Benvitimod | tapinarof | WB-1001 | WBI-1001 | GSK-2894512 | CAS#79338-84-4

Benvitimod
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 326981

CAS#: 79338-84-4

Description: Benvitimod, also known as tapinarof, WB-1001; GSK-2894512 and WBI-1001, is a non-steroidal anti-inflammatory drug (NSAID) potentially for the treatment of atopic dermatitis. WBI-1001 is an efficacious novel topical anti-inflammatory molecule for the treatment of AD.

Chemical Structure

Benvitimod

CAS# 79338-84-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326981
Name: Benvitimod
CAS#: 79338-84-4
Chemical Formula: C17H18O2
Exact Mass: 254.13
Molecular Weight: 254.329
Elemental Analysis: C, 80.28; H, 7.13; O, 12.58

Price and Availability

Size	Price	Availability
50mg	USD 550	2 Weeks
100mg	USD 950	2 Weeks
200mg	USD 1650	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Benvitimod; WB-1001; WBI-1001; WB1001; WBI 1001. GSK-2894512; GSK 2894512; GSK2894512; 3,5-DH4IS; tapinarof

IUPAC/Chemical Name: 3,5-Dihydroxy-4-isopropylstilbene

InChi Key: ZISJNXNHJRQYJO-CMDGGOBGSA-N

InChi Code: 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+

SMILES Code: CC(C1=C(O)C=C(C=C1O)/C=C/C2=CC=CC=C2)C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Tapinarof (WBI-1001) is a natural aryl hydrocarbon receptor (AhR) agonist with an EC50 of 13 nM.
In vitro activity:	At <1 μM, tapinarof was antiproliferative to B cells, coronary smooth muscle cells, and endothelial cells (Figure 2a; gray arrows). Furthermore, tapinarof induced tissue factor (CD142), E-selectin, IL-8, IL-1α, and sIgG and decreased eotaxin 3, sTNFα, sIL-10, sIL-6 (Figure 2a). Tapinarof also induced cellular apoptosis in CD4+ T cells in a dose-dependent manner (IC50 = 5.2 μM). Reference: J Invest Dermatol. 2017 Oct;137(10):2110-2119. https://www.jidonline.org/article/S0022-202X(17)31543-9/fulltext
In vivo activity:	Mice treated topically with tapinarof showed significantly less inflammation, epidermal thickening, and proinflammatory cytokine expression than mice treated for 10 days with vehicle alone (Figure 4a–c). Decreased tissue cytokine expression was observed in tapinarof-treated mice, including Il17a, Il17f, Il19, Il22, Il23a, and Il1β, which were dose-dependently inhibited by tapinarof (Figure 4d, Supplementary Table S4 online). Interestingly, this activity was restricted to select biomarkers, as IMQ-induced expression of other cytokines was either not affected (Il6) or increased (Il10 and IP10) by tapinarof (Supplementary Table S4). Reference: J Invest Dermatol. 2017 Oct;137(10):2110-2119. https://www.jidonline.org/article/S0022-202X(17)31543-9/fulltext

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	88.0	346.01
	Ethanol	51.0	200.53

