Umifenovir

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Structural formula
Umifenovir structural formula
General
Non-proprietary name Umifenovir
other names
  • 6-Bromo-4- (dimethylaminomethyl) -5-hydroxy-1-methyl-2- (phenylsulfanylmethyl) indole-3-carboxylic acid ethyl ester
  • Ethyl {6-bromo-4 - [(dimethylamino) methyl] -5-hydroxy-1-methyl-2 - [(phenylsulfanyl) methyl] -1H-indole-3-carboxylate}
Molecular formula C 22 H 25 BrN 2 O 3 S
External identifiers / databases
CAS number 131707-25-0
EC number 814-571-6
ECHA InfoCard 100,247,800
PubChem 131411
ChemSpider 116151
DrugBank DB13609
Wikidata Q27271599
Drug information
ATC code

J05 AX13

Drug class

Antiviral

Mechanism of action

Fusion inhibitor

properties
Molar mass 477.41 g mol −1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Umifenovir is an active ingredient from the group of antivirals . In Russia, the drug is approved under the brand name Arbidol for the oral treatment of various viral infections , including influenza A and B, and approvals are also expected in China.

Pharmaceutically used salts are umifenovir hydrochloride or umifenovir hydrochloride monohydrate.

Mechanism of action

Umifenovir is a fusion inhibitor , which means it interacts with the virus ' hemagglutinin and prevents the virus' lipid membrane ( virus envelope ) from fusing with the host cell's cell membrane. This prevents viruses from entering the host cell.

The instructions for use of Arbidol describe in-vitro inhibition of influenza A and B viruses in particular , including the highly pathogenic subtypes A-H1N1-pdm09 and A-H5N1 , as well as other pathogens causing acute respiratory viral infections ( Acute Respiratory Viral Infections, ARVI ) associated with severe acute respiratory syndrome (SARS) (such as coronaviruses ); furthermore rhinoviruses , adenoviruses , pneumoviruses and parainfluenza virus ( paramyxoviruses ) are given.

Umifenovir is said not only to have a specific antiviral effect against influenza A and influenza B viruses, but also to have modulatory effects on the immune system.

Therapeutic and experimental use

In Russia Umifenovir than Arbidol approved for prevention against and treatment of influenza A and B, other acute viral respiratory infections, acute to treat intestinal infections Rotavirus - aetiology , and for non-specific prophylaxis and treatment of severe acute respiratory syndrome (SARS).

In 2020 umifenovir will be tested for the therapy of Covid-19 . In a study carried out in Wuhan on moderately ill patients, almost 56 percent had recovered after seven days. In a comparison group given favipiravir , the rate was 71 percent. In a smaller group of seriously ill patients at the start of therapy, there was no clear difference. However, the results of this study are questioned.

Individual evidence

  1. ↑ Registration dossier on ethyl 6-bromo-4 - [(dimethylamino) methyl] -5-hydroxy-1-methyl-2 (phenylsulfanylmethyl) indole-3-carboxylate ( GHS section ) at the European Chemicals Agency (ECHA), accessed on 12. July 2020.
  2. ↑ Vidal , accessed March 30, 2020 (Russian).
  3. ↑ 重大 突破！ 阿比朵尔 和 达 芦 那 韦 可抑制 新 冠 病毒 , cj.sina.com, February 5, 2020 (Chinese).
  4. ↑ Китай официально признал "Арбидол" лекарством против коронавируса , " The Bell ", February 19, 2020 (Russian).
  5. ↑ External identifiers or database links for umifenovir hydrochloride : CAS number: 131707-23-8, EC number: 680-680-9, ECHA InfoCard: 100.205.811 , PubChem : 9958103 , ChemSpider : 8133712 , Wikidata : Q4475505 . UNII: 8CXV4OU367
  6. ↑ External identifiers or database links to umifenovir hydrochloride monohydrate : CAS number: 868364-57-2, PubChem : 131410 , ChemSpider : 116150 , Wikidata : Q27294496 . UNII: YFE0A1FOSX
  7. ↑ YS Boriskin et al .: Arbidol: a broad-spectrum antiviral that inhibits acute and chronic HCV infection . Virology Journal, Volume 56 (2006) doi: 10.1186 / 1743-422X-3-56 PMC 1559594 (free full text)
  8. ↑ a b Vidal: Instructions for use Arbidol suspension for oral administration , accessed on March 30, 2020.
  9. ^ RG Glushkov et al .: Mekhanizmy immunomoduliruiushchego deĭstviia arbidola [Mechanisms of arbidole's immunomodulating action] . Vestnik Rossiiskoi Akademii Meditsinskikh Nauk, Volume 3 (1999), pp. 36-40. PMID 10222830 .
  10. ↑ Kazuhiro Nogi: What can the flu drug Avigan, which the federal government is buying, do? In: spiegel.de. April 2, 2020, accessed April 2, 2020 .
  11. ↑ Anja Martini, Christian Drosten : Coronavirus Update. (PDF) Episode 22. In: ndr.de. Norddeutscher Rundfunk, March 26, 2020, p. 6 f. , accessed on March 27, 2020 .