Compounds > 4'-azidocytidine
Page last updated: 2024-12-08

4'-azidocytidine

Description

4'-azidocytidine: antiviral; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID457388
CHEMBL ID393857
CHEBI ID195574
MeSH IDM0496337

Synonyms (27)

Synonym
HY-10444
478182-28-4
4'-azidocytidine
4-amino-1-[(2r,3r,4s,5r)-5-azido-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
R1479 ,
4'azc
CHEMBL393857
r-1479
CHEBI:195574
4-amino-1-[(2r,3r,4s,5r)-5-azido-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
CS-0362
DTXSID80332457
M71RA9DMGJ ,
4'-c-azidocytidine
4-amino-1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-5-((imino-$l^5-azanylidene)amino)tetrahydrofuran-2-yl)pyrimidin-2-one
cytidine, 4'-c-azido-
4-amino-1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-5-((imino-lambda5-azanylidene)amino)tetrahydrofuran-2-yl)pyrimidin-2-one
unii-m71ra9dmgj
r 1479
4-amino-1-((2r,3r,4s,5r)-5-azido-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1h)-one
Q27283571
4-amino-1-((2r,3r,4s,5r)-5-azido-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1h)-one
A847966
F83782
AS-56761
4-amino-1-[(2r,3r,4s,5r)-5-azido-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
AKOS037645067

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Some have hypothesized that the active metabolites of toxic ribonucleoside analogs, the triphosphate forms, inadvertently target human mitochondrial RNA polymerase (POLRMT), thus inhibiting mitochondrial RNA transcription and protein synthesis."( Structure-activity relationship analysis of mitochondrial toxicity caused by antiviral ribonucleoside analogs.
Behera, I; Beigelman, L; Chaudhuri, S; Deval, J; Dyatkina, N; Jekle, A; Jin, Z; Kinkade, A; Rajwanshi, VK; Smith, DB; Symons, JA; Tucker, K; Wang, G, 2017)		0.46
"This study concluded that FNC is safe to use though higher concentration shows slight toxicity."( Safety Assessment of a Nucleoside Analogue FNC (2'-deoxy-2'- β-fluoro-4'-azidocytidine ) in Balb/c Mice: Acute Toxicity Study.
Acharya, A; Delu, V; Fayzullina, D; Kaushalendra, K; Kumar, N; Kumar, S; Mohanta, SP; Patel, AK; Rachana, K; Shukla, A; Singh, RK; Tiwari, R; Ulasov, I; Yadav, L, 2023)		1.14

Pharmacokinetics

ExcerptReferenceRelevance
" The present study was undertaken to evaluate the absolute oral bioavailability of FNC in rats and the pharmacokinetic properties of FNC after intragastric administration of single and multiple doses in rats and dogs."( Quantification of 2'-deoxy-2'-β-fluoro-4'-azidocytidine in rat and dog plasma using liquid chromatography-quadrupole time-of-flight and liquid chromatography-triple quadrupole mass spectrometry: Application to bioavailability and pharmacokinetic studies.
Chang, J; Chen, X; Cheng, T; Dong, L; Guo, M; Guo, X; Jiang, J; Peng, Y; Wang, Q; Zhang, J; Zhang, Y, 2014)		0.67

Compound-Compound Interactions

ExcerptReferenceRelevance
" The present study evaluated the efficacy and safety of R1626 administered for 4 weeks in combination with peginterferon alfa-2a +/- ribavirin in HCV genotype 1-infected treatment-naive patients."( R1626 plus peginterferon Alfa-2a provides potent suppression of hepatitis C virus RNA and significant antiviral synergy in combination with ribavirin.
Chan, A; Everson, GT; Fried, MW; Ghalib, R; Godofsky, E; Harrison, S; Hill, G; Najera, I; Nelson, D; Nyberg, L; Pockros, PJ; Rodriguez-Torres, M; Shiffman, ML, 2008)		0.35
"6 log(10) units was obtained in phase II studies when Debio 025 was combined with interferon (R."( Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
Coelmont, L; Dumont, JM; Kaptein, S; Neyts, J; Paeshuyse, J; Vliegen, I; Vuagniaux, G, 2009)		0.35

