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Triazavirin
Identification
- Name
- Triazavirin
- Accession Number
- DB15622
- Description
Triazavirin is a guanine nucleotide analog antiviral originally developed in Russia that has shown efficacy against influenza A and B, including the H5N1 strain.1,2,4 It appears that Triazavirin has shown promise in reducing influenza disease severity and associated complications.5 Given the similarities between SARS-CoV-2 and H5N1, health officials are investigating Triazavirin as an option to combat SARS-CoV-2, the coronavirus responsible for COVID-19.2
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Triazavirin (DB15622)
- Weight
- Average: 228.19
Monoisotopic: 228.006559187 - Chemical Formula
- C5H4N6O3S
- Synonyms
- Riamilovir
- Triazavirin
Pharmacology
- Indication
Triazavirin was developed in Russia as a potential treatment of Influenza A and B infections.3
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Triazavirin is a guanosine nucleotide analog that inhibits RNA synthesis.4,6
- Absorption
In rabbits, intragastric triazavirin reaches a Cmax of 1.1±0.1mg/L, with a Tmax of 0.40±0.16h, and an AUC of 3.10±0.8mg*h/L.3 In rabbits, intravenous triazavirin has an AUC of 1.2±0.3mg*h/L.3
In humans, triazavirin reaches a Cmax of 4.8µg/mL, with a Tmax of 1-1.5h, and an AUC of 12.8µgµg/h*mL.6
- Volume of distribution
In rabbits, intragastric triazavirin has a volume of distribution of 83.5±19.2L/kg while intravenous triazavirin has a volume of distribution of 1.2±0.3L/kg.3
- Protein binding
Data regarding the protein binding of triazavirin is not readily available.
- Metabolism
Data regarding the metabolism of triazavirin is not readily available.
- Route of elimination
Data regarding the route of elimination of triazavirin is not readily available.
- Half-life
In rabbits, intragastric triazavirin has a half life of 1.1±0.1h while intravenous triazavirin has a half life of 0.50±0.09h.3
The half life of triazavirin is 1-1.5h.6
- Clearance
In rabbits, intragastric triazavirin has a clearance of 37.0±11.2L/h*kg while intravenous triazavirin has a clearance of 14.0±3.7L/h*kg.3
The clearance of triazavirin is 246mL/min.6
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
The intraperitoneal LD50 of triazavirin in mice is 1400±120mg/kg in mice and the intragastric LD50 is 2200±96mg/kg.3
Patients experiencing an overdose may present with nausea, vomiting, dyspepsia, and stomach pain.6 Treat overdose with symptomatic and supportive treatment, which may include discontinuation of treatment.6
- Affected organisms
- Influenza A virus
- Influenza B virus
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Take with or without food.
Products
Categories
- Drug Categories
- Classification
- Not classified
Chemical Identifiers
- UNII
- F2HTG1MH2D
- CAS number
- 123606-06-4
- InChI Key
- IDVQGNMSSHPZSJ-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 7-(methylsulfanyl)-3-nitro-1H,4H-[1,2,4]triazolo[3,2-c][1,2,4]triazin-4-one
- SMILES
- CSC1=NN2C(NN=C(C2=O)[N+]([O-])=O)=N1
References
- General References
- Kiselev OI, Deeva EG, Mel'nikova TI, Kozeletskaia KN, Kiselev AS, Rusinov VL, Charushin VN, Chupakhin ON: [A new antiviral drug Triazavirin: results of phase II clinical trial]. Vopr Virusol. 2012 Nov-Dec;57(6):9-12. [PubMed:23477247]
- Vincent MJ, Bergeron E, Benjannet S, Erickson BR, Rollin PE, Ksiazek TG, Seidah NG, Nichol ST: Chloroquine is a potent inhibitor of SARS coronavirus infection and spread. Virol J. 2005 Aug 22;2:69. doi: 10.1186/1743-422X-2-69. [PubMed:16115318]
- Karpenko I, Deev S, Kiselev O, Charushin V, Rusinov V, Ulomsky E, Deeva E, Yanvarev D, Ivanov A, Smirnova O, Kochetkov S, Chupakhin O, Kukhanova M: Antiviral properties, metabolism, and pharmacokinetics of a novel azolo-1,2,4-triazine-derived inhibitor of influenza A and B virus replication. Antimicrob Agents Chemother. 2010 May;54(5):2017-22. doi: 10.1128/AAC.01186-09. Epub 2010 Mar 1. [PubMed:20194696]
- Shvetsov A, Zabrodskaya Y, Nekrasov P, Egorov V: Triazavirine supramolecular complexes as modifiers of the peptide oligomeric structure Journal of Biomolecular Structure and Dynamics. 2017 Sep 12;36(10):2694-2698.
- RT Question More: China tests Russian anti-viral drug which might treat coronavirus as Moscow warns of possible 'mass outbreak' [Link]
- Triazavirin [Link]
- External Links
- ChemSpider
- 2367718
- ChEMBL
- CHEMBL1618116
- ZINC
- ZINC000100546686
- Wikipedia
- Triazavirin
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 2.038 ChemSpider - Predicted Properties
Property Value Source Water Solubility 1.67 mg/mL ALOGPS logP 1.07 ALOGPS logP 1.67 ChemAxon logS -2.1 ALOGPS pKa (Strongest Acidic) 6.64 ChemAxon pKa (Strongest Basic) -4.7 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 115.31 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 51.45 m3·mol-1 ChemAxon Polarizability 19.18 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Drug created on March 04, 2020 10:00 / Updated on June 30, 2020 20:41
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