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
No information available.
Summary of Clinical Use Click here for help
Tazarotene is used to treat various skin disorders such as acne and plaque psoriasis. It is also used to reduce the appearance of wrinkles and skin pigmentation (eg age related mottling and freckles). In the EU, the EMA has granted orphan designation for tazarotene (as Orfagen®) to be used for the treatment of congenital ichthyoses.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The exact mechanism of tazarotene action is unknown, but it is suggested that the drug modifies gene expression by acting through the retinoic acid receptor, perhaps acting preferentially through the β and γ isoforms. It also has some affinity for the retinoid X receptors.
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