Tecovirimat

Tecovirimat
Clinical data
Trade namesTpoxx
Other namesST-246
AHFS/Drugs.comMonograph
License data
Routes of
administration
By mouth, intravenous
ATC code
Legal status
Legal status
Identifiers
  • N-{3,5-Dioxo-4-azatetracyclo[5.3.2.0{2,6}.0{8,10}]dodec-11-en-4- yl}-4-(trifluoromethyl)benzamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC19H15F3N2O3
Molar mass376.335 g·mol−1
3D model (JSmol)
  • FC(F)(F)c1ccc(cc1)C(=O)NN1C(=O)C2C(C3C=CC2C2CC32)C1=O
  • InChI=1S/C19H15F3N2O3/c20-19(21,22)9-3-1-8(2-4-9)16(25)23-24-17(26)14-10-5-6-11(13-7-12(10)13)15(14)18(24)27/h1-6,10-15H,7H2,(H,23,25) checkY
  • Key:CSKDFZIMJXRJGH-UHFFFAOYSA-N checkY

Tecovirimat, sold under the brand name Tpoxx among others,[6] is an antiviral medication with activity against orthopoxviruses such as smallpox and mpox.[4][7][8] In 2018 it became the first antipoxviral drug approved in the United States.[9][10]

The drug works by blocking cellular transmission of the virus, thus preventing the disease.[11] It is an inhibitor of the orthopoxvirus VP37 envelope wrapping protein.[4]

Tecovirimat has been effective in laboratory testing; it has been shown to protect animals from mpox and rabbitpox and causes no serious side effects in humans.[6] Tecovirimat was first used for treatment in December 2018, after a laboratory-acquired vaccinia virus infection.[12]

Two million doses of tecovirimat are stockpiled in the US Strategic National Stockpile should an orthopoxvirus-based bioterror attack occur.[13][14] The U.S. Food and Drug Administration (FDA) considers it to be a first-in-class medication.[15]

  1. ^ "Notice: Multiple Additions to the Prescription Drug List (PDL) [2022-01-24]". Health Canada. 24 January 2022. Archived from the original on 29 May 2022. Retrieved 28 May 2022.
  2. ^ "New Medicines Approved in 2018". Health Canada. 15 January 2020. Archived from the original on 29 May 2022. Retrieved 28 May 2022.
  3. ^ "Summary Basis of Decision (SBD) for Tpoxx". Health Canada. 23 October 2014. Archived from the original on 29 May 2022. Retrieved 29 May 2022.
  4. ^ a b c "Tpoxx- tecovirimat monohydrate capsule". DailyMed. 2 December 2021. Archived from the original on 23 April 2022. Retrieved 23 April 2022.
  5. ^ Cite error: The named reference Tecovirimat SIGA EPAR was invoked but never defined (see the help page).
  6. ^ a b McNeil Jr DG (13 July 2018). "Drug to Treat Smallpox Approved by F.D.A., a Move Against Bioterrorism". The New York Times. Archived from the original on 28 March 2019. Retrieved 16 July 2018.
  7. ^ Nakoune E, Olliaro P (May 2022). "Waking up to monkeypox". BMJ. 377: o1321. doi:10.1136/bmj.o1321. PMID 35613732. S2CID 249047112.
  8. ^ Adler H, Gould S, Hine P, Snell LB, Wong W, Houlihan CF, et al. (May 2022). "Clinical features and management of human monkeypox: a retrospective observational study in the UK". The Lancet. Infectious Diseases. 22 (8): 1153–1162. doi:10.1016/S1473-3099(22)00228-6. PMC 9300470. PMID 35623380. S2CID 249057804.
  9. ^ "FDA approves the first drug with an indication for treatment of smallpox". U.S. Food and Drug Administration (FDA) (Press release). 13 July 2018. Archived from the original on 23 April 2019. Retrieved 1 August 2018.
  10. ^ "U.S. Food and Drug Administration Approves Siga Technologies' Tpoxx (tecovirimat) for the Treatment of Smallpox". SIGA (Press release). Archived from the original on 21 September 2018. Retrieved 14 July 2018.
  11. ^ Grosenbach DW, Honeychurch K, Rose EA, Chinsangaram J, Frimm A, Maiti B, et al. (July 2018). "Oral Tecovirimat for the Treatment of Smallpox". The New England Journal of Medicine. 379 (1): 44–53. doi:10.1056/NEJMoa1705688. PMC 6086581. PMID 29972742.
  12. ^ Whitehouse ER, Rao AK, Yu YC, Yu PA, Griffin M, Gorman S, et al. (October 2019). "Novel Treatment of a Vaccinia Virus Infection from an Occupational Needlestick - San Diego, California, 2019" (PDF). MMWR. Morbidity and Mortality Weekly Report. 68 (42): 943–946. doi:10.15585/mmwr.mm6842a2. PMC 6812835. PMID 31647789. Archived (PDF) from the original on 2 August 2022. Retrieved 2 August 2022.
  13. ^ Damon IK, Damaso CR, McFadden G (May 2014). "Are we there yet? The smallpox research agenda using variola virus". PLOS Pathogens. 10 (5): e1004108. doi:10.1371/journal.ppat.1004108. PMC 4006926. PMID 24789223.
  14. ^ Cunningham A (13 July 2018). "FDA approves the first smallpox treatment". Archived from the original on 12 July 2018. Retrieved 4 May 2018.
  15. ^ New Drug Therapy Approvals 2018 (PDF). U.S. Food and Drug Administration (FDA) (Report). January 2019. Archived from the original on 17 September 2020. Retrieved 16 September 2020.

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