Bioavailability

ExcerptReferenceRelevance
" R1626, a tri-isobutyl ester prodrug of R1479, was developed to increase bioavailability and improve antiviral activity."( Robust antiviral activity of R1626, a novel nucleoside analog: a randomized, placebo-controlled study in patients with chronic hepatitis C.
Berns, H; Cooksley, G; Dore, GJ; Hill, G; Klumpp, K; Najera, I; Roberts, SK; Robson, R; Shaw, D; Washington, C, 2008)		0.35
" The present study was undertaken to evaluate the absolute oral bioavailability of FNC in rats and the pharmacokinetic properties of FNC after intragastric administration of single and multiple doses in rats and dogs."( Quantification of 2'-deoxy-2'-β-fluoro-4'-azidocytidine in rat and dog plasma using liquid chromatography-quadrupole time-of-flight and liquid chromatography-triple quadrupole mass spectrometry: Application to bioavailability and pharmacokinetic studies.
Chang, J; Chen, X; Cheng, T; Dong, L; Guo, M; Guo, X; Jiang, J; Peng, Y; Wang, Q; Zhang, J; Zhang, Y, 2014)		0.67
" ALS-8176 (71), the 3',5'-di-O-isobutyryl prodrug of 2c, demonstrated good oral bioavailability and a high level of 2c-TP in vivo."( Discovery of 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine (ALS-8176), a first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection.
Beigelman, L; Blatt, LM; Chanda, SM; Deval, J; Dyatkina, N; Fung, A; Hong, J; Jin, Z; Liu, J; Prhavc, M; Serebryany, V; Smith, DB; Stevens, SK; Symons, JA; Tam, Y; Taylor, J; Wang, G; Zhang, Q, 2015)		0.42

Dosage Studied

ExcerptRelevanceReference
" Dosing of R1626 was limited by neutropenia; a study of different dosages of R1626 in combination with peginterferon alfa-2a and ribavirin is underway."( R1626 plus peginterferon Alfa-2a provides potent suppression of hepatitis C virus RNA and significant antiviral synergy in combination with ribavirin.
Chan, A; Everson, GT; Fried, MW; Ghalib, R; Godofsky, E; Harrison, S; Hill, G; Najera, I; Nelson, D; Nyberg, L; Pockros, PJ; Rodriguez-Torres, M; Shiffman, ML, 2008)		0.35
" The oral dosing of 23 led to substantially increased exposure to 5 in both rats and dogs."( 2'-Deoxy-2'-spirocyclopropylcytidine revisited: a new and selective inhibitor of the hepatitis C virus NS5B polymerase.
Berke, JM; Buyck, C; Cummings, MD; de Kock, H; Dillen, LL; Fanning, G; Hu, L; Jonckers, TH; Lachau-Durand, S; Lin, TI; Nilsson, M; Raboisson, P; Rosenquist, A; Rydegård, C; Samuelsson, B; Simmen, K; Sund, C; Van Emelen, K; Van Hoof, S; Vandekerckhove, LA; Vandyck, K; Vijgen, L, 2010)		0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-glycosyl compoundA glycosyl compound arising formally from the elimination of water from a glycosidic hydroxy group and an H atom bound to a nitrogen atom, thus creating a C-N bond.
[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]

Bioassays (62)

