Favipiravir

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Favipiravir
200px
Names
IUPAC name
5-Fluoro-2-oxo-1H-pyrazine-3-carboxamide
Other names
T-705
Identifiers
259793-96-9
ChEMBL ChEMBL221722
ChemSpider 431002
Jmol 3D model Interactive image
PubChem 492405
  • InChI=1S/C5H4FN3O2/c6-2-1-8-5(11)3(9-2)4(7)10/h1H,(H2,7,10)(H,8,11)
    Key: ZCGNOVWYSGBHAU-UHFFFAOYSA-N
  • InChI=1/C5H4FN3O2/c6-2-1-8-5(11)3(9-2)4(7)10/h1H,(H2,7,10)(H,8,11)
    Key: ZCGNOVWYSGBHAU-UHFFFAOYAM
  • c1c(nc(c(=O)[nH]1)C(=O)N)F
Properties
C5H4FN3O2
Molar mass 157.10 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Favipiravir, also known as T-705 or Avigan, is an experimental antiviral drug being developed by Toyama Chemical of Japan with activity against many RNA viruses. Like some other experimental antiviral drugs (T-1105 and T-1106), it is a pyrazinecarboxamide derivative. Favipiravir is active against influenza viruses, West Nile virus, yellow fever virus, foot-and-mouth disease virus as well as other flaviviruses, arenaviruses, bunyaviruses and alphaviruses.[1] Activity against enteroviruses [2] and Rift Valley fever virus has also been demonstrated.[3]

The mechanism of its actions is thought to be related to the selective inhibition of viral RNA-dependent RNA polymerase.[4] Other research suggests that favipiravir induces lethal RNA transversion mutations, producing a nonviable viral phenotype.[5] Favipiravir is a prodrug and is metabolized to its active form, favirpiravir-RTP, following digestion.[6] Human hypoxanthine guanine phosphoribosyltransferase (HGPRT) is believed to play a key role in this activation process.[7] Favipiravir does not inhibit RNA or DNA synthesis in mammalian cells and is not toxic to them.[1]

In 2014, favipiravir was approved in Japan for stockpiling against influenza pandemics.[8]

Ebola virus disease

The drug appears to be effective in a mouse model of Ebola virus disease, but its efficacy against human Ebola infection is unproved.[9][10][11] During the 2014 West Africa Ebola virus outbreak, it was reported that a French nurse who contracted Ebola while volunteering for MSF in Liberia recovered after receiving a course of favipiravir.[12] A clinical trial investigating the use of favipiravir against Ebola virus disease was started in Guéckédou, Guinea, during December 2014.[13] Preliminary results showed a decrease in mortality rate in patients with low-to-moderate levels of Ebola virus in the blood, but no effect on patients with high levels of the virus, a group at a higher risk of death.[14] The trial design has been criticised by Scott Hammer and others for using only historical controls.[15] The results of this clinical trial have been presented in February at the annual Conference on Retroviruses and Opportunistic Infections (CROI) 2016 by Daouda Sissoko[16] and published on March 1, 2016 in PLOS Medicine.[17]

See also

References

  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Caroline AL, Powell DS, Bethel LM, Oury TD, Reed DS, et al. (2014) Broad Spectrum Antiviral Activity of Favipiravir (T-705): Protection from Highly Lethal Inhalational Rift Valley Fever. PLoS Neglected Tropical Diseases 8(4): e2790. doi:10.1371/journal.pntd.0002790
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ http://www.msn.com/en-gb/news/world/french-nurse-cured-of-ebola-contracted-in-liberia/ar-BB7r1UJ
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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