Chemical compound
Tapinarof , also known as benvitimod and sold under the brand name Vtama , is a
medication used for the treatment of
plaque psoriasis .
[1] The medication is
applied to the skin .
[1] Besides its use in medicine, tapinarof is a
naturally occurring compound found in
bacterial
symbionts of
nematodes which has
antibiotic properties.
[2]
[3]
The medication acts as an
aryl hydrocarbon receptor agonist.
[1]
[4]
Tapinarof was approved for medical use in the United States in May 2022.
[1]
[5]
[6]
[7] The US
Food and Drug Administration (FDA) considers it to be a
first-in-class medication .
[8]
[9]
Tapinarof is
indicated for the treatment of plaque psoriasis in adults.
[1]
In case of short term use the most common adverse effects are folliculitis, contact dermatitis, headache, pruritus (itching), and upper respiratory tract infection.
[10]
[11]
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.
[12]
[13]
[14]
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.
[10]
[15]
Tapinarof, also known as benvitimod and sold under the brand name Vtama, is a
medication used for the treatment of
plaque psoriasis .
[1] The medication is
applied to the skin .
[1] Besides its use in medicine, tapinarof is a
naturally occurring compound found in
bacterial
symbionts of
nematodes which has
antibiotic properties.
[2]
[3]
The medication acts as an
aryl hydrocarbon receptor agonist.
[1]
[4] Tapinarof was approved for medical use in the United States in May 2022.
[1]
[5]
[6]
[7] The US
Food and Drug Administration (FDA) considers it to be a
first-in-class medication .
[8]
Tapinarof is the
international nonproprietary name .
[16]
Entomopathogenic nematodes emerging from a wax moth cadaver.
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 .
[2] 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.
[3]
^
a
b
c
d
e
f
g
h
i
j
"Vtama- tapinarof cream" . DailyMed . 23 May 2022.
Archived from the original on 3 July 2022. Retrieved 19 June 2022 .
^
a
b
c Joyce SA, Brachmann AO, Glazer I, Lango L, Schwär G, Clarke DJ, et al. (2008). "Bacterial biosynthesis of a multipotent stilbene". Angewandte Chemie . 47 (10): 1942–1945.
CiteSeerX
10.1.1.603.247 .
doi :
10.1002/anie.200705148 .
PMID
18236486 .
^
a
b
c Hu K, Webster JM (August 2000).
"Antibiotic production in relation to bacterial growth and nematode development in Photorhabdus--Heterorhabditis infected Galleria mellonella larvae" . FEMS Microbiology Letters . 189 (2): 219–223.
doi :
10.1111/j.1574-6968.2000.tb09234.x .
PMID
10930742 .
^
a
b Bissonnette R, Stein Gold L, Rubenstein DS, Tallman AM, Armstrong A (April 2021).
"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.
doi :
10.1016/j.jaad.2020.10.085 .
PMID
33157177 .
^
a
b
"Vtama: FDA-Approved Drugs" . U.S.
Food and Drug Administration (FDA) .
Archived from the original on 25 May 2022. Retrieved 24 May 2022 .
^
a
b
"Vtama (Tapinarof) FDA Approval History" .
^
a
b
"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 (Press release). 24 May 2022.
Archived from the original on 24 May 2022. Retrieved 24 May 2022 .
^
a
b
"Advancing Health Through Innovation: New Drug Therapy Approvals 2022" . U.S.
Food and Drug Administration (FDA) . 10 January 2023. Retrieved 22 January 2023 . This article incorporates text from this source, which is in the
public domain .
^
New Drug Therapy Approvals 2022 (PDF) . U.S.
Food and Drug Administration (FDA) (Report). January 2024.
Archived from the original on 14 January 2024. Retrieved 14 January 2024 . This article incorporates text from this source, which is in the
public domain .
^
a
b Nogueira S, Rodrigues MA, Vender R, Torres T (December 2022).
"Tapinarof for the treatment of psoriasis" . Dermatologic Therapy . 35 (12): e15931.
doi :
10.1111/dth.15931 .
PMC
10078538 .
PMID
36226669 .
^ Lebwohl MG, Stein Gold L, Strober B, Papp KA, Armstrong AW, Bagel J, et al. (December 2021).
"Phase 3 Trials of Tapinarof Cream for Plaque Psoriasis" . The New England Journal of Medicine . 385 (24): 2219–2229.
doi :
10.1056/NEJMoa2103629 .
PMID
34879448 .
S2CID
245032475 .
^ Bissonnette R, Stein Gold L, Rubenstein DS, Tallman AM, Armstrong A (April 2021).
"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.
doi :
10.1016/j.jaad.2020.10.085 .
PMID
33157177 .
S2CID
226275222 .
^ Furue M, Hashimoto-Hachiya A, Tsuji G (October 2019).
"Aryl Hydrocarbon Receptor in Atopic Dermatitis and Psoriasis" . International Journal of Molecular Sciences . 20 (21): 5424.
doi :
10.3390/ijms20215424 .
PMC
6862295 .
PMID
31683543 .
^ Bissonnette R, Vasist LS, Bullman JN, Collingwood T, Chen G, Maeda-Chubachi T (June 2018). "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.
doi :
10.1002/cpdd.439 .
PMID
29389078 .
S2CID
23107777 .
^ Lebwohl MG, Stein Gold L, Strober B, Papp KA, Armstrong AW, Bagel J, et al. (December 2021).
"Phase 3 Trials of Tapinarof Cream for Plaque Psoriasis" . The New England Journal of Medicine . 385 (24): 2219–2229.
doi :
10.1056/NEJMoa2103629 .
PMID
34879448 .
^
World Health Organization (2017). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 78". WHO Drug Information . 31 (3).
hdl :
10665/330961 .
Dihydroxylated Trihydroxylated Tetrahydroxylated O-methylated
carboxylated other acylations
Glycosides
of resveratrol of rhapontigenin
Oligomeric forms
AhR Tooltip Aryl hydrocarbon receptor
Agonists:
Arachidonic acid
metabolites (e.g.,
lipoxin A4 ,
prostaglandin G2 )
Dietary carotenoids
Flutamide
Halogenated
aromatic hydrocarbons (e.g.,
polychlorinated dibenzodioxins (e.g.,
TCDD ),
dibenzofurans ,
biphenyls )
ΙΤΕ
Modified low-density lipoproteins
Polycyclic aromatic hydrocarbons (e.g.,
3-methylcholanthrene ,
benzo[a]pyrene ,
benzanthracenes ,
benzoflavones (e.g.,
β-naphthoflavone ))
Tapinarof (benvitimod)
Tetrapyroles (e.g.,
bilirubin )
Tryptophan
derivatives (e.g.,
indigo dye ,
indirubin )