U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
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

Description

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.

Originator

Approval Year

2022
324
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 100.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
VTAMA

Approved Use

Indicated for the topical treatment of plaque psoriasis in adults.

Launch Date

2022
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
898 pg/mL
OTHER GOV'T
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf#page=61 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2022/215272s000lbl.pdf#page=5
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
OTHER GOV'T
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf#page=61 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2022/215272s000lbl.pdf#page=5
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
OTHER GOV'T
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf#page=61 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2022/215272s000lbl.pdf#page=5
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
OTHER GOV'T
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf#page=61 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2022/215272s000lbl.pdf#page=5
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
OTHER GOV'T
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf#page=61 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2022/215272s000lbl.pdf#page=5
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%
OTHER GOV'T
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf#page=35
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
1 % 1 times / day multiple, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/215272Orig1s000MultidisciplineR.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946
substrate
1193
substrate
1388
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT3
747

OCT2
779

MATE1
415

MATE2-K
77

BCRP
910

CYP
110

BSEP
550

P-gp
1741

OATP1B1
1079

OATP1B3
961

OAT1
725

OCT1
620
P-gp
2052

OATP1B3
435

CYP2C19
1119

UGT1A9
423

CYP1A2
1197

BCRP
697

CYP1A1
389

CYP1B1
104

OATP1B1
503
AhR
1

CYP1A2
832

CYP1A1
151
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP
150
 no [IC50 >0.1 uM]
BCRP
985
 no [Inhibition 0.1 uM]
BSEP
554
 no
MATE1
416
 no
MATE2-K
77
 no
OAT1
730
 no
OAT3
749
 no
OATP1B1
1095
 no
OATP1B3
970
 no
OCT1
656
 no
OCT2
782
 no
P-gp
1932
 no
AhR
1
 yes [EC50 0.0002 uM]
CYP1A1
272
 yes
CYP1A2
2333
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A1
389
 major
CYP1A2
1197
 major
CYP3A4
1946
 major
UGT1A9
423
 major
CYP1B1
104
 minor
CYP2C19
1119
 minor
CYP2C9
1193
 minor
CYP2D6
1388
 minor
BCRP
697
 no
OATP1B1
503
 no
OATP1B3
435
 no
P-gp
2052
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Randomized, double-blind, placebo-controlled, multiple-dose study of the safety, tolerability and pharmacokinetics of benvitimod, a candidate drug for the treatment of psoriasis.
2014 Aug
New therapies for atopic dermatitis: Additional treatment classes.
2018 Mar
Phase 2, randomized dose-finding study of tapinarof (GSK2894512 cream) for the treatment of plaque psoriasis.
2019 Mar

Sample Use Guides

In Vivo Use Guide
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)
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
ACTIVE MOIETY
Structure of Tapinarof
NIH
NCATS
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