Assay IDTitleYearJournalArticle
AID573109Antiviral activity against Hepatitis C virus genotype 1b infected in human Huh-9-13 cells assessed as reduction in replicon RNA after 4days by RT-qPCR analysis2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID536905Antiviral activity against Hepatitis C virus subtype 1b with adaptive mutations of E1202G, T1280I, K1846T in NS5B polymerase infected in human HuH7 cells assessed as inhibition of viral replication after 3 days by luciferase assay2010Journal of medicinal chemistry, Nov-25, Volume: 53, Issue:22
2'-Deoxy-2'-spirocyclopropylcytidine revisited: a new and selective inhibitor of the hepatitis C virus NS5B polymerase.
AID475235Therapeutic index, ratio of CC50 for human HuH7 cells to EC50 for HCV 1b2010Journal of medicinal chemistry, Apr-22, Volume: 53, Issue:8
Synthesis of new acridone derivatives, inhibitors of NS3 helicase, which efficiently and specifically inhibit subgenomic HCV replication.
AID348494Cytotoxicity against human HuH7 cells by XTT assay2008Bioorganic & medicinal chemistry, Oct-01, Volume: 16, Issue:19
New acridone-4-carboxylic acid derivatives as potential inhibitors of hepatitis C virus infection.
AID555947Antiviral activity against HCV genotype 1b infected in human Huh-9-13 cells assessed as reduction in viral replication selected after 5 passages at 4 uM by quantitative RT-PCR relative to wild type virus2009Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3
Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
AID573111Antiviral activity against Hepatitis C virus genotype 1b infected in human Huh-Mono cells assessed as reduction in replicon RNA after 4 days by RT-qPCR analysis2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID1200154Antiviral activity against Respiratory syncytial virus subgenomic replicon system in 395 HeLa cells assessed as reduction in viral replication after 7 days by renilla luciferase assay2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Discovery of 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine (ALS-8176), a first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection.
AID555953Antiviral activity against R479-resistant HCV genotype 1b infected in human Huh-9-13 cells assessed as reduction in viral replication after 3 days by quantitative RT-PCR2009Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3
Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
AID547287Selectivity ratio of EC90 for Hepatitis C virus harboring NS5B polymerase S96T mutant gene to EC90 for HCV harboring wild type NS5B polymerase2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
PSI-7851, a pronucleotide of beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine monophosphate, is a potent and pan-genotype inhibitor of hepatitis C virus replication.
AID514138Antiviral activity against HCV Con 1 by subgenomic replicon assay2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Studies on the anti-hepatitis C virus activity of newly synthesized tropolone derivatives: identification of NS3 helicase inhibitors that specifically inhibit subgenomic HCV replication.
AID353350Cytotoxicity against human 2209-23 cells assessed as cell viability by WST-1 assay2009Journal of medicinal chemistry, May-14, Volume: 52, Issue:9
The design, synthesis, and antiviral activity of monofluoro and difluoro analogues of 4'-azidocytidine against hepatitis C virus replication: the discovery of 4'-azido-2'-deoxy-2'-fluorocytidine and 4'-azido-2'-dideoxy-2',2'-difluorocytidine.
AID475233Antiviral activity against HCV 1b infected in human HuH7 cells assessed as inhibition of viral RNA replication after 4 days by replicon assay2010Journal of medicinal chemistry, Apr-22, Volume: 53, Issue:8
Synthesis of new acridone derivatives, inhibitors of NS3 helicase, which efficiently and specifically inhibit subgenomic HCV replication.
AID547286Antiviral activity against Hepatitis C virus harboring NS5B polymerase S96T mutant gene infected in human lunet cells by luciferase-based replicon assay2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
PSI-7851, a pronucleotide of beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine monophosphate, is a potent and pan-genotype inhibitor of hepatitis C virus replication.
AID520336Cytotoxicity against human HuH7 cells2008Antimicrobial agents and chemotherapy, May, Volume: 52, Issue:5
