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
AInosine-5'-monophosphate dehydrogenase 1	inhibitor	Humans
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

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.

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

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Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data
3	Completed	Treatment	Chronic Hepatitis C Virus (HCV) Infection	2	somestatus	stop reason	just information to hide
2	Completed	Treatment	Chronic Hepatitis C Virus (HCV) Infection	1	somestatus	stop reason	just information to hide
2	Terminated	Treatment	Chronic Hepatitis C Virus (HCV) Infection	1	somestatus	stop reason	just information to hide

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	splash10-05dl-9420000000-51f7cb97d86500c659bf
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0002-9100000000-3a709b3ce53bbb22a286
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-0590000000-5561b9ec71385d7f29e2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0002-9630000000-31a744786eae664b42f0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-9300000000-db0f61be13000714651e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-9500000000-0f6e1b002e24f2f7fc0e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0005-9810000000-69d7b5a09c45087d2131
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[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. Inosine-5'-monophosphate dehydrogenase 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General 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 plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors
Specific Function: DNA binding
Gene Name: IMPDH1
Uniprot ID: P20839
Uniprot Name: Inosine-5'-monophosphate dehydrogenase 1
Molecular Weight: 55405.365 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details2. 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.

Details3. RNA-directed RNA polymerase L

Kind: Protein
Organism: HPIV-2
Pharmacological action: Unknown

General Function: RNA-directed RNA polymerase that catalyzes the transcription of viral mRNAs, their capping and polyadenylation. The template is composed of the viral RNA tightly encapsidated by the nucleoprotein (N). The viral polymerase binds to the genomic RNA at the 3' leader promoter, and transcribes subsequently all viral mRNAs with a decreasing efficiency. The first gene is the most transcribed, and the last the least transcribed. The viral phosphoprotein acts as a processivity factor. Capping is concommitant with initiation of mRNA transcription. Indeed, a GDP polyribonucleotidyl transferase (PRNTase) adds the cap structure when the nascent RNA chain length has reached few nucleotides. Ribose 2'-O methylation of viral mRNA cap precedes and facilitates subsequent guanine-N-7 methylation, both activities being carried by the viral polymerase. Polyadenylation of mRNAs occur by a stuttering mechanism at a slipery stop site present at the end viral genes. After finishing transcription of a mRNA, the polymerase can resume transcription of the downstream gene.
Specific Function: ATP binding
Gene Name: L
Uniprot ID: P26676
Uniprot Name: RNA-directed RNA polymerase L
Molecular Weight: 256380.115 Da

Details4. Ectonucleotide pyrophosphatase/phosphodiesterase family member 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Nucleotide pyrophosphatase that generates diphosphate (PPi) and functions in bone mineralization and soft tissue calcification by regulating pyrophosphate levels (By similarity). PPi inhibits bone mineralization and soft tissue calcification by binding to nascent hydroxyapatite crystals, thereby preventing further growth of these crystals (PubMed:11004006). Preferentially hydrolyzes ATP, but can also hydrolyze other nucleoside 5' triphosphates such as GTP, CTP and UTP to their corresponding monophosphates with release of pyrophosphate, as well as diadenosine polyphosphates, and also 3',5'-cAMP to AMP (PubMed:25344812, PubMed:27467858, PubMed:28011303, PubMed:35147247, PubMed:8001561). May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling (PubMed:27467858, PubMed:8001561). Inhibits ectopic joint calcification and maintains articular chondrocytes by repressing hedgehog signaling; it is however unclear whether hedgehog inhibition is direct or indirect (By similarity). Appears to modulate insulin sensitivity and function (PubMed:10615944). Also involved in melanogenesis (PubMed:28964717). Also able to hydrolyze 2',3'-cGAMP (cyclic GMP-AMP), a second messenger that activates TMEM173/STING and triggers type-I interferon production (PubMed:25344812). 2',3'-cGAMP degradation takes place in the lumen or extracellular space, and not in the cytosol where it is produced; the role of 2',3'-cGAMP hydrolysis is therefore unclear (PubMed:25344812). Not able to hydrolyze the 2',3'-cGAMP linkage isomer 3'-3'-cGAMP (PubMed:25344812)
Specific Function: 3',5'-cyclic-AMP phosphodiesterase activity
Gene Name: ENPP1
Uniprot ID: P22413
Uniprot Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
Molecular Weight: 104923.58 Da

Details5. RNA-directed RNA polymerase catalytic subunit

Kind: Protein
Organism: Influenza A virus (strain A/Beijing/11/1956 H1N1)
Pharmacological action: Unknown

General 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' methylated caps of cellular mRNAs are cleaved after 10-13 nucleotides by PA. In turn, these short capped RNAs are used as primers by PB1 for transcription of viral mRNAs. During virus replication, PB1 initiates RNA synthesis and copy vRNA into complementary RNA (cRNA) which in turn serves as a template for the production of more vRNAs.
Specific Function: nucleotide binding
Gene Name: PB1
Uniprot ID: P16502
Uniprot Name: RNA-directed RNA polymerase catalytic subunit
Molecular Weight: 86534.5 Da

Details6. Cytosolic purine 5'-nucleotidase

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Broad specificity cytosolic 5'-nucleotidase that catalyzes the dephosphorylation of 6-hydroxypurine nucleoside 5'-monophosphates (PubMed:10092873, PubMed:12907246, PubMed:1659319, PubMed:9371705). In addition, possesses a phosphotransferase activity by which it can transfer a phosphate from a donor nucleoside monophosphate to an acceptor nucleoside, preferably inosine, deoxyinosine and guanosine (PubMed:1659319, PubMed:9371705). Has the highest activities for IMP and GMP followed by dIMP, dGMP and XMP (PubMed:10092873, PubMed:12907246, PubMed:1659319, PubMed:9371705). Could also catalyze the transfer of phosphates from pyrimidine monophosphates but with lower efficiency (PubMed:1659319, PubMed:9371705). Through these activities regulates the purine nucleoside/nucleotide pools within the cell (PubMed:10092873, PubMed:12907246, PubMed:1659319, PubMed:9371705)
Specific Function: 5'-nucleotidase activity
Gene Name: NT5C2
Uniprot ID: P49902
Uniprot Name: Cytosolic purine 5'-nucleotidase
Molecular Weight: 64969.2 Da

Drug created at March 19, 2008 16:29 / Updated at August 26, 2024 19:23

Taribavirin

Identification

Structure for Taribavirin (DB06408)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References