Tapinarof

Tapinarof
Names
Trade namesVtama
Other namesBenvitimod; 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
Clinical data
Main usesPlaque psoriasis[1]
Side effectsFolliculitis, itchiness, contact dermatitis[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Routes of
use		Topical
Legal
License data
Legal status
Chemical and physical data
FormulaC17H18O2
Molar mass254.329 g·mol−1
3D model (JSmol)
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 to treat plaque psoriasis.[1][2] It is applied to the skin.[1]

Common side effects include folliculitis, itchiness, and contact dermatitis.[1] It is an aryl hydrocarbon receptor activator.[1]

Tapinarof was approved for medical use in the United States in 2022.[1] It is not approved in either Europe or the United Kingdom as of 2022.[3] In the United States 60 grams of 1% cream costs about 1,400 USD as of 2022.[4]

Medical uses

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

Dosage

It is applied as a 1% cream once per day.[1]

Society and culture

Names

Tapinarof is the International Nonproprietary Name (INN).[5]

Natural occurrence

Entomopathogenic nematodes emerging from a wax moth cadaver.

It is a naturally occurring compound found in bacterial symbionts of nematodes which has antibiotic properties.[6][7]

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.[6] 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.[7]

See also

  • Pinosylvin, a molecule produced in pines that does not bear the isopropyl alkylation.

References

  1. 1 2 3 4 5 6 7 8 9 10 "Vtama- tapinarof cream". DailyMed. 23 May 2022. Archived from the original on 3 July 2022. Retrieved 19 June 2022.
  2. ↑ Stein Gold, Linda; Rubenstein, David S.; Peist, Ken; Jain, Piyush; Tallman, Anna M. (September 2021). "Tapinarof cream 1% once daily and benvitimod 1% twice daily are 2 distinct topical medications". Journal of the American Academy of Dermatology. 85 (3): e201–e202. doi:10.1016/j.jaad.2021.04.103.
  3. ↑ "Tapinarof". SPS - Specialist Pharmacy Service. 29 August 2020. Archived from the original on 26 January 2022. Retrieved 12 December 2022.
  4. ↑ "Vtama Prices, Coupons, Copay & Patient Assistance". Drugs.com. Retrieved 12 December 2022.
  5. ↑ World Health Organization (2017). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 78". WHO Drug Information. 31 (3). hdl:10665/330961.
  6. 1 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.
  7. 1 2 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.
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