The hepatitis C virus replicon presents a higher barrier to resistance to nucleoside analogs than to nonnucleoside polymerase or protease inhibitors.
AID411722Cytotoxicity against human 2209-23 cells by WST1 cell ciability assay2009Journal of medicinal chemistry, Jan-08, Volume: 52, Issue:1
The design, synthesis, and antiviral activity of 4'-azidocytidine analogues against hepatitis C virus replication: the discovery of 4'-azidoarabinocytidine.
AID573112Cytotoxicity against human Huh5-2 cells after 3 days by MTT assay2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID348493Antiviral activity against HCV subtype 1a in Huh7 cells assessed as reduction of viral RNA replication2008Bioorganic & medicinal chemistry, Oct-01, Volume: 16, Issue:19
New acridone-4-carboxylic acid derivatives as potential inhibitors of hepatitis C virus infection.
AID573106Cytotoxicity against human Huh-9-13 cells after 3 days by MTT assay2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID306693Cytotoxicity against human 2209-23 cells at 20 uM2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479.
AID555946Antiviral activity against HCV genotype 1b infected in human Huh-9-13 cells assessed as reduction in viral replication selected after 7 passages at 15 uM by quantitative RT-PCR relative to wild type virus2009Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3
Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
AID555948Antiviral activity against HCV genotype 1b infected in human Huh-9-13 cells assessed as reduction in viral replication selected at 0.5 uM by quantitative RT-PCR2009Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3
Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
AID125167In vitro Cytotoxic concentration in mock-infected A3.01 cells.1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID353351Antiproliferative activity against human 2209-23 cells assessed as [3H]thymidine incorporation by scintillation proximity assay2009Journal of medicinal chemistry, May-14, Volume: 52, Issue:9
The design, synthesis, and antiviral activity of monofluoro and difluoro analogues of 4'-azidocytidine against hepatitis C virus replication: the discovery of 4'-azido-2'-deoxy-2'-fluorocytidine and 4'-azido-2'-dideoxy-2',2'-difluorocytidine.
AID547285Antiviral activity against Hepatitis C virus harboring wild-type NS5B infected in human lunet cells by luciferase-based replicon assay2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
PSI-7851, a pronucleotide of beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine monophosphate, is a potent and pan-genotype inhibitor of hepatitis C virus replication.
AID306696Cytotoxicity against human 2209-23 cells2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479.
AID306697Cytostatic activity against human 2209-23 cells2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479.
AID547283Antiviral activity against Hepatitis C virus harboring NS5B polymerase S282T mutant gene infected in human HuH7 cells by luciferase-based replicon assay2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
PSI-7851, a pronucleotide of beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine monophosphate, is a potent and pan-genotype inhibitor of hepatitis C virus replication.
AID555955Antiviral activity against VX 950-resistant HCV genotype 1b infected in human Huh-9-13 cells assessed as reduction in viral replication after 3 days by quantitative RT-PCR2009Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3
Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
AID573107Cytotoxicity against human Huh-Mono cells after 3 days by MTT assay2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID536906Cytotoxicity against human HuH7 cells expressing CMV-Luc after 3 days by luciferase assay2010Journal of medicinal chemistry, Nov-25, Volume: 53, Issue:22
2'-Deoxy-2'-spirocyclopropylcytidine revisited: a new and selective inhibitor of the hepatitis C virus NS5B polymerase.
AID555945Antiviral activity against HCV genotype 1b infected in human Huh-9-13 cells assessed as reduction in viral replication selected after 5 passages at 4 uM by quantitative RT-PCR2009Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3
Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
AID306698Inhibition of HCV 1b BK NS5B570 RNA polymerase2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479.
