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Tapinarof AhR agonist

Name: Tapinarof
Brand: Selleck Chemicals
SKU: S9700
Availability: InStock
Rating: 5 (5 reviews)

Cat.No.S9700

Tapinarof (GSK2894512, Benvitimod, WBI 1001, DHPS, DMVT 505) is a natural agonist of aryl hydrocarbon receptor (AhR) and induces nuclear translocation of AhR in immortalized keratinocytes (HaCaT) with EC50 of 0.16 nM. This compound induces cellular apoptosis in CD4+ T cells in a dosedependent manner with IC50 of 5.2 μM.

Chemical Structure

Molecular Weight: 254.32

Jump to Mechanism of Action Solubility Chemical Information, Storage & Stability Specificity

Quality Control

Batch: S970001 DMSO]51 mg/mL]false]Ethanol]51 mg/mL]false]Water]Insoluble]false Purity: 99.98%

99.98

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Chemical Information, Storage & Stability

Molecular Weight	254.32	Formula	C₁₇H₁₈O₂	Storage (From the date of receipt)	3 years -20°C powder
CAS No.	79338-84-4	--		Storage of Stock Solutions	1 year-80°Cin solvent 1 month-20°Cin solvent
Synonyms	GSK2894512, Benvitimod, WBI 1001, DHPS, DMVT 505			Smiles	CC(C)C1=C(O)C=C(\C=C\C2=CC=CC=C2)C=C1O

Solubility

In vitro
Batch:

DMSO : 51 mg/mL (200.53 mM)
(Moisture-contaminated DMSO may reduce solubility. Use fresh, anhydrous DMSO.)

Ethanol : 51 mg/mL

Water : Insoluble

Molarity Calculator

Mass	Concentration	Volume	Molecular Weight
=	×	×

Dilution Calculator Molecular Weight Calculator

In vivo Batch:
Homogeneous suspension	CMC-NA	≥5mg/ml	Taking the 1 mL working solution as an example, add 5 mg of this product to 1 ml of CMC-Na solution, mix evenly to obtain a homogeneous suspension with a final concentration of 5 mg/ml.
Clear solution	5%DMSO 1 40%PEG300 2 5%Tween80 3 50%ddH2O Validated by Selleck labs. Should you need adjustments to this formulation, contact our sales team for custom testing.	2.500mg/ml (9.83mM)	Taking the 1 mL working solution as an example, add 50 μL of 50 mg/ml clarified DMSO stock solution to 400 μL of PEG300, mix evenly to clarify it; add 50 μL of Tween80 to the above system, mix evenly to clarify; then continue to add 500 μL of ddH2O to adjust the volume to 1 mL. The mixed solution should be used immediately for optimal results.
Clear solution	5% DMSO 1 95% Corn oil Validated by Selleck labs. Should you need adjustments to this formulation, contact our sales team for custom testing.	0.850mg/ml (3.34mM)	Taking the 1 mL working solution as an example, add 50 μL of 17 mg/ml clear DMSO stock solution to 950 μL of corn oil and mix evenly. The mixed solution should be used immediately for optimal results.

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)

Dosage: mg/kg Average weight of animals: g Dosing volume per animal:μL Number of animals:

Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)

% DMSO + % + % Tween 80 + % ddH₂O

%DMSO+ %

Calculation results:

Working concentration: mg/ml;

Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such
as vortex, ultrasound or hot water bath can be used to aid dissolving.

Mechanism of Action

Targets/IC₅₀/Ki	AhR ^[1] (in immortalized keratinocytes) 0.16 nM(EC50) apoptosis ^[1] (in CD4+ T cells) 5.2 μM
In vitro	Tapinarof binds and activates AhR in multiple cell types, including cells of the target tissue –human skin. In addition, this compound moderates proinflammatory cytokine expression in stimulated peripheral blood CD4+ T cells and ex vivo human skin, and impacts barrier gene expression in primary human keratinocytes; both of these processes are likely to be downstream of AhR activation based on current evidence.^[1]
In vivo	The anti-inflammatory properties of tapinarof derive from AhR agonism is conclusively demonstrated using the mouse model of imiquimod-induced psoriasiform skin lesions. Topical treatment of AhR-sufficient mice with this compound leads to compound-driven reductions in erythema, epidermal thickening and tissue cytokine levels. In contrast, this chemical has no impact on imiquimod-induced skin inflammation in AhR-deficient mice.^[1]
References	[1] https://pubmed.ncbi.nlm.nih.gov/28595996/

Clinical Trial Information

(data from https://clinicaltrials.gov, updated on 2024-05-22)

NCT Number	Recruitment	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT05979896	Recruiting	Malaria	Malaria Consortium	July 28 2023	Phase 4
NCT05478954	Active not recruiting	Malaria	Malaria Consortium	July 15 2022	Phase 4
NCT05471544	Active not recruiting	Malaria	Malaria Consortium	July 18 2022	Phase 3
NCT05326659	Unknown status	Psoriasis	Peking University People''s Hospital\|Zhonghao Pharmaceutical	April 2022	Not Applicable
NCT05326672	Unknown status	Atopic Dermatitis	Peking University People''s Hospital\|Zhonghao Pharmaceutical	April 2022	Phase 3
NCT05172726	Recruiting	Plaque Psoriasis	Dermavant Sciences Inc.	December 2 2021	Phase 3

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