Riamilovir

Last updated

Riamilovir
Triazavirin.svg
Clinical data
Trade names Triazavirin
Other namesTZV
ATC code
Legal status
Legal status
  • RU: Rx-only
Identifiers
  • 2-methylsulfanyl-6-nitro[1,2,4]triazolo[5,1-c] [1,2,4]triazin-7(4H)-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.217.074 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C5H4N6O3S
Molar mass 228.19 g·mol−1
3D model (JSmol)
  • CSc1[nH]n2c(=O)c(nnc2n1)[N+](=O)[O-]
  • InChI=1S/C5H4N6O3S/c1-15-5-6-4-8-7-2(11(13)14)3(12)10(4)9-5/h1H3,(H,6,8,9)
  • Key:IDVQGNMSSHPZSJ-UHFFFAOYSA-N

Riamilovir, sold under the brand name Triazavirin, is a broad-spectrum antiviral drug developed in Russia through a joint effort of Ural Federal University, Russian Academy of Sciences, Ural Center for Biopharma Technologies and Medsintez Pharmaceutical. [1] It has a novel triazolotriazine core, which represents a new structural class of non-nucleoside antiviral drugs. [2]

Contents

The principal action of riamilovir is to inhibit the synthesis of viral ribonucleic acid (RNA) and the replication of viral genomic fragments through its synthetic analogue to the bases of purine nucleosides. [3] [4] [5]

Medical uses

Riamilovir is used to treat influenza.

Research

It was originally developed as a potential treatment for pandemic influenza strains such as H5N1, and most of the testing that has been done has focused on its anti-influenza activity. [5] [3] [6] [7] [8] However, riamilovir has also been found to have antiviral activity against a number of other viruses including tick-borne encephalitis virus, [4] [9] and is also being investigated for potential application against a lethal influenza infection and secondary bacterial pneumonia following influenza, [10] Lassa fever and Ebola virus disease. [11] [12] [13] [14] [15] Riamilovir has passed clinical trials and has shown antiviral activity against ARVI. [16] [17] [18] [19] In 2020, testing of riamilovir was started against SARS-CoV-2 in Russia, China, [20] and South Africa. [21] [22] [23] [24] [25] [26] [ excessive citations ] Randomized, double-blind, multicenter trial published in 2024 show that Riamilovir has demonstrated efficacy in both treating and preventing COVID-19. [27] [28]

In August 2014, the Ministry of Health of Russia issued a registration certificate for riamilovir (Triazavirin). [29] The active substance of the drug triazavirin is a new active molecule, [2] and can be dispensed by prescription. The production of riamilovir is carried out at a modern pharmaceutical enterprise LLC "Plant Medsintez". [1] The registration procedure for riamilovir has begun in the Republic of South Africa. [25]