AID573110Antiviral activity against Hepatitis C virus genotype 1b infected in human HuH6 cells assessed as reduction in replicon RNA after 4days by RT-qPCR analysis2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID547090Antiviral activity against Hepatitis C virus harboring NS5B polymerase S96T/N142T mutant gene infected in human HuH7 cells by luciferase-based replicon assay2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
PSI-7851, a pronucleotide of beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine monophosphate, is a potent and pan-genotype inhibitor of hepatitis C virus replication.
AID7700Compound was tested in vitro for inhibition of cytopathogenicity of LAV(IIIB) in CD4+ T-cells (A3.01); Not active1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID1497242Antiviral activity against Dengue virus 2 infected in human PBMC after 24 hrs post infection by plaque assay2018Bioorganic & medicinal chemistry letters, 07-15, Volume: 28, Issue:13
Structure-activity relationship of uridine-based nucleoside phosphoramidate prodrugs for inhibition of dengue virus RNA-dependent RNA polymerase.
AID514139Cytotoxicity against human HuH7 cells2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Studies on the anti-hepatitis C virus activity of newly synthesized tropolone derivatives: identification of NS3 helicase inhibitors that specifically inhibit subgenomic HCV replication.
AID555954Antiviral activity against BILN 2061-resistant HCV genotype 1b infected in human Huh-9-13 cells assessed as reduction in viral replication after 3 days by quantitative RT-PCR2009Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3
Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
AID411723Antiproliferative activity against human 2209-23 cells by [3H]thymidine incorporation scintillation proximity assay2009Journal of medicinal chemistry, Jan-08, Volume: 52, Issue:1
The design, synthesis, and antiviral activity of 4'-azidocytidine analogues against hepatitis C virus replication: the discovery of 4'-azidoarabinocytidine.
AID306695Antiviral activity against HCV 1b replicon in human 2209-23 cells2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479.
AID658633Competitive inhibition of Hepatitis C virus NS5B RNA-dependent RNA polymerase2012Bioorganic & medicinal chemistry, May-15, Volume: 20, Issue:10
Hepatitis C RNA-dependent RNA polymerase inhibitors: a review of structure-activity and resistance relationships; different scaffolds and mutations.
AID428151Antiviral activity against HCV Con1 GT1b by replicon assay2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
The application of phosphoramidate ProTide technology to the potent anti-HCV compound 4'-azidocytidine (R1479).
AID353349Antiviral activity against HCV 1b infected in human 2209-23 cells by replicon assay2009Journal of medicinal chemistry, May-14, Volume: 52, Issue:9
The design, synthesis, and antiviral activity of monofluoro and difluoro analogues of 4'-azidocytidine against hepatitis C virus replication: the discovery of 4'-azido-2'-deoxy-2'-fluorocytidine and 4'-azido-2'-dideoxy-2',2'-difluorocytidine.
AID573105Cytotoxicity against human HuH6 cells after 3 days by MTT assay2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID573108Antiviral activity against Hepatitis C virus genotype 1b infected in human Huh5-2 cells assessed as reduction in replicon RNA after 4 days by luciferase assay2008Antimicrobial agents and chemotherapy, Sep, Volume: 52, Issue:9
Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.
AID555949Antiviral activity against HCV genotype 1b infected in human Huh-9-13 cells assessed as reduction in viral replication selected at 0.1 uM by quantitative RT-PCR2009Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3
Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
AID555944Antiviral activity against HCV genotype 1b infected in human Huh-9-13 cells assessed as reduction in viral replication selected after 7 passages at 15 uM by quantitative RT-PCR2009Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3
Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
AID547284Selectivity ratio of EC90 for Hepatitis C virus harboring NS5B polymerase S282T mutant gene to EC90 for Hepatitis C virus harboring wild-type NS5B polymerase2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
PSI-7851, a pronucleotide of beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine monophosphate, is a potent and pan-genotype inhibitor of hepatitis C virus replication.
