Tazarotene | CAS#118292-40-3 | Retinoid

MedKoo Cat#: 318793 | Name: Tazarotene

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Tazarotene

CAS#118292-40-3

Theoretical Analysis

MedKoo Cat#: 318793

Name: Tazarotene

CAS#: 118292-40-3

Chemical Formula: C21H21NO2S

Exact Mass: 351.1293

Molecular Weight: 351.46

Elemental Analysis: C, 71.77; H, 6.02; N, 3.99; O, 9.10; S, 9.12

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 425.00	Ready to ship
100mg	USD 650.00	Ready to ship
500mg	USD 1,450.00	Ready to ship
1g	USD 1,950.00	Ready to ship
2g	USD 2,950.00	2 Weeks

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Related CAS #

No Data

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C9R08B06

QC Data

View QC data: current batch, Lot#C9R08B06

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	142.26

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

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.

1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Tazarotene. 2024 Oct 15. PMID: 29999727. 2: Comparison table: Some drugs for plaque psoriasis. Med Lett Drugs Ther. 2024 Sep 30;66(1712):e160-e166. doi: 10.58347/tml.2024.1712b. PMID: 39302349. 3: Drugs for plaque psoriasis. Med Lett Drugs Ther. 2024 Sep 30;66(1712):153-160. doi: 10.58347/tml.2024.1712a. PMID: 39302348. 4: Corrigendum to Treatment of Palmoplantar Pustulosis Using Fixed Combination Halobetasol Propionate 0.01% and Tazarotene 0.045% Lotion: A Case Report. J Psoriasis Psoriatic Arthritis. 2023 Oct;8(4):186. doi: 10.1177/24755303231196711. Epub 2023 Aug 31. Erratum for: doi: 10.1177/2475530320950290. PMID: 39295828; PMCID: PMC11361545. 5: Thakur S, Anjum MM, Jaiswal S, Kumar A, Deepak P, Anand S, Singh S, Rajinikanth PS. Correction to "Novel Synergistic Approach: Tazarotene- Calcipotriol-Loaded-PVA/PVP-Nanofiber Incorporated in Hydrogel Film for Management and Treatment of Psoriasis". Mol Pharm. 2024 Sep 2;21(9):4754-4756. doi: 10.1021/acs.molpharmaceut.4c00635. Epub 2024 Aug 21. Erratum for: Mol Pharm. 2023 Feb 6;20(2):997-1014. doi: 10.1021/acs.molpharmaceut.2c00713. PMID: 39167386. 6: Podwojniak A, Tan IJ, Sauer J, Parikh A, Cohen BA, Heath C. Updates on Topical Dyad and Triple Combination Therapies Approved for Acne Vulgaris. Cureus. 2024 May 31;16(5):e61413. doi: 10.7759/cureus.61413. PMID: 38947674; PMCID: PMC11214703. 7: Kakpovbia EE, Young T, Milam EC, Qian Y, Yassin S, Nicholson J, Hu J, Troxel AB, Nagler AR. Efficacy of topical treatments for mild-to-moderate acne: A systematic review and meta-analysis of randomized control trials. J Eur Acad Dermatol Venereol. 2024 Jun 29. doi: 10.1111/jdv.20154. Epub ahead of print. PMID: 38943431. 8: Wang CH, Tzeng IS, Wang LK, Wu CC, Chen ML, Kuo CY, Shyu RY, Tsai FM. Tazarotene-induced Gene 1 Induces Melanoma Cell Death by Triggering Endoplasmic Reticulum Stress Response. Front Biosci (Landmark Ed). 2024 Jun 24;29(6):233. doi: 10.31083/j.fbl2906233. PMID: 38940043. 9: Guenther L, Turchin I, Vender R, Albrecht LE, Maari C, Yanofsky H, Prajapati VH. Canadian Expert Consensus on the Use of Halobetasol Propionate/Tazarotene Lotion for Plaque Psoriasis. Dermatol Ther (Heidelb). 