Umifenovir

Umifenovir
Systematic (IUPAC) name
1-methyl-2-((phenylthio)methyl)-3-carbethoxy-4-((dimethylamino)methyl)-5-hydroxy-6-bromindole
Clinical data
Trade names Arbidol
Pregnancy
category
  • N/A
Routes of
administration		 Oral (hard capsules, tablets)
Legal status
Pharmacokinetic data
Bioavailability 40%
Metabolism Hepatic
Biological half-life 17–21 hours
Excretion 40% excrete as unchanged umifenovir in feces (38,9%) and urine (0,12%)[1]
Identifiers
CAS Number 131707-23-8 N
ATC code L03AX (WHO)
PubChem CID 9958103
DrugBank N/A N
ChemSpider 116151 N
UNII 93M09WW4RU YesY
Chemical data
Formula C22H28BrClN2O4S
Molar mass 531.89 g/mol
 NYesY (what is this?)  (verify)

Umifenovir[2] (trade name Russian: Арбидол, Chinese: 阿比朵尔) is an antiviral treatment for influenza infection used in Russia[3] and China. The drug is manufactured by Pharmstandard (Russian: Фармстандарт) and since 2005 it has been the number one best-selling over-the-counter drug in Russia.[4] Although some Russian studies have shown it to be effective, it is not approved for use in Western countries. Chemically, umifenovir features an indole core, functionalized at all but one positions with different substituents. The drug inhibits viral entry into target cells and also stimulates the immune response.

Umifenovir is manufactured and made available as both tablets and capsules.

Status

Testing of umifenovir's efficacy has mainly occurred in China and Russia,[5][6] and it is well known in these two countries.[7]

Some of the Russian tests showed the drug to be effective.[5]

Mode of action

Biochemistry

Umifenovir inhibits membrane fusion.[3] Umifenovir prevents contact between the virus and target host cells. Fusion between the viral capsid and the cell membrane of the target cell is inhibited. This prevents viral entry to the target cell, and therefore protects it from infection.[8]

Some evidence suggests that the drug's actions are more effective at preventing infections from RNA viruses than infections from DNA viruses.[9]

As well as specific antiviral action against both influenza A and influenza B viruses, umifenovir exhibits modulatory effects on the immune system. The drug stimulates a humoral immune response, induces interferon-production, and stimulates the phagocytic function of macrophages.[10]

Clinical application

Umifenovir is used primarily as an antiviral treatments for influenza. The drug has also been investigated as a candidate drug for treatment of hepatitis C.[11]

A more recent study (published online as an accepted manuscript by the Journal of Virology) by Pécheur et al indicates that umifenovir also has in vitro effectiveness at preventing entry of Ebolavirus Zaïre Kikwit, Tacaribe arenavirus and human herpes virus 8 into mammalian cell cultures, while confirming umifenovir's suppressive effect in vitro on Hepatitis B and poliovirus infection of mammalian cells when introduced either in advance of viral infection or during infection.[12]

Side effects

Side effects in children include sensitization to the drug. No known overdose cases have been reported and allergic reactions are limited to people with hypersensitivity. The LD50 is more than 4 g/kg.[13]

References

  1. ↑ "Full Prescribing Information: Arbidol® (umifenovir) film-coated tablets 50 and 100 mg: Corrections and Additions". State Register of Medicines (in Russian). Open joint-stock company “Pharmstandard-Tomskchempharm”. Retrieved 3 June 2015.
  2. ↑ Recommended INN: List 65., WHO Drug Information, Vol. 25, No. 1, 2011, page 91
  3. 1 2 Leneva IA, Russell RJ, Boriskin YS, Hay AJ (February 2009). "Characteristics of arbidol-resistant mutants of influenza virus: implications for the mechanism of anti-influenza action of arbidol". Antiviral Res. 81 (2): 132–40. doi:10.1016/j.antiviral.2008.10.009. PMID 19028526.
  4. ↑ Продажи арбидола упали на треть (in Russian)
  5. 1 2 Leneva IA, Fediakina IT, Gus'kova TA, Glushkov RG (2005). "[Sensitivity of various influenza virus strains to arbidol. Influence of arbidol combination with different antiviral drugs on reproduction of influenza virus A]". Терапевтический Архив (Therapeutic Archive) (Russian translation) (Moscow, Russia: ИЗДАТЕЛЬСТВО "МЕДИЦИНА") 77 (8): 84–88. PMID 16206613. Retrieved 2008-02-22.
  6. ↑ Wang MZ, Cai BQ, Li LY; et al. (2004). "[Efficacy and safety of arbidol in treatment of naturally acquired influenza]". Zhongguo Yi Xue Ke Xue Yuan Xaue Bao (in Chinese) 26 (3): 289–93. PMID 15266832.
  7. ↑ Boriskin YS, Leneva IA, Pécheur EI, Polyak SJ (2008). "Arbidol: a broad-spectrum antiviral compound that blocks viral fusion". Curr. Med. Chem. 15 (10): 997–1005. doi:10.2174/092986708784049658. PMID 18393857.
  8. ↑ Boriskin YS, Pécheur EI, Polyak SJ (2006). "Arbidol: a broad-spectrum antiviral that inhibits acute and chronic HCV infection". Virol. J. 3: 56. doi:10.1186/1743-422X-3-56. PMC 1559594. PMID 16854226.
  9. ↑ Shi L, Xiong H, He J; et al. (2007). "Antiviral activity of arbidol against influenza A virus, respiratory syncytial virus, rhinovirus, coxsackie virus and adenovirus in vitro and in vivo". Arch. Virol. 152 (8): 1447–55. doi:10.1007/s00705-007-0974-5. PMID 17497238.
  10. ↑ Glushkov RG, Gus'kova TA, Krylova LIu, Nikolaeva IS (1999). "[Mechanisms of arbidole's immunomodulating action]". Vestn. Akad. Med. Nauk SSSR (in Russian) (3): 36–40. PMID 10222830.
  11. ↑ Pécheur EI, Lavillette D, Alcaras F et al. (2007). "Biochemical mechanism of hepatitis C virus inhibition by the broad-spectrum antiviral arbidol". Biochemistry 46 (20): 6050–9. doi:10.1021/bi700181j. PMC 2532706. PMID 17455911.
  12. ↑ Pécheur EI, Borisevich V, Hlafmann P et al. (January 2016). "The Synthetic Antiviral Drug Arbidol Inhibits Globally Prevalent Pathogenic Viruses" (PDF). Journal of Virology 90 ((accepted manuscript posted online)). doi:10.1128/JVI.02077-15.
  13. ↑ http://www.vidal.ru/poisk_preparatov/arbidol.htm

External links

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