AID555950Antiviral activity against compound-resistant HCV genotype 1b infected in human Huh-9-13 cells assessed as reduction in viral replication after 3 days by quantitative RT-PCR2009Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3
Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
AID1200155Cytotoxicity against human HeLa cells assessed as cell viability by CellTiter-Glo luminescent assay2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Discovery of 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine (ALS-8176), a first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection.
AID411721Antiviral activity against Hepatitis C virus infected human 2209-23 cells by genotype 1b replicon assay2009Journal of medicinal chemistry, Jan-08, Volume: 52, Issue:1
The design, synthesis, and antiviral activity of 4'-azidocytidine analogues against hepatitis C virus replication: the discovery of 4'-azidoarabinocytidine.
AID475234Cytotoxicity against human HuH7 cells after3 days by MTT assay2010Journal of medicinal chemistry, Apr-22, Volume: 53, Issue:8
Synthesis of new acridone derivatives, inhibitors of NS3 helicase, which efficiently and specifically inhibit subgenomic HCV replication.
AID555951Antiviral activity against cyclosporine-resistant HCV genotype 1b infected in human Huh-9-13 cells assessed as reduction in viral replication after 3 days by quantitative RT-PCR2009Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3
Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
AID1497244Inhibition of human full length POLRMT using 32P-RNA primer/DNA template assessed as single nucleotide incorporation rate at 500 uM by SDS-PAGE analysis relative to CTP2018Bioorganic & medicinal chemistry letters, 07-15, Volume: 28, Issue:13
Structure-activity relationship of uridine-based nucleoside phosphoramidate prodrugs for inhibition of dengue virus RNA-dependent RNA polymerase.
AID520335Antiviral activity against Hepatitis C virus subtype 1b Con1 infected in human HuH7 cells after 3 days by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, May, Volume: 52, Issue:5
The hepatitis C virus replicon presents a higher barrier to resistance to nucleoside analogs than to nonnucleoside polymerase or protease inhibitors.
AID571733Antiviral activity against Hepatitis C virus infected in cells assessed as log reduction in viral RNA level from baseline at 4500 mg administered BID for 14 days by Replicon Assays2008Antimicrobial agents and chemotherapy, Dec, Volume: 52, Issue:12
1,5-benzodiazepines, a novel class of hepatitis C virus polymerase nonnucleoside inhibitors.
AID555952Antiviral activity against 2'-C-methyl-2'-fluoro-cytidine-resistant HCV genotype 1b infected in human Huh-9-13 cells assessed as reduction in viral replication after 3 days by quantitative RT-PCR2009Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3
Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.
AID125169In vitro Cytotoxic concentration in mock-infected A3.01 cells - 100% toxicity.1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID547282Antiviral activity against Hepatitis C virus harboring wild-type NS5B infected in human HuH7 cells by luciferase-based replicon assay2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
PSI-7851, a pronucleotide of beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine monophosphate, is a potent and pan-genotype inhibitor of hepatitis C virus replication.
AID306691Antiviral activity against HCV 1b replicon in human 2209-23 cells assessed as inhibition of viral replication at 20 uM2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479.
AID353348Inhibition of HCV NS5B polymerase-mediated RNA synthesis2009Journal of medicinal chemistry, May-14, Volume: 52, Issue:9
The design, synthesis, and antiviral activity of monofluoro and difluoro analogues of 4'-azidocytidine against hepatitis C virus replication: the discovery of 4'-azido-2'-deoxy-2'-fluorocytidine and 4'-azido-2'-dideoxy-2',2'-difluorocytidine.
AID536907Cytotoxicity against human MT4 cells expressing LTR-Luc after 3 days by luciferase assay2010Journal of medicinal chemistry, Nov-25, Volume: 53, Issue:22
2'-Deoxy-2'-spirocyclopropylcytidine revisited: a new and selective inhibitor of the hepatitis C virus NS5B polymerase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (3.03)18.2507
2000's18 (54.55)29.6817
2010's13 (39.39)24.3611
2020's1 (3.03)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (6.06%)5.53%
