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
UDNA	Not Available	Humans
URNA-directed RNA polymerase L	Not Available	HPIV-2
UEctonucleotide pyrophosphatase/phosphodiesterase family member 1	Not Available	Humans
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

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.

Drug	Interaction
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Adenovirus 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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Food Interactions

Not Available

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Taribavirin hydrochloride	D22JZE246P	40372-00-7	PIGYMBULXKLTCJ-UHSSARMYSA-N

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
PDBe Ligand: R1Y
Wikipedia: Taribavirin

PDB Entries

8db9

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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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

Taribavirin

Identification

Structure for Taribavirin (DB06408)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets