NAV

Triazavirin

Identification

Summary

Triazavirin is an antiviral used to treat several strains of influenza.

Generic Name
Triazavirin
DrugBank Accession Number
DB15622
Background

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
3D
Similar Structures
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

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Contraindications & Blackbox Warnings
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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
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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

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.

Categories

Drug Categories
Classification
Not classified
Affected organisms
  • Influenza A virus
  • Influenza B virus

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
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. RT Question More: China tests Russian anti-viral drug which might treat coronavirus as Moscow warns of possible 'mass outbreak' [Link]
  6. Triazavirin [Link]
ChemSpider
2367718
ChEMBL
CHEMBL1618116
ZINC
ZINC000100546686
Wikipedia
Triazavirin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19)1
2, 3TerminatedTreatmentCoronavirus Disease 2019 (COVID‑19)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP2.038ChemSpider
Predicted Properties
PropertyValueSource
Water Solubility1.67 mg/mLALOGPS
logP1.07ALOGPS
logP1.67ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)6.64ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area115.31 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.45 m3·mol-1ChemAxon
Polarizability19.18 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Drug created at March 04, 2020 17:00 / Updated at July 01, 2020 02:41