Reviews3 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other28 (84.85%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
indole
[no description available]		2.0410indole;
polycyclic heteroarene		Escherichia coli metabolite
4,5,6,7-tetrabromo-2-azabenzimidazole
4,5,6,7-tetrabromobenzotriazole: a CK2 kinase inhibitor		2.0410
uridine
[no description available]		2.0310uridinesdrug metabolite;
fundamental metabolite;
human metabolite
cytidine
[no description available]		7.86182cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
cytarabine
[no description available]		2.0510beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
benzofuran
benzofuran: RN & structure given in first source. 1-benzofuran : A benzofuran consisting of fused benzene and furan rings. It is the parent compound of the class of 1-benzofurans.		2.04101-benzofurans;
benzofuran
pyrazines
Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.		2.1510diazine;
pyrazines		Daphnia magna metabolite
thiophene-2-carboxylate
thiophene-2-carboxylic acid : A thiophenecarboxylic acid in which the carboxy group is located at position 2.		2.0410thiophenecarboxylic acid
deoxycytidine
[no description available]		340pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
arabinofuranosylcytosine triphosphate
Arabinofuranosylcytosine Triphosphate: A triphosphate nucleotide analog which is the biologically active form of CYTARABINE. It inhibits nuclear DNA synthesis.		2.1110
azides
Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.		2.0510pseudohalide anionmitochondrial respiratory-chain inhibitor
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		1.9810azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
ribavirin
Rebetron: Rebetron is tradename		5.63511-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
lamivudine
[no description available]		2.110monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		2.1510adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
4'-azidothymidine
4'-azidothymidine: inhibits HIV replication in human lymphocytes		1.9810
2'-fluoro-2'-deoxycytidine
[no description available]		2.0310
2',2'-difluorodeoxycytidine 5'-triphosphate
[no description available]		2.1110pyrimidone
proline
Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.		4.0520amino acid zwitterion;
glutamine family amino acid;
L-alpha-amino acid;
proline;
proteinogenic amino acid		algal metabolite;
compatible osmolytes;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
3'-deoxycytidine
[no description available]		3.1710
2'-o-methylcytidine
[no description available]		3.1710methylcytidine
3'-deoxycytidine 5'-triphosphate
[no description available]		2.0510
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		3.1310
aphidicolin
Aphidicolin: An antiviral antibiotic produced by Cephalosporium aphidicola and other fungi. It inhibits the growth of eukaryotic cells and certain animal viruses by selectively inhibiting the cellular replication of DNA polymerase II or the viral-induced DNA polymerases. The drug may be useful for controlling excessive cell proliferation in patients with cancer, psoriasis or other dermatitis with little or no adverse effect upon non-multiplying cells.. aphidicolin : A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.		2.0510tetracyclic diterpenoidantimicrobial agent;
antimitotic;
antineoplastic agent;
antiviral drug;
apoptosis inducer;
Aspergillus metabolite;
DNA synthesis inhibitor;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
fungal metabolite
favipiravir
favipiravir : A member of the class of pyrazines that is pyrazine substituted by aminocarbonyl, hydroxy and fluoro groups at positions 2, 3 and 6, respectively. It is an anti-viral agent that inhibits RNA-dependent RNA polymerase of several RNA viruses and is approved for the treatment of influenza in Japan.		2.1510hydroxypyrazine;
organofluorine compound;
primary carboxamide		anticoronaviral agent;
antiviral drug;
EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor
2'-c-methyladenosine
2'-C-methyladenosine: antiviral		3.5620
2'-c-methylcytidine
2'-C-methylcytidine: structure in first source		3.2960
telaprevir
[no description available]		4.0640cyclopentapyrrole;
cyclopropanes;
oligopeptide;
pyrazines		antiviral drug;
hepatitis C protease inhibitor;
peptidomimetic
cyclosporine
ramihyphin A: one of the metabolites produced by Fusarium sp. S-435; RN given refers to cpd with unknown MF		2.4520homodetic cyclic peptideanti-asthmatic drug;
