Umifenovir

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Umifenovir

Clinical data
Trade names	Arbidol
Other names	AR-1I9514
Pregnancy category	C
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
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.

Status

Testing of umifenovir's efficacy has mainly occurred in China and Russia,^[13][14] and it is well known in these two countries.^[15] Some of the Russian tests showed the drug to be effective^[13] and a direct comparison with oseltamivir showed similar efficiency in vitro and in a clinical setting.^[16] In 2010 Arbidol was the drug brand with the highest sales volume in Russia.^[17] In the first quarter of 2020 it had a 16 percent share in the Russian antiviral market.^[18]

Mode of action

Biochemistry

Umifenovir inhibits membrane fusion of influenza virus.

Some evidence suggests that the drug's actions are more effective at preventing infections from RNA viruses than infections from DNA viruses.^[20]

As well as specific antiviral action against both

Umifenovir is used primarily as an antiviral treatment for influenza. The drug has also been investigated as a candidate drug for treatment of hepatitis C.^[22]

More recent studies indicate that umifenovir also has in vitro effectiveness at preventing entry of Zaire ebolavirus (Kikwit strain), Tacaribe arenavirus and Kaposi's sarcoma-associated herpesvirus in 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.^[23][24]

Side effects

In 2007, the Russian Academy of Medical Sciences stated that the effects of Arbidol (umifenovir) are not scientifically proven.[26]

Russian media criticized lobbying attempts by Tatyana Golikova (then-Minister of Healthcare) to promote umifenovir,^[27] and the unsubstantiated claim that Arbidol can speed up recovery from flu or cold by 1.3-2.3 days.^[28] They also made claims that comparative clinical studies have proven umifenovir to be inefficient.^[29][30]

Names

Arbidol is the INN.^[31]

The brand name Arbidol is known as Russian: Арбидол and Chinese: 阿比朵尔.^{[citation needed]}

Research

In early 2020 umifenovir was touted as a potential treatment for COVID-19 in China, where it was sometimes given to patients in combination with other drugs such as the anti-HIV drug Darunavir.^{[32][33][34][35]} A three-arm RCT study published in May 2020 in the Cell Press journal Clinical Advances found that neither Umifenovir or Lopinavir/Ritonavir helped patients with mild to moderate COVID-19.^[36] A similar study comparing Umifenovir directly with Lopinavir/Ritonavir found no difference in fever duration between the two groups but found a lower viral load on day 14 in the Umifenovir group.^[37] A systemic review and meta-analysis of 16 studies on Umifenovir published in March 2021 concluded that there is "no significant benefit of using Arbidol compared with non‐antiviral treatment or other therapeutic agents against COVID‐19 disease."^[38]

References