NAV

Taribavirin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Taribavirin
DrugBank Accession Number
DB06408
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 243.223
Monoisotopic: 243.096753919
Chemical Formula
C8H13N5O4
Synonyms
  • Ribavirin amidine
  • Taribavirin
  • Viramidine
External IDs
  • ICN 3142
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Pharmacology

Indication

Investigated for use/treatment in hepatitis (viral, C).

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

The prodrug taribavirin (1-b-D-ribofuranosyl-1H-1, 2, 4-triazole-3-carboxamidine) is a synthetic nucleoside (guanosine) analog under development for the treatment of patients with chronic hepatitis C. Taribavirin is metabolized by the liver and converted into its active metabolite, ribavirin. This pathway reduces exposure to red blood cells (RBCs) and increases exposure to the liver, the site of HCV replication. [Valeant Website] Ribavirin is readily phosphorylated intracellularly by adenosine kinase to ribavirin mono-, di-, and triphosphate metabolites. Ribavirin triphosphate (RTP) is a potent competitive inhibitor of inosine monophosphate (IMP) dehydrogenase, viral RNA polymerase and messenger RNA (mRNA) guanylyltransferase (viral). Guanylyltranserase inhibition stops the capping of mRNA. These diverse effects result in a marked reduction of intracellular guanosine triphosphate (GTP) pools and inhibition of viral RNA and protein synthesis. Ribavirin is also incorporated into the viral genome causing lethal mutagenesis and a subsequent decrease in specific viral infectivity.

TargetActionsOrganism
UDNANot AvailableHumans
URNA-directed RNA polymerase LNot AvailableHPIV-2
UEctonucleotide pyrophosphatase/phosphodiesterase family member 1Not AvailableHumans
URNA-directed RNA polymerase catalytic subunitNot AvailableInfluenza A virus (strain A/Beijing/11/1956 H1N1)
UCytosolic purine 5'-nucleotidaseNot AvailableHumans
UInosine-5'-monophosphate dehydrogenase 1Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

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.
DrugInteraction
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interactions in your software
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Taribavirin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Taribavirin.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Taribavirin.
Bacillus calmette-guerin substrain russian BCG-I live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Taribavirin.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Taribavirin.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Taribavirin hydrochlorideD22JZE246P40372-00-7PIGYMBULXKLTCJ-UHSSARMYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as triazole ribonucleosides and ribonucleotides. These are nucleoside derivatives containing a ribose (or deoxyribose) moiety which is N-glycosylated to a triazole. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Triazole ribonucleosides and ribonucleotides
Sub Class
Not Available
Direct Parent
Triazole ribonucleosides and ribonucleotides
Alternative Parents
Glycosylamines / Pentoses / Triazoles / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds
show 3 more
Substituents
1,2,4-triazole / Alcohol / Amidine / Aromatic heteromonocyclic compound / Azacycle / Azole / Carboximidamide / Carboxylic acid amidine / Glycosyl compound / Heteroaromatic compound
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
R3B1994K2E
CAS number
119567-79-2
InChI Key
NHKZSTHOYNWEEZ-AFCXAGJDSA-N
InChI
InChI=1S/C8H13N5O4/c9-6(10)7-11-2-13(12-7)8-5(16)4(15)3(1-14)17-8/h2-5,8,14-16H,1H2,(H3,9,10)/t3-,4-,5-,8-/m1/s1
IUPAC Name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboximidamide
SMILES
NC(=N)C1=NN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

References

General References
  1. Schiff ER: Emerging strategies for pegylated interferon combination therapy. Nat Clin Pract Gastroenterol Hepatol. 2007 Jan;4 Suppl 1:S17-21. [Article]
ChemSpider
397669
ChEBI
134989
ChEMBL
CHEMBL2111108
ZINC
ZINC000003781686
PDBe Ligand
R1Y
Wikipedia
Taribavirin
PDB Entries
8db9

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection2
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
2TerminatedTreatmentChronic Hepatitis C Virus (HCV) Infection1

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.2 mg/mLALOGPS
logP-2ALOGPS
logP-2.5Chemaxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.42Chemaxon
pKa (Strongest Basic)5.34Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area150.5 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity77.17 m3·mol-1Chemaxon
Polarizability22.59 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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-05dl-9420000000-51f7cb97d86500c659bf
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9100000000-3a709b3ce53bbb22a286
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0590000000-5561b9ec71385d7f29e2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9630000000-31a744786eae664b42f0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9300000000-db0f61be13000714651e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9500000000-0f6e1b002e24f2f7fc0e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0005-9810000000-69d7b5a09c45087d2131
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-149.5939
predicted
DeepCCS 1.0 (2019)
[M+H]+151.98947
predicted
DeepCCS 1.0 (2019)
[M+Na]+158.90862
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. DNA
Kind
Nucleotide
Organism
Humans
Pharmacological action
Unknown
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
Details2. RNA-directed RNA polymerase L
Kind
Protein
Organism
HPIV-2
Pharmacological action
Unknown
General Function
Rna-directed rna polymerase activity
Specific Function
Displays RNA-directed RNA polymerase, mRNA guanylyl transferase, mRNA (guanine-N(7)-)-methyltransferase and poly(A) synthetase activities. The viral mRNA guanylyl transferase displays a different b...
Gene Name
L
Uniprot ID
P26676
Uniprot Name
RNA-directed RNA polymerase L
Molecular Weight
256380.115 Da
Details3. Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
By generating PPi, plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. PPi inhibits mineralization by binding to nascent hydroxyapat...
Gene Name
ENPP1
Uniprot ID
P22413
Uniprot Name
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
Molecular Weight
104923.58 Da
Details4. RNA-directed RNA polymerase catalytic subunit
Kind
Protein
Organism
Influenza A virus (strain A/Beijing/11/1956 H1N1)
Pharmacological action
Unknown
General Function
Rna-directed rna polymerase activity
Specific Function
RNA-dependent RNA polymerase which is responsible for replication and transcription of virus RNA segments. The transcription of viral mRNAs occurs by a unique mechanism called cap-snatching. 5' met...
Gene Name
PB1
Uniprot ID
P16502
Uniprot Name
RNA-directed RNA polymerase catalytic subunit
Molecular Weight
86534.5 Da
Details5. Cytosolic purine 5'-nucleotidase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nucleotide binding
Specific Function
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-mo...
Gene Name
NT5C2
Uniprot ID
P49902
Uniprot Name
Cytosolic purine 5'-nucleotidase
Molecular Weight
64969.2 Da
Details6. Inosine-5'-monophosphate dehydrogenase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Rna binding
Specific Function
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore pl...
Gene Name
IMPDH1
Uniprot ID
P20839
Uniprot Name
Inosine-5'-monophosphate dehydrogenase 1
Molecular Weight
55405.365 Da

Drug created at March 19, 2008 16:29 / Updated at February 21, 2021 18:52