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Tecovirimat

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Tecovirimat
Clinical data
Trade namesTpoxx
Other namesST-246
Routes of
administration		By mouth
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
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 (ST-246 or Tpoxx)[2] is an antiviral with activity against orthopoxviruses such as smallpox and monkeypox. It is the only antipoxviral drug approved in the United States.[3]

The drug works by blocking cellular transmission of the virus, thus preventing the disease.[4] Tecovirimat has been effective in laboratory testing; it has been shown to protect animals from monkeypox and rabbitpox and causes no serious side effects in humans.[2] However, tecovirimat has never been used to treat a human with smallpox due to the disease's eradication.

Two million doses of tecovirimat are stockpiled in the US Strategic National Stockpile should an orthopoxvirus-based bioterror attack occur.[5][6]

Clinical study

The results of clinical trials involving tecovirimat supports its use against smallpox and other related orthopoxviruses. It has shown potential for a variety of uses including preventive healthcare, as a post-exposure therapeutic, as a therapeutic and an adjunct to vaccination.[7]

Tecovirimat can be taken orally and has recently been granted permission to conduct Phase II trials by the U.S. Food and Drug Administration (FDA). In Phase I trials tecovirimat was generally well tolerated with no serious adverse events.[8] Due to its importance for biodefense, the FDA has designated tecovirimat for 'fast-track' status, creating a path for expedited FDA review and eventual regulatory approval. On 13 July 2018, the FDA announced approval of tecovirimat.[9]

Mechanism of action

Tecovirimat inhibits the function of a major envelope protein required for the production of extracellar virus. Thus the virus is prevented from leaving an infected cell and the spread of the virus within the body is prevented.[10]

Society and culture

Originally researched by the National Institute of Allergy and Infectious Diseases, the drug was previously owned by Viropharma and discovered in collaboration with scientists at USAMRIID. It is currently[when?] owned and manufactured by Siga Technologies, a pharmaceutical company in the biodefense arena that won a government contract to develop the drug.

References

  1. ^ "U.S. Food and Drug Administration Approves SIGA Technologies' TPOXX (tecovirimat) for the Treatment of Smallpox - SIGA". SIGA.
  2. ^ a b McNeil Jr., Donald G. "Drug to Treat Smallpox Approved by F.D.A., a Move Against Bioterrorism". The New York Times. Retrieved 16 July 2018. {{cite web}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  3. ^ "FDA approves the first drug with an indication for treatment of smallpox". U.S. Food and Drug Administration (FDA) (Press release). Retrieved 1 August 2018.
  4. ^ 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.
  5. ^ 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  6. ^ Cunningham, Aimee (13 July 2018). "FDA approves the first smallpox treatment". {{cite web}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  7. ^ Siga Technologies
  8. ^ Jordan R, Tien D, Bolken TC, Jones KF, Tyavanagimatt SR, Strasser J, et al. (May 2008). "Single-dose safety and pharmacokinetics of ST-246, a novel orthopoxvirus egress inhibitor". Antimicrobial Agents and Chemotherapy. 52 (5): 1721–7. doi:10.1128/AAC.01303-07. PMC 2346641. PMID 18316519.
  9. ^ Commissioner, Office of the. "Press Announcements - FDA approves the first drug with an indication for treatment of smallpox". U.S. Food and Drug Administration (FDA).
  10. ^ Yang G, Pevear DC, Davies MH, Collett MS, Bailey T, Rippen S, et al. (October 2005). "An orally bioavailable antipoxvirus compound (ST-246) inhibits extracellular virus formation and protects mice from lethal orthopoxvirus Challenge". Journal of Virology. 79 (20): 13139–49. doi:10.1128/JVI.79.20.13139-13149.2005. PMC 1235851. PMID 16189015.
  • "Tecovirimat". Drug Information Portal. U.S. National Library of Medicine.
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