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Compound Detail

CHEMBL259571

TAPINAROF
💊 Approved Drug
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💊 Approved Drug
CC(C)c1c(O)cc(/C=C/c2ccccc2)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL259571
Name TAPINAROF
Phase Approved
Structure Type MOL
InChI Key ZISJNXNHJRQYJO-CMDGGOBGSA-N
Therapeutic ✓ Yes

Known Names

Benvitimod GSK-2894512 GSK2894512 Tapinarof Vtama Wbi-1001
2
Targets
4
Activities
2
Assay Types
0
PK Parameters
17
Publications
6
Known Names
2
Indications
1
Mechanisms

Molecular Properties

254.3
MW (Da)
4.39
ALogP
2
HBA
2
HBD
40.5
PSA (Ų)
0.80
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2022
Availability Prescription
Chirality Achiral

Routes of Administration

Topical

Flags

Natural Product First in Class
USAN Year 2017

Extended Properties

Molecular Formula C17H18O2
MW 254.33
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness 0.47

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Aryl hydrocarbon receptor agonist AGONIST Aryl hydrocarbon receptor ✓ ✓

Indications

Psoriasis Dermatitis, Atopic

ATC Classification

D05AX07
tapinarof
Level 1: DERMATOLOGICALS
Level 2: ANTIPSORIATICS

Activity Summary

EC50 3 meas. best 7.89
IC50 1 meas. best 5.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aryl hydrocarbon receptor
CHEMBL3201
 EC50 7.89 7.6733 13.0 3
CD4+ve Th
CHEMBL613544
 IC50 5.28 5.28 5200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aryl hydrocarbon receptor EC50 = 13.0 nM 7.89 Agonist activity at human AhR by TR-FRET assay 39137454
Aryl hydrocarbon receptor EC50 = 27.0 nM 7.57 Agonist activity at AHR in human HepG2-Lucia AhR cells stably transfected with D... 37348572
Aryl hydrocarbon receptor EC50 = 27.34 nM 7.56 Agonist activity at AhR in human recombinant HepG2-Lucia AhR cell incubated for ... 35123295
CD4+ve Th IC50 = 5200.0 nM 5.28 Induction of apoptosis in human CD4+ve Th cells 35123295

Literature References

PubMed DOI Target Context # Activities
17284598 10.1073/pnas.0610525104 Photorhabdus luminescens 6
18407564 10.1002/ps.1591 Caenorhabditis elegans 2
37348572 10.1016/j.bmcl.2023.129383 Aryl hydrocarbon receptor 2
35123295 10.1016/j.ejmech.2022.114122 Aryl hydrocarbon receptor 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
39137454 10.1016/j.ejmech.2024.116759 Aryl hydrocarbon receptor 1
37348572 10.1016/j.bmcl.2023.129383 Mus musculus 1
- 10.6019/EOS300108 HepG2 1
35123295 10.1016/j.ejmech.2022.114122 CD4+ve Th 1
36459434 10.1021/acs.jmedchem.2c00956 Unchecked 1
17284598 10.1073/pnas.0610525104 Prophenoloxidase 1
25988621 10.1021/np500974f Escherichia coli 1
25988621 10.1021/np500974f Saccharomyces cerevisiae 1
25988621 10.1021/np500974f Bacillus subtilis 1
17284598 10.1073/pnas.0610525104 Hemolymph 1
17284598 10.1073/pnas.0610525104 Manduca sexta 1

Data from ChEMBL 36 via Core Engine