Preparing Stock Solutions

The following data is based on the product molecular weight 254.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Smith SH, Jayawickreme C, Rickard DJ, Nicodeme E, Bui T, Simmons C, Coquery CM, Neil J, Pryor WM, Mayhew D, Rajpal DK, Creech K, Furst S, Lee J, Wu D, Rastinejad F, Willson TM, Viviani F, Morris DC, Moore JT, Cote-Sierra J. Tapinarof Is a Natural AhR Agonist that Resolves Skin Inflammation in Mice and Humans. J Invest Dermatol. 2017 Oct;137(10):2110-2119. doi: 10.1016/j.jid.2017.05.004. Epub 2017 Jun 6. PMID: 28595996.
In vitro protocol:	1. Smith SH, Jayawickreme C, Rickard DJ, Nicodeme E, Bui T, Simmons C, Coquery CM, Neil J, Pryor WM, Mayhew D, Rajpal DK, Creech K, Furst S, Lee J, Wu D, Rastinejad F, Willson TM, Viviani F, Morris DC, Moore JT, Cote-Sierra J. Tapinarof Is a Natural AhR Agonist that Resolves Skin Inflammation in Mice and Humans. J Invest Dermatol. 2017 Oct;137(10):2110-2119. doi: 10.1016/j.jid.2017.05.004. Epub 2017 Jun 6. PMID: 28595996.
In vivo protocol:	1. Smith SH, Jayawickreme C, Rickard DJ, Nicodeme E, Bui T, Simmons C, Coquery CM, Neil J, Pryor WM, Mayhew D, Rajpal DK, Creech K, Furst S, Lee J, Wu D, Rastinejad F, Willson TM, Viviani F, Morris DC, Moore JT, Cote-Sierra J. Tapinarof Is a Natural AhR Agonist that Resolves Skin Inflammation in Mice and Humans. J Invest Dermatol. 2017 Oct;137(10):2110-2119. doi: 10.1016/j.jid.2017.05.004. Epub 2017 Jun 6. PMID: 28595996.

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1: Lu ST, Kelly KA, Feldman SR. An overview of benvitimod for the treatment of psoriasis: a narrative review. Expert Opin Pharmacother. 2022 Feb;23(3):327-333. doi: 10.1080/14656566.2021.2016699. Epub 2021 Dec 31. PMID: 34937468.

2: Ehsan M, Rehman AU, Athar F, Mustafa B, Javed H, Cheema HA, Ayyan M, Shahid A, Jafar U, Goldust M. Benvitimod for the treatment of psoriasis: A systematic review and meta-analysis of randomized controlled trials. Dermatol Ther. 2022 Dec;35(12):e15957. doi: 10.1111/dth.15957. Epub 2022 Nov 1. PMID: 36279313.

3: Puar N, Chovatiya R, Paller AS. New treatments in atopic dermatitis. Ann Allergy Asthma Immunol. 2021 Jan;126(1):21-31. doi: 10.1016/j.anai.2020.08.016. Epub 2020 Aug 17. PMID: 32818591.

4: Cai L, Chen GH, Lu QJ, Zheng M, Li YZ, Chen J, Zheng J, Zhang FR, Yu JB, Yang S, Li FQ, Xiao SX, Sun QN, Xu JH, Gao XH, Fang H, Gao TW, Hao F, Liu QZ, Tu YT, Li RY, Wang BX, Deng DQ, Zheng QS, Liu HX, Zhang JZ. A double-blind, randomized, placebo- and positive-controlled phase III trial of 1% benvitimod cream in mild- to-moderate plaque psoriasis. Chin Med J (Engl). 2020 Nov 9;133(24):2905-2909. doi: 10.1097/CM9.0000000000001221. PMID: 33177393; PMCID: PMC7752683.

5: Lebwohl MG, Stein Gold L, Strober B, Papp KA, Armstrong AW, Bagel J, Kircik L, Ehst B, Hong HC, Soung J, Fromowitz J, Guenthner S, Piscitelli SC, Rubenstein DS, Brown PM, Tallman AM, Bissonnette R. Phase 3 Trials of Tapinarof Cream for Plaque Psoriasis. N Engl J Med. 2021 Dec 9;385(24):2219-2229. doi: 10.1056/NEJMoa2103629. PMID: 34879448.

6: Lé AM, Torres T. New Topical Therapies for Psoriasis. Am J Clin Dermatol. 2022 Jan;23(1):13-24. doi: 10.1007/s40257-021-00649-w. Epub 2021 Oct 27. Erratum in: Am J Clin Dermatol. 2021 Dec 14;: PMID: 34705167.

7: Furue M, Hashimoto-Hachiya A, Tsuji G. Aryl Hydrocarbon Receptor in Atopic Dermatitis and Psoriasis. Int J Mol Sci. 2019 Oct 31;20(21):5424. doi: 10.3390/ijms20215424. PMID: 31683543; PMCID: PMC6862295.

8: Kleinman E, Laborada J, Metterle L, Eichenfield LF. What's New in Topicals for Atopic Dermatitis? Am J Clin Dermatol. 2022 Sep;23(5):595-603. doi: 10.1007/s40257-022-00712-0. Epub 2022 Sep 1. PMID: 36048410; PMCID: PMC9464760.

