstein GD. The management of psoriasis-tazarotene: the bottom line. Cutis. 1998 Feb;61(2 Suppl):38-9. Review. PubMed PMID: 9787992.