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MedKoo Cat#: 326981 | Name: Benvitimod
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Description:

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

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
Benvitimod
CAS#79338-84-4

Theoretical Analysis

MedKoo Cat#: 326981

Name: Benvitimod

CAS#: 79338-84-4

Chemical Formula: C17H18O2

Exact Mass: 254.1307

Molecular Weight: 254.33

Elemental Analysis: C, 80.28; H, 7.13; O, 12.58

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
250mg USD 650.00 2 Weeks
1g USD 1,250.00 2 Weeks
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Related CAS #
No Data
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
View handling instruction
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
Solvent mg/mL mM
Solubility
DMSO 88.0 346.01
Ethanol 51.0 200.53
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

Recalculate based on batch purity %
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.
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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