Tecovirimat

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Tecovirimat
Tecovirimat.svg
Names
Trade namesTpoxx
Other namesST-246
  • N-{3,5-Dioxo-4-azatetracyclo[5.3.2.0{2,6}.0{8,10}]dodec-11-en-4- yl}-4-(trifluoromethyl)benzamide
Clinical data
Main usesSmallpox, monkeypox, cowpox, complications of smallpox vaccination[1]
Side effectsNausea, headache, abdominal pain[2]
Pregnancy
category
  • US: N (Not classified yet)
Routes of
use
By mouth
Typical dose600 mg BID[2]
External links
AHFS/Drugs.comMonograph
US NLMTecovirimat
Legal
Legal status
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, is an antiviral medication with activity against smallpox.[2] Other uses may include monkeypox, cowpox, and complications of smallpox vaccination.[1] It is taken by mouth.[2]

Common side effects include nausea, headache, and abdominal pain.[2] No serious side effects have been seen.[4] It works by blocking orthopoxvirus VP37 protein, which prevents the virus from leave a cell.[2]

Tecovirimat was approved for medical use in the United States in 2018.[2] Two million doses are in the US Strategic National Stockpile in the event that smallpox reoccurs.[5] As of 2021 it is not approved in Europe.[1]

Medical uses

Tecovirimat was first used for treatment in December 2018 after a laboratory-acquired vaccinia virus infection.[6]

Evidence

The results of trials support 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 permitted for 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]

Dosage

In those over 40 kg it is taken at a dose of 600 mg twice per day for two weeks.[2]

Mechanism of action

Tecovirimat inhibits the function of a major envelope protein required for the production of extracellular virus. The drug prevents the virus from leaving an infected cell, hindering the spread of the virus within the body.[9]

History

It was the first antipoxviral drug approved in the United States.[10] The U.S. Food and Drug Administration (FDA) considers it to be a first-in-class medication.[11]

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.[12]

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. 1.0 1.1 1.2 "Tecovirimat". SPS - Specialist Pharmacy Service. 17 July 2018. Retrieved 24 September 2021.
  2. 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 "Tecovirimat Monograph for Professionals". Drugs.com. Retrieved 24 September 2021.
  3. "U.S. Food and Drug Administration Approves SIGA Technologies' TPOXX (tecovirimat) for the Treatment of Smallpox - SIGA". SIGA.
  4. McNeil Jr DG. "Drug to Treat Smallpox Approved by F.D.A., a Move Against Bioterrorism". The New York Times. Retrieved 16 July 2018.
  5. Cunningham A (13 July 2018). "FDA approves the first smallpox treatment".
  6. Whitehouse ER, Rao AK, Yu YC, et al. Novel Treatment of a Vaccinia Virus Infection from an Occupational Needlestick — San Diego, California, 2019. MMWR Morb Mortal Wkly Rep 2019;68:943–946. DOI:10.15585/mmwr.mm6842a2
  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. 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.
  10. "FDA approves the first drug with an indication for treatment of smallpox". U.S. Food and Drug Administration (FDA) (Press release). 13 July 2018. Retrieved 1 August 2018.
  11. New Drug Therapy Approvals 2018 (PDF). U.S. Food and Drug Administration (FDA) (Report). January 2019. Retrieved 16 September 2020.
  12. 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).

External links

Identifiers: