Tapinarof Explained

Tradename:Vtama
Dailymedid:Tapinarof
Routes Of Administration:Topical
Atc Prefix:D05
Atc Suffix:AX07
Class:Aryl hydrocarbon receptor agonist
Legal Us:Rx-only
Legal Us Comment:[1]
Cas Number:79338-84-4
Pubchem:6439522
Drugbank:DB06083
Chemspiderid:4943924
Unii:84HW7D0V04
Kegg:D11365
Chembl:259571
Synonyms:Benvitimod; GSK-2894512; (E)-3,5-Dihydroxy-4-isopropyl-trans-stilbene; 3,5-Dihydroxy-4-isopropylstilbene
Iupac Name:5-[(''E'')-2-Phenylethen-1-yl]-2-(propan-2-yl)benzene-1,3-diol
C:17
H:18
O:2
Smiles:CC(C)c1c(cc(cc1O)/C=C/c2ccccc2)O
Stdinchi: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+
Stdinchikey:ZISJNXNHJRQYJO-CMDGGOBGSA-N

Tapinarof, also known as benvitimod and sold under the brand name Vtama, is a medication used for the treatment of plaque psoriasis. The medication is applied to the skin. Besides its use in medicine, tapinarof is a naturally occurring compound found in bacterial symbionts of nematodes which has antibiotic properties.

The medication acts as an aryl hydrocarbon receptor agonist.[2]

Tapinarof was approved for medical use in the United States in May 2022.[3] [4] [5] The US Food and Drug Administration (FDA) considers it to be a first-in-class medication.[6] [7]

Medical uses

Tapinarof is indicated for the treatment of plaque psoriasis in adults.

Side effects

In case of short term use the most common adverse effects are folliculitis, contact dermatitis, headache, pruritus (itching), and upper respiratory tract infection.[8] [9]

Pharmacology

Mechanism of action

Tapinarof binds directly to topical aryl hydrocarbon receptor (AhR), suppressing inflammatory cytokines, modulating skin barrier protein expression, reducing oxidative stress, and regulating gene expression in immune cells.[10] [11] [12]

Efficacy

Tapinarof 1% cream once daily was superior to vehicle control in reducing the severity of plaque psoriasis over a period of 12 weeks and having a favorable safety profile in the treatment of psoriatic patients.[13]

History

Tapinarof, also known as benvitimod and sold under the brand name Vtama, is a medication used for the treatment of plaque psoriasis. The medication is applied to the skin. Besides its use in medicine, tapinarof is a naturally occurring compound found in bacterial symbionts of nematodes which has antibiotic properties.

The medication acts as an aryl hydrocarbon receptor agonist.[2] Tapinarof was approved for medical use in the United States in May 2022.[3] [4] [5] The US Food and Drug Administration (FDA) considers it to be a first-in-class medication.

Society and culture

Names

Tapinarof is the international nonproprietary name.[14]

Natural occurrence

Tapinarof, also known as benvitimod, is a bacterial stilbenoid produced in Photorhabdus bacterial symbionts of Heterorhabditis nematodes. It is a product of an alternative ketosynthase-directed stilbenoid biosynthesis pathway. It is derived from the condensation of two β-ketoacyl thioesters.[15] It is produced by the Photorhabdus luminescens bacterial symbiont species of the entomopathogenic nematode, Heterorhabditis megidis. Experiments with infected larvae of Galleria mellonella, the wax moth, support the hypothesis that the compound has antibiotic properties that help minimize competition from other microorganisms and prevents the putrefaction of the nematode-infected insect cadaver.[16]

Notes and References

  1. Web site: Vtama- tapinarof cream . DailyMed . 23 May 2022 . 19 June 2022 . 3 July 2022 . https://web.archive.org/web/20220703054146/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9309d20f-8cd4-4c96-93fa-7f730e83c7ab . live .
  2. 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 . Journal of the American Academy of Dermatology . 84 . 4 . 1059–1067 . April 2021 . 33157177 . 10.1016/j.jaad.2020.10.085 . doi . free .
  3. Web site: Vtama: FDA-Approved Drugs . U.S. Food and Drug Administration (FDA) . 24 May 2022 . 25 May 2022 . https://web.archive.org/web/20220525070132/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=215272 . live .
  4. Web site: Vtama (Tapinarof) FDA Approval History .
  5. FDA Approves Dermavant's Vtama (tapinarof) cream, 1% for the Treatment of Plaque Psoriasis in Adults: First Topical Novel Chemical Entity Launched for Psoriasis in the U.S. in 25 Years . Dermavant Sciences . 24 May 2022 . 24 May 2022 . 24 May 2022 . https://web.archive.org/web/20220524211841/https://www.dermavant.com/u-s-fda-approves-our-novel-topical-treatment-for-adults-with-plaque-psoriasis/ . live .
  6. Web site: Advancing Health Through Innovation: New Drug Therapy Approvals 2022 . U.S. Food and Drug Administration (FDA) . 10 January 2023 . 22 January 2023.
  7. New Drug Therapy Approvals 2022 . U.S. Food and Drug Administration (FDA) . January 2024 . PDF . 14 January 2024 . https://web.archive.org/web/20240114065648/https://www.fda.gov/media/164429/download . 14 January 2024 . live .
  8. Nogueira S, Rodrigues MA, Vender R, Torres T . Tapinarof for the treatment of psoriasis . Dermatologic Therapy . 35 . 12 . e15931 . December 2022 . 36226669 . 10078538 . 10.1111/dth.15931 .
  9. 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 . The New England Journal of Medicine . 385 . 24 . 2219–2229 . December 2021 . 34879448 . 10.1056/NEJMoa2103629 . 245032475 . free .
  10. 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 . Journal of the American Academy of Dermatology . 84 . 4 . 1059–1067 . April 2021 . 33157177 . 10.1016/j.jaad.2020.10.085 . 226275222 . free .
  11. Furue M, Hashimoto-Hachiya A, Tsuji G . Aryl Hydrocarbon Receptor in Atopic Dermatitis and Psoriasis . International Journal of Molecular Sciences . 20 . 21 . 5424 . October 2019 . 31683543 . 6862295 . 10.3390/ijms20215424 . free .
  12. Bissonnette R, Vasist LS, Bullman JN, Collingwood T, Chen G, Maeda-Chubachi T . Systemic Pharmacokinetics, Safety, and Preliminary Efficacy of Topical AhR Agonist Tapinarof: Results of a Phase 1 Study . Clinical Pharmacology in Drug Development . 7 . 5 . 524–531 . June 2018 . 29389078 . 10.1002/cpdd.439 . 23107777 .
  13. 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 . The New England Journal of Medicine . 385 . 24 . 2219–2229 . December 2021 . 34879448 . 10.1056/NEJMoa2103629 . free .
  14. ((World Health Organization)) . 2017 . International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 78 . WHO Drug Information . 31 . 3 . 10665/330961 . free . World Health Organization .
  15. Joyce SA, Brachmann AO, Glazer I, Lango L, Schwär G, Clarke DJ, Bode HB . Bacterial biosynthesis of a multipotent stilbene . Angewandte Chemie . 47 . 10 . 1942–1945 . 2008 . 18236486 . 10.1002/anie.200705148 . 10.1.1.603.247 .
  16. Hu K, Webster JM . Antibiotic production in relation to bacterial growth and nematode development in Photorhabdus--Heterorhabditis infected Galleria mellonella larvae . FEMS Microbiology Letters . 189 . 2 . 219–223 . August 2000 . 10930742 . 10.1111/j.1574-6968.2000.tb09234.x . free .

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