2024 Jul;14(7):1917-1928. doi: 10.1007/s13555-024-01204-1. Epub 2024 Jun 25. PMID: 38916719; PMCID: PMC11264667. 10: Das K, Ranjan R, Kumar P, Chandra S. A Comparative Study of the Effectiveness and Safety of Topical Calcipotriol and Topical Methotrexate in Chronic Plaque Psoriasis. Cureus. 2024 May 8;16(5):e59878. doi: 10.7759/cureus.59878. PMID: 38854231; PMCID: PMC11157480. 11: Kshirsagar SM, Shrestha N, Kipping T, Banga AK. Formulation development of tazarotene-loaded PLGA nanoparticles for follicular delivery in the treatment of inflammatory skin diseases. Eur J Pharm Biopharm. 2024 Jul;200:114346. doi: 10.1016/j.ejpb.2024.114346. Epub 2024 May 31. PMID: 38823541. 12: Shergill M, Ali MU, Abu-Hilal M. Comparison of the Efficacy of Clascoterone, Trifarotene, and Tazarotene for the Treatment of Acne: A Systematic Literature Review and Meta-Analysis. Dermatol Ther (Heidelb). 2024 May;14(5):1093-1102. doi: 10.1007/s13555-024-01175-3. Epub 2024 May 11. PMID: 38733511; PMCID: PMC11116292. 13: See JA, Chavda R, Kon KM, Goodman GJ, Oblepias MS, Nadela RE, Oon HH, Aurangabadkar S, Suh DH, Chan HHL, Lahiri K. A review of the topical management of acne and its associated sequelae in the Asia-Pacific region with a spotlight on trifarotene. Int J Dermatol. 2024 Jun;63(6):704-713. doi: 10.1111/ijd.17141. Epub 2024 Apr 21. PMID: 38643368. 14: Nofal H, Omran F, ElKholy B, Nofal S, Nofal A. Tazarotene is as effective and well-tolerated as imiquimod in the treatment of verruca plana: a comparative randomized controlled trial. Clin Exp Dermatol. 2024 Sep 18;49(10):1197-1204. doi: 10.1093/ced/llae133. PMID: 38618753. 15: Curtis KL, Lipner SR. Vitamins for the Management of Nail Disease: A Literature Review. Skin Appendage Disord. 2024 Apr;10(2):104-122. doi: 10.1159/000534972. Epub 2023 Nov 23. PMID: 38572190; PMCID: PMC10987071. 16: Alomary SA, Pei M, Lipner SR. Retinoids and Risk: A FAERS Database Study of Topical Retinoids. J Cutan Med Surg. 2024 Jul-Aug;28(4):393-394. doi: 10.1177/12034754241239269. Epub 2024 Mar 11. PMID: 38468210. 17: Nahm WJ, Badiavas EV, Kirsner RS, Boyd CJ, Arthur AA, Bae S, Shen J. Atypical Fibroxanthoma Treated with a Topical Combination of Imiquimod, Tazarotene, and 5-Fluorouracil. Dermatol Ther (Heidelb). 2024 Apr;14(4):1049-1056. doi: 10.1007/s13555-024-01127-x. Epub 2024 Mar 12. PMID: 38467988; PMCID: PMC11052744. 18: Sidhu JK, Matreja PS, Gupta AK, Singh A, Singh S. Head-to-Head Comparison of Tazarotene and Calcitriol with or without Sequential Therapy in Mild-to-Moderate Psoriasis: A Randomized Open-label Study. J Res Pharm Pract. 2024 Jan 31;12(2):44-48. doi: 10.4103/jrpp.jrpp_10_23. PMID: 38463187; PMCID: PMC10923203. 19: Cheng Q, Wang W, Dong X, Chai Y, Goto T, Tu R, Yan L, Yu A, Dai H. An Adaptable Drug Delivery System Facilitates Peripheral Nerve Repair by Remodeling the Microenvironment. Biomacromolecules. 2024 Mar 11;25(3):1509-1526. doi: 10.1021/acs.biomac.3c01094. Epub 2024 Feb 20. PMID: 38376392. 20: Iliopoulos F, Tu D, Pence IJ, Li X, Ghosh P, Luke MC, Raney SG, Rantou E, Evans CL. Determining topical product bioequivalence with stimulated Raman scattering microscopy. J Control Release. 2024 Mar;367:864-876. doi: 10.1016/j.jconrel.2024.02.010. Epub 2024 Feb 19. PMID: 38346503.