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This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C17H18O2
Molecular Weight 254.3236
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of Tapinarof

SMILES

CC(C)C1=C(O)C=C(\C=C\C2=CC=CC=C2)C=C1O

InChI

InChIKey=ZISJNXNHJRQYJO-CMDGGOBGSA-N
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+

HIDE SMILES / InChI

Molecular Formula C17H18O2
Molecular Weight 254.3236
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Tapinarof (also known as benvitimod, WB-1001; GSK-2894512), a therapeutic aryl hydrocarbon receptor agonist that selectively modulates the cytokine cascade deep under the skin, a process that rapidly decreases inflammations and skin plague. Tapinarof cream 1% (VTAMA®) is being developed by Dermavant Sciences Inc. (a subsidiary of Roivant Sciences Inc.) as a once-daily topical treatment for plaque psoriasis and atopic dermatitis. In May 2022, tapinarof cream 1% was approved in the USA for the topical treatment of plaque psoriasis in adults. Tapinarof cream 1% is also being investigated for the treatment of atopic dermatitis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
100.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VTAMA

Approved Use

Indicated for the topical treatment of plaque psoriasis in adults.

Launch Date

2022
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
898 pg/mL
5.23 g 1 times / day multiple, topical
dose: 5.23 g
route of administration: Topical
experiment type: MULTIPLE
co-administered:
BENVITIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
116 pg/mL
5.23 g 1 times / day multiple, topical
dose: 5.23 g
route of administration: Topical
experiment type: MULTIPLE
co-administered:
BENVITIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4067 pg × h/mL
5.23 g 1 times / day multiple, topical
dose: 5.23 g
route of administration: Topical
experiment type: MULTIPLE
co-administered:
BENVITIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
608.6 pg × h/mL
5.23 g 1 times / day multiple, topical
dose: 5.23 g
route of administration: Topical
experiment type: MULTIPLE
co-administered:
BENVITIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.41 h
5.23 g 1 times / day multiple, topical
dose: 5.23 g
route of administration: Topical
experiment type: MULTIPLE
co-administered:
BENVITIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.6%
BENVITIMOD plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Disc. AE: Contact dermatitis, Folliculitis...
AEs leading to
discontinuation/dose reduction:
Contact dermatitis (2.6%)
Folliculitis (2.2%)
Psoriasis (1%)
Drug eruption (0.5%)
Nasopharyngitis (0.4%)
Motor vehicle accident (0.4%)
Pruritus (0.3%)
Squamous cell cancer (0.3%)
Urticaria (0.1%)
Stasis dermatitis (0.1%)
Abscess neck (0.1%)
Pancreatitis (0.1%)
Esophagitis (0.1%)
Facial bone fracture (0.1%)
Sources:
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Disc. AE: Psoriasis exacerbation, Ankle/tibial fractures...
Other AEs: Adverse event, Contact dermatitis...
AEs leading to
discontinuation/dose reduction:
Psoriasis exacerbation (0.7%)
Ankle/tibial fractures (0.1%)
Other AEs:
Adverse event (6%)
Contact dermatitis (2%)
Headache (0.7%)
Application site reaction (0.6%)
Vascular disease (0.4%)
Musculoskeletal pain (0.3%)
Urticaria (0.1%)
Asteatosis (0.1%)
Cholelithiasis (0.1%)
Hypertension (0.1%)
Impetigo (0.1%)
Stab wound (0.1%)
Sunburn (0.1%)
Transaminitis (0.1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Abscess neck 0.1%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Esophagitis 0.1%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Facial bone fracture 0.1%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Pancreatitis 0.1%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Stasis dermatitis 0.1%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Urticaria 0.1%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Pruritus 0.3%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Squamous cell cancer 0.3%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Motor vehicle accident 0.4%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Nasopharyngitis 0.4%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Drug eruption 0.5%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Psoriasis 1%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Folliculitis 2.2%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Contact dermatitis 2.6%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
Asteatosis 0.1%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Cholelithiasis 0.1%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Hypertension 0.1%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Impetigo 0.1%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Stab wound 0.1%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Sunburn 0.1%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Transaminitis 0.1%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Urticaria 0.1%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Ankle/tibial fractures 0.1%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Musculoskeletal pain 0.3%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Vascular disease 0.4%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Application site reaction 0.6%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Headache 0.7%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Psoriasis exacerbation 0.7%
Disc. AE
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Contact dermatitis 2%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Adverse event 6%
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >0.1 uM]
no [Inhibition 0.1 uM]
no
no
no
no
no
no
no
no
no
no
yes [EC50 0.0002 uM]
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
major
major
major
minor
minor
minor
minor
no
no
no
no
Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed

Sample Use Guides

1 % (10 mg/g) cream: apply a thin layer of VTAMA cream to affected areas once daily.
Route of Administration: Topical
In Vitro Use Guide
Tapinarof dose-dependently induced nuclear translocation of AhR in immortalized keratinocytes (HaCaT) (EC50 = 0.16 nM). Human keratinocytes exposed to 0.1 and 1.0 mM tapinarof for 3 days induced CYP1A1 expression without marked cell death. Tapinarof induced cellular apoptosis in CD4 T cells in a dose-dependent manner (IC50=5.2 uM)
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:15:49 GMT 2025
Edited
by admin
on Mon Mar 31 21:15:49 GMT 2025
Record UNII
84HW7D0V04
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Tapinarof
INN  
INN  
Official Name English
Tapinarof [INN]
Preferred Name English
3,5-Dihydroxy-4-isopropyl-trans-stilbene
Systematic Name English
VTAMA
Brand Name English
1,3-Benzenediol, 2-(1-methylethyl)-5-(2-phenylethenyl)-, (E)-
Systematic Name English
(E)-2-(1-Methylethyl)-5-(2-phenylethenyl)-1,3-benzenediol
Systematic Name English
5-[(1E)-2-Phenylethen-1-yl]-2-(propan-2-yl)benzene-1,3-diol
Systematic Name English
2-(1-Methylethyl)-5-[(1E)-2-phenylethenyl]-1,3-benzenediol
Systematic Name English
GSK2894512
Code English
BENVITIMOD
Common Name English
3,5-Dihydroxy-4-isopropylstilbene
Systematic Name English
Tapinarof [WHO-DD]
Common Name English
WBI-1001
Code English
GSK-2894512
Code English
Tapinarof [USAN]
Common Name English
1,3-Benzenediol, 2-(1-methylethyl)-5-[(1E)-2-phenylethenyl]-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
Code System Code Type Description
RXCUI
2602286
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
PRIMARY
PUBCHEM
6439522
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
PRIMARY
EPA CompTox
DTXSID301045262
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
PRIMARY
CAS
79338-84-4
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
PRIMARY
INN
10253
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
PRIMARY
WIKIPEDIA
Benvitimod
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
PRIMARY
NCI_THESAURUS
C152511
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
PRIMARY
CAS
115781-08-3
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY
USAN
EF-83
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
PRIMARY
SMS_ID
100000174276
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
PRIMARY
FDA UNII
84HW7D0V04
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
PRIMARY
DRUG BANK
DB06083
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
PRIMARY
DAILYMED
84HW7D0V04
Created by admin on Mon Mar 31 21:15:49 GMT 2025 , Edited by admin on Mon Mar 31 21:15:49 GMT 2025
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
EC50
OFF-TARGET->INHIBITOR
IC50
METABOLIC ENZYME -> SUBSTRATE
Low systematic exposure
BINDER->LIGAND
BINDING
TARGET -> AGONIST
Dose dependently induced nuclear translocation of AhR in immortalized keratinocytes (HaCaT cells) (half excitatory concentration.
EC50
Related Record Type Details
ACTIVE MOIETY