tazarotene   Click here for help

GtoPdb Ligand ID: 6952

Synonyms: AGN-190168 | Tazorac® | Zorac®
Approved drug
tazarotene is an approved drug (FDA (1997))
Compound class: Synthetic organic
Comment: Tazarotene is a vitamin A-like retinoid that binds all isoforms of the retinoic acid receptor, but may show selectivity for the β, and γ isoforms acting via which may result in altered gene expression that provides the beneficial effects on skin condition. Tazarotene is essentailly a prodrug, with tazarotenic acid (PubChem CID 147525) being the active metabolite.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 64.49
Molecular weight 351.13
XLogP 5.62
No. Lipinski's rules broken 1
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Canonical SMILES CCOC(=O)c1ccc(nc1)C#Cc1ccc2c(c1)C(C)(C)CCS2
Isomeric SMILES CCOC(=O)c1ccc(nc1)C#Cc1ccc2c(c1)C(C)(C)CCS2
InChI 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
Bioactivity Comments
Tazarotene appears to have highest affinity for the retinoic acid receptor-β [1].
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Retinoic acid receptor-β Primary target of this compound Hs Agonist Agonist 9.1 pEC50 - 1
pEC50 9.1 (EC50 8x10-10 M) [1]
Retinoic acid receptor-γ Primary target of this compound Hs Agonist Agonist 7.4 pEC50 - 1
pEC50 7.4 (EC50 4x10-8 M) [1]
Retinoic acid receptor-α Primary target of this compound Hs Agonist Agonist 7.2 pEC50 - 1
pEC50 7.2 (EC50 6.3x10-8 M) [1]