Tapinarof

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Tapinarof
Accession Number
DB06083
Type
Small Molecule
Groups
Investigational
Description

Tapinarof is targeted as a topical cream treatment for psoriasis, a chronic autoimmune skin disease.

Structure
Thumb
Synonyms
  • 3,5-Dihydroxy-4-isopropyl-trans-stilbene
  • Benvitimod
External IDs
GSK-2894512 / GSK2894512 / WBI 1001 / WBI-1001
Categories
UNII
84HW7D0V04
CAS number
79338-84-4
Weight
Average: 254.329
Monoisotopic: 254.13067982
Chemical Formula
C17H18O2
InChI Key
ZISJNXNHJRQYJO-CMDGGOBGSA-N
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+
IUPAC Name
5-[(E)-2-phenylethenyl]-2-(propan-2-yl)benzene-1,3-diol
SMILES
CC(C)C1=C(O)C=C(\C=C\C2=CC=CC=C2)C=C1O

Pharmacology

Indication

Investigated for use/treatment in psoriasis and psoriatic disorders.

Pharmacodynamics
Not Available
Mechanism of action

WBI-1001 selectively modulates the cytokine cascade deep under the skin, a process that rapidly decreases inflammations and skin plague. It targets the four major mechanisms involved in the disease.

TargetActionsOrganism
UInterleukin-12 subunit betaNot AvailableHumans
UInterleukin-2Not AvailableHumans
UInterleukin-6Not AvailableHumans
UInterleukin-8Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Joyce SA, Brachmann AO, Glazer I, Lango L, Schwar G, Clarke DJ, Bode HB: Bacterial biosynthesis of a multipotent stilbene. Angew Chem Int Ed Engl. 2008;47(10):1942-5. doi: 10.1002/anie.200705148. [PubMed:18236486]
  2. Hu K, Webster JM: Antibiotic production in relation to bacterial growth and nematode development in Photorhabdus--Heterorhabditis infected Galleria mellonella larvae. FEMS Microbiol Lett. 2000 Aug 15;189(2):219-23. [PubMed:10930742]
External Links
ChemSpider
4943924
ChEMBL
CHEMBL259571
Wikipedia
3,5-Dihydroxy-4-isopropyl-trans-stilbene

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAtopic Dermatitis (AD)2
1CompletedTreatmentPsoriasis1
1WithdrawnTreatmentPsoriasis1
1, 2CompletedTreatmentAtopic Dermatitis (AD)1
2CompletedTreatmentAtopic Dermatitis (AD)2
2CompletedTreatmentPsoriasis2
3RecruitingTreatmentPsoriasis Vulgaris (Plaque Psoriasis)2
3WithdrawnTreatmentPsoriasis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0339 mg/mLALOGPS
logP4.25ALOGPS
logP4.95ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.19ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.67 m3·mol-1ChemAxon
Polarizability29.58 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Monocyclic monoterpenoids / Aromatic monoterpenoids / Phenylpropanes / Cumenes / Styrenes / Resorcinols / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Organooxygen compounds / Hydrocarbon derivatives
Substituents
Stilbene / P-cymene / Aromatic monoterpenoid / Monocyclic monoterpenoid / Monoterpenoid / Cumene / Phenylpropane / Resorcinol / Styrene / 1-hydroxy-4-unsubstituted benzenoid
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein heterodimerization activity
Specific Function
Cytokine that can act as a growth factor for activated T and NK cells, enhance the lytic activity of NK/lymphokine-activated killer cells, and stimulate the production of IFN-gamma by resting PBMC....
Gene Name
IL12B
Uniprot ID
P29460
Uniprot Name
Interleukin-12 subunit beta
Molecular Weight
37168.645 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Kinase activator activity
Specific Function
Produced by T-cells in response to antigenic or mitogenic stimulation, this protein is required for T-cell proliferation and other activities crucial to regulation of the immune response. Can stimu...
Gene Name
IL2
Uniprot ID
P60568
Uniprot Name
Interleukin-2
Molecular Weight
17627.52 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Interleukin-6 receptor binding
Specific Function
Cytokine with a wide variety of biological functions. It is a potent inducer of the acute phase response. Plays an essential role in the final differentiation of B-cells into Ig-secreting cells Inv...
Gene Name
IL6
Uniprot ID
P05231
Uniprot Name
Interleukin-6
Molecular Weight
23717.965 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Interleukin-8 receptor binding
Specific Function
IL-8 is a chemotactic factor that attracts neutrophils, basophils, and T-cells, but not monocytes. It is also involved in neutrophil activation. It is released from several cell types in response t...
Gene Name
CXCL8
Uniprot ID
P10145
Uniprot Name
Interleukin-8
Molecular Weight
11097.98 Da

Drug created on November 18, 2007 11:29 / Updated on June 04, 2019 06:21