Umifenovir

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Umifenovir
Arbidol.svg
Umifenovir ball-and-stick model.png
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
Legal status
Routes of
administration		 Oral (hard capsules, tablets)
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
ChEMBL CHEMBL1214598
Chemical data
Formula C22H28BrClN2O4S
Molecular mass 531.89 g/mol
  • CCOC(=O)c1c(n(c2c1c(c(c(c2)Br)O)CN(C)C)C)CSc3ccccc3
  • InChI=1S/C22H25BrN2O3S/c1-5-28-22(27)20-18(13-29-14-9-7-6-8-10-14)25(4)17-11-16(23)21(26)15(19(17)20)12-24(2)3/h6-11,26H,5,12-13H2,1-4H3 N
  • Key:KCFYEAOKVJSACF-UHFFFAOYSA-N N
 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

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External links

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Recommended INN: List 65., WHO Drug Information, Vol. 25, No. 1, 2011, page 91
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Продажи арбидола упали на треть (in Russian)
  5. ↑ 5.0 5.1 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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ http://www.vidal.ru/poisk_preparatov/arbidol.htm
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