Umifenovir

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Umifenovir

Clinical data
Trade names	Arbidol
Other names	AR-1I9514
Pregnancy category	C
Routes of administration	By mouth (hard capsules, tablets)
ATC code	J05AX13 (WHO)
Legal status
Legal status	RU OTC[1] CN Rx-only[1] BY OTC[2]
Pharmacokinetic data
Bioavailability	40%
Metabolism	Hepatic, CYP3A4[4]
Elimination half-life	17–21 hours
Excretion	40% excrete as unchanged umifenovir in feces (38.9%) and urine (0.12%)[3]
Identifiers
IUPAC name ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylsulfanyl)methyl]-1H-indole-3-carboxylate
CAS Number	131707-25-0 N
PubChem CID	131411
DrugBank	DB13609 Y
ChemSpider	116151 Y
UNII	93M09WW4RU
KEGG	D10558
ChEBI	CHEBI:134730
ChEMBL	ChEMBL1214598
PDB ligand	75U (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID60895015
ECHA InfoCard	100.247.800
Chemical and physical data
Formula	C22H25BrN2O3S
Molar mass	477.42 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCOC(=O)c1c(n(c2c1c(c(c(c2)Br)O)CN(C)C)C)CSc3ccccc3
InChI 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)

Umifenovir, sold under the brand name Arbidol, is an antiviral medication for the treatment of influenza and COVID infections used in Russia^[5] 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.^[6]

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 ^[7][8] make it a promising candidate for further research as a potential therapeutic agent for the selective treatment of flavivirus infections.^[9] 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.^[10][11] The drug has been shown in studies to inhibit viral entry into target cells ^[12] and stimulate the immune response.