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
Structure for Taribavirin (DB06408)
- Weight
- Average: 243.223
Monoisotopic: 243.096753919 - Chemical Formula
- C8H13N5O4
- Synonyms
- Ribavirin amidine
- Taribavirin
- Viramidine
- External IDs
- ICN 3142
Pharmacology
- Indication
Investigated for use/treatment in hepatitis (viral, C).
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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.
Target Actions Organism URNA-directed RNA polymerase catalytic subunit Not Available Influenza A virus (strain A/Beijing/11/1956 H1N1) UCytosolic purine 5'-nucleotidase Not Available Humans UInosine-5'-monophosphate dehydrogenase 1 Not Available Humans UDNA Not Available Humans URNA-directed RNA polymerase L Not Available HPIV-2 UEctonucleotide pyrophosphatase/phosphodiesterase family member 1 Not Available Humans - 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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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAdenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Taribavirin. Anthrax vaccine The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Taribavirin. Bacillus calmette-guerin substrain connaught live antigen The 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 antigen The 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 antigen The therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Taribavirin. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Taribavirin. Human adenovirus e serotype 4 strain cl-68578 antigen The therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Taribavirin. Rubella virus vaccine The therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Taribavirin. Typhoid Vaccine Live The therapeutic efficacy of Typhoid Vaccine Live can be decreased when used in combination with Taribavirin. Varicella zoster vaccine (live/attenuated) The therapeutic efficacy of Varicella zoster vaccine (live/attenuated) can be decreased when used in combination with Taribavirin. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Taribavirin hydrochloride D22JZE246P 40372-00-7 PIGYMBULXKLTCJ-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
- Schiff ER: Emerging strategies for pegylated interferon combination therapy. Nat Clin Pract Gastroenterol Hepatol. 2007 Jan;4 Suppl 1:S17-21. [Article]
- External Links
- ChemSpider
- 397669
- ChEBI
- 134989
- ChEMBL
- CHEMBL2111108
- ZINC
- ZINC000003781686
- Wikipedia
- Taribavirin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Chronic Hepatitis C Virus (HCV) Infection 2 2 Completed Treatment Chronic Hepatitis C Virus (HCV) Infection 1 2 Terminated Treatment Chronic Hepatitis C Virus (HCV) Infection 1
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
Property Value Source Water Solubility 11.2 mg/mL ALOGPS logP -2 ALOGPS logP -2.5 ChemAxon logS -1.3 ALOGPS pKa (Strongest Acidic) 12.42 ChemAxon pKa (Strongest Basic) 5.34 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 150.5 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 77.17 m3·mol-1 ChemAxon Polarizability 22.59 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
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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
- 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
Unknown
- 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
- 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
Drug created on March 19, 2008 16:29 / Updated on February 21, 2021 18:52