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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: tazarotene

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key OGQICQVSFDPSEI-UHFFFAOYSA-N
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.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com