See also

References

  1. 1 2 "Triazaverin Is Officially Recommended". www.medsintez.com. Retrieved 25 February 2021.
  2. 1 2 Rusinov VL, Sapozhnikova IM, Ulomskii EN, Medvedeva NR, Egorov VV, Kiselev OI, et al. (2015). "Nucleophilic substitution of nitro group in nitrotriazolotriazines as a model of potential interaction with cysteine-containing proteins". Chemistry of Heterocyclic Compounds. 51 (3): 275–280. doi: 10.1007/s10593-015-1695-4 . S2CID   83702396.
  3. 1 2 Karpenko I, Deev S, Kiselev O, Charushin V, Rusinov V, Ulomsky E, et al. (May 2010). "Antiviral properties, metabolism, and pharmacokinetics of a novel azolo-1,2,4-triazine-derived inhibitor of influenza A and B virus replication". Antimicrobial Agents and Chemotherapy. 54 (5): 2017–2022. doi:10.1128/AAC.01186-09. PMC   2863629 . PMID   20194696.
  4. 1 2 Loginova SI, Borisevich SV, Rusinov VL, Ulomskiĭ UN, Charushin VN, Chupakhin ON (2014). "[Investigation of Triazavirin antiviral activity against tick-borne encephalitis pathogen in cell culture]". Antibiotiki i Khimioterapiia (in Russian). 59 (1–2): 3–5. PMID   25051708.
  5. 1 2 Loginova SI, Borisevich SV, Maksimov VA, Bondarev VP, Kotovskaia SK, Rusinov VL, et al. (2007). "[Investigation of triazavirin antiviral activity against influenza A virus (H5N1) in cell culture]". Antibiotiki i Khimioterapiia (in Russian). 52 (11–12): 18–20. PMID   19275052.
  6. ↑ Kiselev OI, Deeva EG, Mel'nikova TI, Kozeletskaia KN, Kiselev AS, Rusinov VL, et al. (2012). "[A new antiviral drug Triazavirin: results of phase II clinical trial]". Voprosy Virusologii (in Russian). 57 (6): 9–12. PMID   23477247.
  7. ↑ Kasianenko KV, Lvov NI, Maltsev OV, Zhdanov KV (9 October 2019). "Nucleoside analogues for the treatment of influenza: History and experience". Journal of Infectology (in Russian). 11 (3): 20–26. doi: 10.22625/2072-6732-2019-11-3-20-26 . S2CID   241604614.
  8. ↑ Sologub TV, Tokin II, Midikari AS, Tsvetkov VV (2017). "A comparative efficacy and safety of using antiviral drugs in therapy of patients with influenza". Infekcionnye Bolezni (in Russian). 15 (3): 25–32. doi:10.20953/1729-9225-2017-3-25-32.
  9. ↑ Loginova SY, Borisevich SV, Rusinov VL, Ulomsky EN, Charushin VN, Chupakhin ON, et al. (2015). "[Investigation of Therapeutic Efficacy of Triazavirin Against Experimental Forest-Spring Encephalitis on Albino Mice]". Antibiotiki i Khimioterapiia (in Russian). 60 (7–8): 11–13. PMID   26863736.
  10. ↑ Leneva IA, Falynskova IN, Makhmudova NR, Glubokova EA, Kartashova NP, Leonova EI, et al. (22 February 2018). "Effect of triazavirine on the outcome of a lethal influenza infection and secondary bacterial pneumonia following influenza in mice". Microbiology Independent Research Journal. 4 (1). doi: 10.18527/2500-2236-2017-4-1-52-57 .
  11. ↑ "Target: Ebola". Pravda. 22 December 2014. Retrieved 18 January 2015.
  12. ↑ "Yekaterinburg pharmacies to sell domestic antiviral drug". Yekaterinburg News Reports. 6 January 2015. Archived from the original on 18 January 2015. Retrieved 18 January 2015.
  13. ↑ Cox S (17 October 2014). "Ebola crisis: Vaccine 'too late' for outbreak. BBC News, 17 October 2014". BBC News.
  14. ↑ Bora K (12 November 2014). "Russia Will Begin Testing Triazavirin, Used For Lassa Fever, And Other Drugs On Ebola: Health Ministry". International Business Times.
  15. ↑ Kezina D (12 November 2014). "New antiviral drug from Urals will help fight Ebola and other viruses". Russia Beyond the Headlines.
