Tapinarof

Tapinarof
Clinical data
Trade names	Vtama
Other names	Benvitimod; GSK-2894512; (E)-3,5-Dihydroxy-4-isopropyl-trans-stilbene; 3,5-Dihydroxy-4-isopropylstilbene
License data	US DailyMed: Tapinarof;
Routes of; administration	Topical
ATC code	None;
Legal status
Legal status	US: ℞-only [1];
Identifiers
	IUPAC name 5-[(E)-2-Phenylethen-1-yl]-2-(propan-2-yl)benzene-1,3-diol;
CAS Number	79338-84-4;
PubChem CID	6439522;
DrugBank	DB06083;
ChemSpider	4943924;
UNII	84HW7D0V04;
KEGG	D11365;
ChEMBL	ChEMBL259571;
Chemical and physical data
Formula	C17H18O2
Molar mass	254.329 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)c1c(cc(cc1O)/C=C/c2ccccc2)O;
	InChI 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+; Key: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.[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]

Medical uses

Tapinarof is indicated for the treatment of plaque psoriasis in adults.[1]

Society and culture

Names

Tapinarof is the International Nonproprietary Name (INN).[8]

Natural occurrence

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]

References

"Vtama- tapinarof cream". DailyMed. 23 May 2022. Archived from the original on 3 July 2022. Retrieved 19 June 2022.
Joyce SA, Brachmann AO, Glazer I, Lango L, Schwär G, Clarke DJ, Bode HB (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.
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.
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.
"Vtama: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 25 May 2022. Retrieved 24 May 2022.
"Vtama (Tapinarof) FDA Approval History".
"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.
World Health Organization (2017). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 78". WHO Drug Information. 31 (3). hdl:10665/330961.

External links

"Tapinarof". Drug Information Portal. U.S. National Library of Medicine.

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[Vtama_FDA_label-1] "Vtama- tapinarof cream". DailyMed. 23 May 2022. Archived from the original on 3 July 2022. Retrieved 19 June 2022.

[pmid18236486-2] Joyce SA, Brachmann AO, Glazer I, Lango L, Schwär G, Clarke DJ, Bode HB (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.

[pmid10930742-3] 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.

[4] 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.

[5] "Vtama: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 25 May 2022. Retrieved 24 May 2022.

[6] "Vtama (Tapinarof) FDA Approval History".

[7] "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.

[8] World Health Organization (2017). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 78". WHO Drug Information. 31 (3). hdl:10665/330961.