tapinarof   Click here for help

GtoPdb Ligand ID: 9686

Synonyms: GSK-2894512 | GSK2894512 [3] | Vtama® | WB-1001 | WBI 1001 | WBI-1001
Approved drug Immunopharmacology Ligand
tapinarof is an approved drug (FDA (2022))
Compound class: Synthetic organic
Comment: Tapinarof (GSK2894512) is an aryl hydrocarbon receptor (AhR) agonist [3]. It is a naturally occurring polyphenol derived from bacteria that exist symbiotically with entomopathogenic nematodes. AhR was identified as the primary molecular target based on phenotypic screening using the DiscoveRx BioMAP Diversity Plus System and confirmed using AhR knockout mice. Tapinarof was the first steroid-free topical drug in this class to be approved as a plaque psoriasis medication.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 0
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 40.46
Molecular weight 254.13
XLogP 5.04
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES CC(c1c(O)cc(cc1O)C=Cc1ccccc1)C
Isomeric SMILES CC(c1c(O)cc(cc1O)/C=C/c1ccccc1)C
InChI InChI=1S/C17H18O2/c1-12(2)17-15(18)10-14(11-16(17)19)9-8-13-6-4-3-5-7-13/h3-12,18-19H,1-2H3/b9-8+
No information available.
Summary of Clinical Use Click here for help
Topically applied tapinarof (research code GSK2894512) demonstrated clinical efficacy in Phase 2 and Phase 3 clinical trials in patients with plaque psoriasis (PS) [1-2]. Tapinarof has also completed Phase 1 studies for atopic dermatitis. The first FDA approval (May 2022) authorised use of tapinarof (Vtama®) as a treament for PS. Unlike steroid-based anti-inflammatory drugs that are used to treat PS, tapinarof has an unlimited duration of use and can be used on sensitive body areas.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The AhR is a cytosolic ligand-activated transcription factor that senses a wide range of endogenous and exogenous molecules and influences multiple biological activities. IIn the immune system it acts as a regulator of innate and adaptive immune responses, impacting the balance of Th17 and Treg cells. Tapinarof modulates the immune response via an agonistic interaction with the AhR [3].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03983980 Tapinarof for the Treatment of Plaque Psoriasis in Adults (3002) Phase 3 Interventional Dermavant Sciences, Inc. 2
NCT03956355 Tapinarof for the Treatment of Plaque Psoriasis in Adults (3001) Phase 3 Interventional Dermavant Sciences, Inc. 2