TAPINAROF

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 Search

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
Sources: https://clinicaltrials.gov/ct2/show/NCT03202004 | https://www.ncbi.nlm.nih.gov/pubmed/30612986 | https://www.gsk.com/en-gb/media/press-releases/roivant-subsidiary-dermavant-sciences-signs-agreement-with-gsk-to-purchase-rights-to-tapinarof/

Tapinarof (also known as benvitimod, WB-1001; GSK-2894512), an investigational therapeutic aryl hydrocarbon receptor modulating agent that selectively modulates the cytokine cascade deep under the skin, a process that rapidly decreases inflammations and skin plague. Tapinarof participated in clinical trials for the treatment of psoriasis and atopic dermatitis. Phase III clinical trials to evaluate the efficacy and safety of the cream for the topical treatment of plaque psoriasis (psoriasis) was terminated because of the business decision based on the need to prioritize and focus resources within GSK. In July 2018, Roivant subsidiary Dermavant Sciences purchased the rights for tapinarof. Besides, tapinarof participated in phase II clinical trials for patients with atopic dermatitis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Interferon gamma 1 Target ID: CHEMBL3286073 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24673513	Modulator 828
TNF-alpha 18 Target ID: CHEMBL1825 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24673513	Modulator 828
Interleukin-2 2 Target ID: CHEMBL2466 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24673513	Modulator 828

PubMed

Title	Date	PubMed
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	24673513
New therapies for atopic dermatitis: Additional treatment classes.	2018 Mar	29248520
Phase 2, randomized dose-finding study of tapinarof (GSK2894512 cream) for the treatment of plaque psoriasis.	2019 Mar	30612986

Sample Use Guides

In Vivo Use Guide

1 % (10 mg/g) GSK2894512 (BENVITIMOD) cream will be provided in tubes labeled in compliance with country requirements.

Route of Administration: Transdermal

Name

Type

Language

TAPINAROF

Official Name

English

3,5-DIHYDROXY-4-ISOPROPYL-TRANS-STILBENE

Systematic Name

English

VTAMA

Brand Name

English

tapinarof [INN]

Common 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