Page last updated: 2024-12-07

ribavirin 5'-diphosphate

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Description

Ribavirin 5'-diphosphate is a nucleotide analog that inhibits the activity of the viral enzyme inosine monophosphate dehydrogenase (IMPDH). IMPDH is responsible for the synthesis of guanine nucleotides, which are essential for viral replication. By inhibiting IMPDH, ribavirin 5'-diphosphate reduces the production of guanine nucleotides, thereby inhibiting viral replication. Ribavirin 5'-diphosphate has been shown to be effective against a variety of viruses, including hepatitis C virus (HCV), respiratory syncytial virus (RSV), and influenza virus. The compound has also been studied for its potential use in the treatment of cancer. Ribavirin 5'-diphosphate is synthesized by phosphorylation of ribavirin, a nucleoside analog that is also used as an antiviral drug. The synthesis of ribavirin 5'-diphosphate involves a multi-step process that utilizes enzymes and chemical reagents to convert ribavirin to its diphosphate form. The compound is studied because of its potential to inhibit viral replication and its possible use in the treatment of cancer. Ribavirin 5'-diphosphate is an important compound because it may provide new avenues for the development of antiviral and anticancer therapies.'

ribavirin-5'-phosphate: RN given refers to 5'-phosphate cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ribavirin 5'-monophosphate : A 1-ribosyltriazole that is ribavirin in which the hydroxy group at the 5'-position is replaced by a phosphonooxy group. It is the active metabolite of the antiviral agent ribavirin. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ribavirin 5'-diphosphate : A 1-ribosyltriazole that is ribavirin in which the hydroxy group at the 5'-position is replaced by a diphosphate group. It is the metabolite of the antiviral agent ribavirin. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID100252
CHEMBL ID1235764
CHEBI ID45490
SCHEMBL ID10882076
MeSH IDM0157239
PubMed CID124970
CHEMBL ID3306225
CHEBI ID180481
MeSH IDM0157239

Synonyms (46)

Synonym
CHEMBL1235764
1h-1,2,4-triazole-3-carboxamide, 1-(5-o-phosphono-.beta.-d-ribofuranosyl)-
[(2r,3s,4r,5r)-5-(3-carbamoyl-1,2,4-triazol-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
icn 3847
nsc274937
ribavirin-5'-monophosphate
ribavirin 5'-p
40925-28-8
RVP ,
ribavirin monophosphate
nsc-274937
1h-1,2,4-triazole-3-carboxamide, 1-(5-o-phosphono-beta-d-ribofuranosyl)- (9ci)
ribavirin-5'-phosphate
1beta-d-ribofuranosyl-1,2,4-triazole-3-carboxamide-5'-phosphate
1-(5-o-phosphono-beta-d-ribofuranosyl)-1h-1,2,4-triazole-3-carboxamide
1h-1,2,4-triazole-3-carboxamide, 1-(5-o-phosphono-beta-d-ribofuranosyl)-
virazole 5'-phosphate
ribavirin 5'-monophosphate
ribavirin 5'-phosphate
1ME7
1ME8
nsc 274937
unii-o9fvv27p11
o9fvv27p11 ,
1-.beta.-d-ribofuranosyl-1,2,4-triazole-3-carboxamide-5'-phosphate
SCHEMBL10882076
DTXSID20193928
DB14663
Q27285517
ribavirin-mp
CHEBI:45490
rbv-mp
ribavirin-dp
63142-70-1
CHEBI:180481
ribavirin diphosphate
1-{5-o-[hydroxy(phosphonooxy)phosphoryl]-beta-d-ribofuranosyl}-1h-1,2,4-triazole-3-carboxamide
[5-(3-carbamoyl(1,2,4-triazolyl))-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
[(2r,3s,4r,5r)-5-(3-carbamoyl-1,2,4-triazol-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl phosphono hydrogen phosphate
rdp
ribavirin 5'-diphosphate
[(2r,3s,4r,5r)-5-(3-carbamoyl-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono hydrogen phosphate
1h-1,2,4-triazole-3-carboxamide, 1-(5-o-(hydroxy(phosphonooxy)phosphinyl)-beta-d-ribofuranosyl)-
ribavirin 5'-diphosphate lithium salt
CHEMBL3306225
DTXSID00212489
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
human blood serum metaboliteAny metabolite (endogenous or exogenous) found in human blood serum samples.
drug metabolitenull
antiviral agentA substance that destroys or inhibits replication of viruses.
EC 1.1.1.205 (IMP dehydrogenase) inhibitorAn EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of IMP dehydrogenase (EC 1.1.1.205), so blocking de novo biosynthesis of purine nucleotides.
antiviral agentA substance that destroys or inhibits replication of viruses.
drug metabolitenull
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (6)

