Tazarotene

  • CAT Number: A000814
  • CAS Number: 118292-40-3
  • Molecular Formula: C21H21NO2S
  • Molecular Weight: 351.46
  • Purity: ≥95%
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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.

Catalog Number A000814
CAS Number 118292-40-3
Molecular Formula

C21H21NO2S

Purity 95%
Target RARs
Solubility >14.9mg/mL in DMSO
Storage -20°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
InChIKey OGQICQVSFDPSEI-UHFFFAOYSA-N
SMILES CCOC(=O)C1=CN=C(C=C1)C#CC2=CC3=C(C=C2)SCCC3(C)C
Reference

1: Maiti R, Sirka CS, Ashique Rahman MA, Srinivasan A, Parida S, Hota D. Efficacy
and Safety of Tazarotene 0.1% Plus Clindamycin 1% Gel Versus Adapalene 0.1% Plus
Clindamycin 1% Gel in Facial Acne Vulgaris: A Randomized, Controlled Clinical
Trial. Clin Drug Investig. 2017 Nov;37(11):1083-1091. doi:
10.1007/s40261-017-0568-2. PubMed PMID: 28913735.

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2: Paolino G, Muscardin LM, Donati M, Didona D, Panetta C, Donati P. Complete
regression of keratoacanthoma with topical tazarotene gel 0.1%: therapeutic and
pathophysiological perspectives. G Ital Dermatol Venereol. 2017 Sep 8. doi:
10.23736/S0392-0488.17.05718-2. [Epub ahead of print] PubMed PMID: 28895378.

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3: Hanson B, Becker L, Hook K, Polcari I, Areaux RG Jr, Maguiness S. Ectropion
Improvement with Topical Tazarotene in Children with Lamellar Ichthyosis. Pediatr
Dermatol. 2017 Sep;34(5):584-589. doi: 10.1111/pde.13240. Epub 2017 Aug 17.
PubMed PMID: 28815772.
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4: Behera B, Chandrashekar L, Singh N, Thappa DM, Gochhait D. Lamellar ichthyosis
associated bilateral pseudoainhum of fingers and toes successfully treated with
tazarotene. Dermatol Ther. 2017 Sep;30(5). doi: 10.1111/dth.12516. Epub 2017 Jul
21. PubMed PMID: 28730635.
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5: Prasad V, Chaurasia S. Performance evaluation of non-ionic surfactant based
tazarotene encapsulated proniosomal gel for the treatment of psoriasis. Mater Sci
Eng C Mater Biol Appl. 2017 Oct 1;79:168-176. doi: 10.1016/j.msec.2017.05.036.
Epub 2017 May 8. PubMed PMID: 28629004.
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6: Sugarman JL, Gold LS, Lebwohl MG, Pariser DM, Alexander BJ, Pillai R. A Phase
2, Multicenter, Double-Blind, Randomized, Vehicle Controlled Clinical Study to
Assess the Safety and Efficacy of a Halobetasol/Tazarotene Fixed Combination in
the Treatment of Plaque Psoriasis. J Drugs Dermatol. 2017 Mar 1;16(3):197-204.
PubMed PMID: 28301614.
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7: Menzies S, Mc Menamin M, Barry R. Lentigo maligna successfully treated with
combination therapy of topical tazarotene and imiquimod. Clin Exp Dermatol. 2017
Mar 1. doi: 10.1111/ced.13053. [Epub ahead of print] PubMed PMID: 28247492.

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8: Shyu RY, Wang CH, Wu CC, Chen ML, Lee MC, Wang LK, Jiang SY, Tsai FM.
Tazarotene-Induced Gene 1 Enhanced Cervical Cell Autophagy through Transmembrane
Protein 192. Mol Cells. 2016 Dec;39(12):877-887. doi:
10.14348/molcells.2016.0161. Epub 2016 Dec 13. PubMed PMID: 27989102; PubMed
Central PMCID: PMC5223105.
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9: Cai Q, Huang Z, Qi L, Wang T, Shen Y, Huang J. Tazarotene-induced gene 2 is
associated with poor survival in non-small cell lung cancer. Oncol Lett. 2016
Oct;12(4):2680-2685. Epub 2016 Aug 16. PubMed PMID: 27698842; PubMed Central
PMCID: PMC5038457.

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10: 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. PubMed PMID: 27480772; PubMed Central PMCID: PMC5112045.

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