Tapinarof, also known as benvitimod and sold under the brand name Vtama, is a

medication A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy (pharmacotherapy) is an important part of the medical field and re ...

used for the treatment of

plaque psoriasis Psoriasis is a long-lasting, noncontagious autoimmune disease characterized by raised areas of abnormal skin. These areas are red, pink, or purple, dry, itchy, and scaly. Psoriasis varies in severity from small, localized patches to complete ...

. The medication is applied to the skin. Besides its use in medicine, tapinarof is a

naturally occurring A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical sy ...

compound found in

bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among ...

symbiont Symbiosis (from Greek , , "living together", from , , "together", and , bíōsis, "living") is any type of a close and long-term biological interaction between two different biological organisms, be it mutualistic, commensalistic, or parasit ...

s of

nematode The nematodes ( or grc-gre, Νηματώδη; la, Nematoda) or roundworms constitute the phylum Nematoda (also called Nemathelminthes), with plant-Parasitism, parasitic nematodes also known as eelworms. They are a diverse animal phylum inhab ...

s which has

antibiotic An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of ...

properties. The medication acts as an

aryl hydrocarbon receptor The aryl hydrocarbon receptor (also known as AhR, AHR, ahr, ahR, or dioxin receptor) is a protein that in humans is encoded by the AHR gene. The aryl hydrocarbon receptor is a transcription factor that regulates gene expression. It was originall ...

agonist. Tapinarof was approved for medical use in the United States in May 2022.

Medical uses

Tapinarof is

indicated In medicine, an indication is a valid reason to use a certain test, medication, procedure, or surgery. There can be multiple indications to use a procedure or medication. An indication can commonly be confused with the term diagnosis. A diagnosis ...

for the treatment of plaque psoriasis in adults.

Society and culture

Names

Tapinarof is the International Nonproprietary Name (INN).

Natural occurrence

Tapinarof, also known as benvitimod, is a bacterial

stilbenoid Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Most stilbenoids are prod ...

produced in '' Photorhabdus'' bacterial symbionts of ''

Heterorhabditis ''Heterorhabditis'' is a genus of nematodes belonging to the order Rhabditida. All species of this genus are obligate parasites of insects, and some are used as biological control agents for the control of pest insects. ''Heterorhabditis'' nemat ...

'' nematodes. It is a product of an alternative

ketosynthase Ketoacyl synthases (KSs) catalyze the condensation reaction of acyl-CoA or acyl-acyl ACP with malonyl-CoA to form 3-ketoacyl-CoA or with malonyl-ACP to form 3-ketoacyl-ACP. This reaction is a key step in the fatty acid synthesis cycle, as the result ...

-directed stilbenoid biosynthesis pathway. It is derived from the

condensation Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapor to ...

of two β-ketoacyl

thioester In organic chemistry, thioesters are organosulfur compounds with the functional group . They are analogous to carboxylate esters () with the sulfur in the thioester playing the role of the linking oxygen in the carboxylate ester, as implied by t ...

s. It is produced by the '' Photorhabdus luminescens'' bacterial symbiont species of the entomopathogenic nematode, '' Heterorhabditis megidis''. Experiments with infected larvae of ''

Galleria mellonella ''Galleria mellonella'', the greater wax moth or honeycomb moth, is a moth of the family Pyralidae. ''G. mellonella'' is found throughout the world. It is one of two species of wax moths, with the other being the lesser wax moth. ''G. 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.

References

External links