anticoronaviral agent;
antifungal agent;
antirheumatic drug;
carcinogenic agent;
dermatologic drug;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
geroprotector;
immunosuppressive agent;
metabolite
psi 6130
2'-deoxy-2'-fluoro-2'-C-methylcytidine: PSI-6130 is the (beta-D)-isomer; has antiviral activity against hepatitis C virus; structure in first source		2.9640
valopicitabine
valopicitabine: prodrug of 2'-C-methylcytidine; an anti-hepatitis C virus agent; structure in first source		3.8330
biln 2061
BILN 2061: a macrocyclic NS3 protease inhibitor and antiviral agent; structure in first source		2.4520
n-(3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl)-3-(2-((((1,1-dimethylethyl)amino)carbonyl)amino)-3,3-dimethyl-1-oxobutyl)-6,6-dimethyl-3-azabicyclo(3.1.0)hexan-2-carboxamide
boceprevir : A synthetic tripeptide consisting of N-(tert-butylcarbamoyl)-3-methyl-L-valyl, a cyclopropyl-fused prolyl and 3-amino-4-cyclobutyl-2-oxobutanamide residues joined in sequence. Used for treatment of chronic hepatitis C virus genotype 1 infection.		2.0410tripeptide;
ureas		antiviral drug;
hepatitis C protease inhibitor;
peptidomimetic
alisporivir
alisporivir: nonimmunosuppressive cyclosporin analog; structure/sequence in first source		2.4520homodetic cyclic peptideanticoronaviral agent
hcv 796
HCV 796: inhibits HCV RdRp; structure in first source		3.8430
balapiravir
balapiravir: a prodrug of R1479; structure in first source		11.682
nitd008
NITD008: inhibits enterovirus 71		2.1510
sofosbuvir
[no description available]		2.0510
sofosbuvir
Sofosbuvir: A uridine monophosphate analog inhibitor of HEPATITIS C VIRUS (HCV) polymerase NS5B that is used as an ANTIVIRAL AGENT in the treatment of CHRONIC HEPATITIS C.. sofosbuvir : A nucleotide conjugate that is used in combination with ledipasvir (under the trade name Harvoni) for the treatment of chronic hepatitis C genotype 1 infection.		2.5720isopropyl ester;
L-alanyl ester;
nucleotide conjugate;
organofluorine compound;
phosphoramidate ester		antiviral drug;
hepatitis C protease inhibitor;
prodrug
bms-986094
BMS-986094: a prodrug of 2'-C-methylguanosine and antiviral agent		2.1510
als-8176
4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine: an antiviral with RSV polymerase inhibitory activity; structure in first source		2.1110
guanosine monophosphate
Guanosine Monophosphate: A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature.. guanosine 5'-monophosphate : A purine ribonucleoside 5'-monophosphate having guanine as the nucleobase.		2.1510guanosine 5'-phosphate;
purine ribonucleoside 5'-monophosphate		biomarker;
Escherichia coli metabolite;
metabolite;
mouse metabolite
2'-o-methylguanosine
2'-O-methylguanosine : Guanosine with the hydrogen on the hydroxyl at position C-2' substituted with a methyl group.		3.1710methylguanosinemetabolite
3-deoxyguanosine
3'-deoxyguanosine : A 3'-deoxyribonucleoside having guanine as the nucleobase.		3.17103'-deoxyribonucleoside;
guanosines		EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
HIV
Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.		01.9810
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted
[description not available]		03.8840
Hepatitis C
INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.		03.8840
Infections, Respiratory Syncytial Virus
[description not available]		02.1110
Respiratory Syncytial Virus Infections
Pneumovirus infections caused by the RESPIRATORY SYNCYTIAL VIRUSES. Humans and cattle are most affected but infections in goats and sheep have been reported.		02.1110
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.610
HIV Coinfection
[description not available]		02.610
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		02.610
Break-Bone Fever
[description not available]		02.110
Dengue
An acute febrile disease transmitted by the bite of AEDES mosquitoes infected with DENGUE VIRUS. It is self-limiting and characterized by fever, myalgia, headache, and rash. SEVERE DENGUE is a more virulent form of dengue.		02.110
Chronic Hepatitis C
[description not available]		05.0331
Hepatitis C, Chronic
INFLAMMATION of the LIVER in humans that is caused by HEPATITIS C VIRUS lasting six months or more. Chronic hepatitis C can lead to LIVER CIRRHOSIS.		05.0331
Neutropenia
A decrease in the number of NEUTROPHILS found in the blood.		03.4311
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