9: Bissonnette R, Stein Gold L, Rubenstein DS, Tallman AM, Armstrong A. Tapinarof in the treatment of psoriasis: A review of the unique mechanism of action of a novel therapeutic aryl hydrocarbon receptor-modulating agent. J Am Acad Dermatol. 2021 Apr;84(4):1059-1067. doi: 10.1016/j.jaad.2020.10.085. Epub 2020 Nov 3. PMID: 33157177.

10: Keam SJ. Tapinarof Cream 1%: First Approval. Drugs. 2022 Jul;82(11):1221-1228. doi: 10.1007/s40265-022-01748-6. Erratum in: Drugs. 2022 Aug 17;: Erratum in: Drugs. 2022 Sep;82(13):1433. PMID: 35939180; PMCID: PMC9427914.

11: Fernández-Gallego N, Sánchez-Madrid F, Cibrian D. Role of AHR Ligands in Skin Homeostasis and Cutaneous Inflammation. Cells. 2021 Nov 15;10(11):3176. doi: 10.3390/cells10113176. PMID: 34831399; PMCID: PMC8622815.

12: Nogueira S, Rodrigues MA, Vender R, Torres T. Tapinarof for the treatment of psoriasis. Dermatol Ther. 2022 Dec;35(12):e15931. doi: 10.1111/dth.15931. Epub 2022 Oct 21. PMID: 36226669; PMCID: PMC10078538.

13: Cai Z, Zeng Y, Shi X, Zhang X, Zhu H, Wang W. Benvitimod inhibits MCM6-meditated proliferation of keratinocytes by regulating the JAK/STAT3 pathway. J Dermatol Sci. 2023 Feb;109(2):71-79. doi: 10.1016/j.jdermsci.2023.01.010. Epub 2023 Jan 29. PMID: 36774328.

14: Yamamura K, Nakahara T. The Dawn of a New Era in Atopic Dermatitis Treatment. J Clin Med. 2022 Oct 18;11(20):6145. doi: 10.3390/jcm11206145. PMID: 36294465; PMCID: PMC9605067.

15: Freitas E, Gooderham M, Torres T. New Topical Therapies in Development for Atopic Dermatitis. Drugs. 2022 Jun;82(8):843-853. doi: 10.1007/s40265-022-01722-2. Epub 2022 May 21. PMID: 35596877.

16: Zhang J, Cai L, Zheng M. A novel topical treatment for plaque psoriasis: Benvitimod/tapinarof. J Am Acad Dermatol. 2022 Mar;86(3):e137-e138. doi: 10.1016/j.jaad.2021.10.053. Epub 2021 Nov 3. PMID: 34742862.

17: Tracy A, Bhatti S, Eichenfield LF. Update on pediatric atopic dermatitis. Cutis. 2020 Sep;106(3):143-146. doi: 10.12788/cutis.0077. PMID: 33104117.

18: Furue M. Regulation of Filaggrin, Loricrin, and Involucrin by IL-4, IL-13, IL-17A, IL-22, AHR, and NRF2: Pathogenic Implications in Atopic Dermatitis. Int J Mol Sci. 2020 Jul 29;21(15):5382. doi: 10.3390/ijms21155382. PMID: 32751111; PMCID: PMC7432778.

19: Wang X, Wang H, Wu X, Lu Y. Characterization and determination of benvitimod, an unknown risk substance in cosmetics, using nuclear magnetic resonance spectroscopy and HPLC-MS/MS. J Sep Sci. 2022 Oct;45(19):3652-3662. doi: 10.1002/jssc.202200388. Epub 2022 Aug 2. PMID: 35822938.

20: Chen L, Wu Y, Xiao B, Gao X, Sun Y. Application of benvitimod on psoriasis: A systematic review and meta-analysis of randomized controlled trials. A systematic review of benvitimod on psoriasis. Therapie. 2022 May- Jun;77(3):339-347. doi: 10.1016/j.therap.2021.09.005. Epub 2021 Oct 2. PMID: 34689959.

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