ClassDescription
1-ribosyltriazoleA 1-glycosyltriazole in which the glycosyl residue is specified as ribosyl.
ribose monophosphate
aromatic amideAn amide in which the amide linkage is bonded directly to an aromatic system.
monocarboxylic acid amideA carboxamide derived from a monocarboxylic acid.
primary carboxamideA carboxamide resulting from the formal condensation of a carboxylic acid with ammonia; formula RC(=O)NH2.
1-ribosyltriazoleA 1-glycosyltriazole in which the glycosyl residue is specified as ribosyl.
aromatic amideAn amide in which the amide linkage is bonded directly to an aromatic system.
monocarboxylic acid amideA carboxamide derived from a monocarboxylic acid.
primary carboxamideA carboxamide resulting from the formal condensation of a carboxylic acid with ammonia; formula RC(=O)NH2.
ribose diphosphate
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Inosine-5'-monophosphate DehydrogenaseTritrichomonas suisKi0.06500.06500.06500.0650AID977610
Chain A, Inosine-5'-monophosphate DehydrogenaseTritrichomonas suisKi0.06500.06500.06500.0650AID977610
Genome polyprotein IC50 (µMol)250.00000.70001.95673.8000AID240983
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2002The Journal of biological chemistry, Dec-27, Volume: 277, Issue:52
Crystal structure of Tritrichomonas foetus inosine monophosphate dehydrogenase in complex with the inhibitor ribavirin monophosphate reveals a catalysis-dependent ion-binding site.
AID1811Experimentally measured binding affinity data derived from PDB2002The Journal of biological chemistry, Dec-27, Volume: 277, Issue:52
Crystal structure of Tritrichomonas foetus inosine monophosphate dehydrogenase in complex with the inhibitor ribavirin monophosphate reveals a catalysis-dependent ion-binding site.
AID578590Inhibition of GATA4-DNA interaction in HEK293 nuclear extract at 150 uM after 15 mins by EMSA assay2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578592Inhibition of GATA4- DNA interaction in mouse C2C12 cells at 100 uM after 24 hrs by EMSA assay2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID1133197Inhibition of Escherichia coli IMP cyclohydrolase (unknown origin) assessed as ratio of compound concentration for 50% inhibition of enzyme activity to 1.7 to 3 x 10'-5 M of substrate concentration1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID578597Inhibition of GATA4-DNA interaction in HEK293 nuclear extract at 50 to 150 uM after 15 mins by EMSA assay2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578595Lipophilicity, log P of compound2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578589Inhibition of GATA4-DNA interaction in HEK293 nuclear extract at 100 uM after 15 mins by EMSA assay2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID1133195Inhibition of Escherichia coli IMP dehydrogenase assessed as ratio of compound concentration for 50% inhibition of enzyme activity to 1.7 to 3 x 10'-5 M of substrate concentration1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID92599Noncompetitive inhibitory activity against Inosine-5'-monophosphate dehydrogenase using NAD as viable substrate1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Ribavirin, tiazofurin, and selenazofurin: mononucleotides and nicotinamide adenine dinucleotide analogues. Synthesis, structure, and interactions with IMP dehydrogenase.
AID578600Cytotoxicity in mouse C2C12 cells assessed as effect on cell proliferation upto 150 uM2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578593Inhibition of GATA4 in mouse C2C12 cells assessed as myoblast differentiation to myotubes at 100 uM after 48 hrs by immunofluorescence assay in presence of 0.5% FBS relative to control2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578594Inhibition of GATA4 in mouse C2C12 cells assessed as myoblast differentiation to myotubes at 100 uM after 48 hrs by immunofluorescence assay in presence of 20 % FBS relative to control2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578603Cytotoxicity in human HEK293 cells assessed as cell death upto 150 uM2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID92590Competitive Inhibitory activity against Inosine-5'-monophosphate dehydrogenase using IMP as viable substrate1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Ribavirin, tiazofurin, and selenazofurin: mononucleotides and nicotinamide adenine dinucleotide analogues. Synthesis, structure, and interactions with IMP dehydrogenase.
AID578602Cytotoxicity in mouse C2C12 cells assessed as cell death upto 150 uM2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578599Cytotoxicity in human HEK293 cells assessed as effect on cell proliferation upto 150 uM2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578605Effect on NFATc1 in HEK293 nuclear extract at 50 uM after 15 mins by EMSA assay2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID1123337Inhibition of rat spleen IMP dehydrogenase using NAD and IMP up to 1 hr1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Studies on the mechanism of antiviral action of 1-(beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (ribavirin).
AID578591Inhibition of GATA4- mediated BNP promoter activation in HeLa cells at 100 uM after 24 hrs by luciferase reporter gene assay2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578588Inhibition of GATA4-DNA interaction in HEK293 nuclear extract at 50 uM after 15 mins by EMSA assay2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578601Cytotoxicity in human HeLa cells assessed as cell death upto 150 uM2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578598Cytotoxicity in human HeLa cells assessed as effect on cell proliferation upto 150 uM2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578604Effect on Tbx5 in HEK293 nuclear extract at 50 uM after 15 mins by EMSA assay2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID578596Drug uptake in human HeLa cells after 24 hrs2011Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5
Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.
AID1133196Inhibition of Escherichia coli adenylosuccinate synthetase assessed as ratio of compound concentration for 50% inhibition of enzyme activity to 1.7 to 3 x 10'-5 M of substrate concentration1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Synthesis and antiviral and enzymatic studies of certain 3-deazaguanines and their imidazolecarboxamide precursors.
AID152713Cytotoxicity against P388 cells in culture1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Ribavirin, tiazofurin, and selenazofurin: mononucleotides and nicotinamide adenine dinucleotide analogues. Synthesis, structure, and interactions with IMP dehydrogenase.
AID240983Inhibitory concentration against hepatitis C virus helicase2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
Control of hepatitis C: a medicinal chemistry perspective.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (52.94)18.7374
1990's1 (5.88)18.2507
2000's3 (17.65)29.6817
2010's4 (23.53)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.88

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.88 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.88)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]