  16. ↑ Tikhonova EP, Kuz'mina TY, Andronova NV, Tyushevskaya OA, Elistratova TA, Kuz'min AE (15 April 2018). "Study of effectiveness of antiviral drugs (umifenovir, triazavirin) against acute respiratory viral infections". Kazan Medical Journal (in Russian). 99 (2): 215–223. doi: 10.17816/KMJ2018-215 . ISSN   2587-9359.
  17. ↑ Verevshchikov VK, Shemyakina EK, Sabitov AU, Khamanova YB (2019). "The Possibilities of Etiotropic Therapy for Influenza and ARVI with Taking into Account the Period of Hospitalization and the Risk of Developing Secondary Complications". Antibiotics and Chemotherapy. Retrieved 25 February 2021.
  18. ↑ Lioznov DA, Tokin II, Zubkova TG, Sorokin PV (December 2020). "[The practice of using a domestic antiviral drug in the etiotropic therapy of acute respiratory viral infection]". Terapevticheskii Arkhiv (in Russian). 92 (12): 160–164. doi: 10.26442/00403660.2020.12.200427 . PMID   33720589.
  19. ↑ Verevshchikov VK, Shemyakina EK, Sabitov AU, Batskalevich NA (2018). "Modern Etiotropic Therapy of Influenza and ARVI in Adult Patients with Premorbid Pathology". Antibiotics and Chemotherapy. Retrieved 25 February 2021.
  20. ↑ Zheng B, Zhao Q, Yang W, Feng P, Xin C, Ying Y, et al. (March 2024). "Small-molecule antiviral treatments for COVID-19: A systematic review and network meta-analysis". International Journal of Antimicrobial Agents. 63 (3): 107096. doi: 10.1016/j.ijantimicag.2024.107096 . PMID   38244811.{{cite journal}}: CS1 maint: article number as page number (link)
  21. ↑ Jamshaid U (4 February 2020). "China Testing Russia's Triazavirin As Coronavirus Treatment". Russian Health Ministry. Urdupoint.
  22. ↑ Phiri C (5 February 2020). "China Tests Russian Antiviral Drug Which Might Treat Coronavirus As Moscow Warns Of Possible 'Mass Outbreak'". Zambia Reports. Archived from the original on 5 February 2020. Retrieved 11 February 2020.
  23. ↑ Wu X, Yu K, Wang Y, Xu W, Ma H, Hou Y, et al. (October 2020). "Efficacy and Safety of Triazavirin Therapy for Coronavirus Disease 2019: A Pilot Randomized Controlled Trial". Engineering. 6 (10): 1185–1191. Bibcode:2020Engin...6.1185W. doi: 10.1016/j.eng.2020.08.011 . PMC   7476906 . PMID   32923016. S2CID   221520816.
  24. ↑ Brandt K. "SA study to trial antiviral Triazavirin as COVID-19 treatment". ewn.co.za. Retrieved 25 February 2021.
  25. 1 2 "Discussion on Russia's antiviral drug Triazavirin". SABC News. 21 January 2021 – via YouTube.
  26. ↑ Sabitov AU, Belousov VV, Edin AS, Oleinichenko EV, Gladunova EP, Tikhonova EP, et al. (21 November 2020). "Practical Experience of Using Riamilovir in Treatment of Patients with Moderate COVID-19". Antibiotiki i Khimioterapiya. 65 (7–8): 27–30. doi: 10.37489/0235-2990-2020-65-7-8-27-30 . S2CID   229508119.
  27. ↑ Sabitov AU, Lioznov DA, Zhdanov KV, Tikhonova EP, Esaulenko EV, Kovtun OP, et al. (June 2024). "[Results of a randomized double-blind multicenter clinical trial of the efficacy and safety of riamilovir in the treatment of COVID-19]". Terapevticheskii Arkhiv. 96 (5): 517–522. doi: 10.26442/00403660.2024.05.202770 . PMID   38829814.
  28. ↑ Sabitov AU, Lioznov DA, Zhdanov KV, Tihonova EP, Esaulenko EV, Sorokin PV (April 2024). "[Results of a randomized double-blind multicenter clinical trial of the efficacy and safety of the drug riamilovir for the prevention of COVID-19]". Terapevticheskii Arkhiv. 96 (3): 280–285. doi: 10.26442/00403660.2024.03.202652 . PMID   38713044.
  29. ↑ "Triazavirin (Riamilovir)". State Register of Medicines of the Russian Federation (in Russian).
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