Umifenovir

Umifenovir, sold under the brand name Arbidol, is an antiviral medication for the treatment of influenza and COVID infections used in Russia and China. The drug is manufactured by Pharmstandard (Russian: Фармстандарт). It is not approved by the U.S. Food and Drug Administration (FDA) for the treatment or prevention of influenza.

Umifenovir
Clinical data
Trade namesArbidol
Other namesAR-1I9514
Pregnancy
category
  • C
Routes of
administration
By mouth (hard capsules, tablets)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability40%
MetabolismHepatic, CYP3A4
Elimination half-life17–21 hours
Excretion40% excrete as unchanged umifenovir in feces (38.9%) and urine (0.12%)
Identifiers
  • ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylsulfanyl)methyl]-1H-indole-3-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.247.800
Chemical and physical data
FormulaC22H25BrN2O3S
Molar mass477.42 g·mol−1
3D model (JSmol)
  • 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
 NY (what is this?)  (verify)

Chemically, umifenovir features an indole core, functionalized at all but one positions with different substituents. The molecular groups of umifenovir - hydroxy, amino and carboxy - can interact to form various hydrogen-bonded synthons. Antiviral activity and acceptable cytotoxicity profiles make it a promising candidate for further research as a potential therapeutic agent for the selective treatment of flavivirus infections . Umifenovir is characterized by only one polymorphic form but can exist in the form of a large number of crystal solvates, the production of which depends on the medium and conditions of synthesis. In this case, the implementation of the crystal solvate or other solid form may be determined by the spatial structure and conformational equilibria in the saturated solution . The drug has been shown in studies to inhibit viral entry into target cells and stimulate the immune response.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.