Page last updated: 2024-12-06

ibacitabine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Ibacitabine, a nucleoside analogue of cytidine, is a potent inhibitor of DNA polymerase and has shown significant antiviral activity against hepatitis B virus (HBV). Its synthesis involves the modification of cytidine with a 5-iodo substituent. Ibacitabine is studied due to its potential as an antiviral agent, particularly against HBV, which can lead to chronic liver disease and liver cancer. Its mechanism of action involves incorporation into viral DNA, ultimately halting viral replication. Its effectiveness and safety in the treatment of chronic HBV infection are under active investigation.'

ibacitabine: antiherpetic agent [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65050
CHEMBL ID158653
CHEMBL ID2104340
CHEBI ID135996
SCHEMBL ID225402
MeSH IDM0057479

Synonyms (50)

Synonym
nsc-527083
ibacitabine (inn)
D07200
4-amino-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-iodo-pyrimidin-2-one
5-iodo-2'-deoxycytidine
IDC ,
611-53-0
nsc 527083
ibacitabina [spanish]
2'-deoxy-5-iodocytidine
ibacitabine [inn]
ibacitabinum [latin]
ccris 2826
ibacitabine
ai3-62629
c9h12in3o4
einecs 210-269-8
CHEBI:135996
chembl158653
4-amino-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-iodo-1h-pyrimidin-2-one
bdbm50028585
4-amino-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one; 5-idc;4-amino-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidin-2(1h)-one
A833066
4-amino-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidin-2(1h)-one
AKOS015917916
CHEMBL2104340
unii-3ek8532dzv
ibacitabina
3ek8532dzv ,
ibacitabinum
AKOS015853900
HG1100
ibacitabine [who-dd]
ibacitabine [mart.]
SCHEMBL225402
J-700095
5-iodo-2'deoxycytidine
WEVJJMPVVFNAHZ-RRKCRQDMSA-N
DTXSID50209985
sr-01000945259
SR-01000945259-1
DB13776
DS-14588
CS-W011854
Q5983577
AMY8816
ibacitabin
5-iodo-2 inverted exclamation marka-deoxycytidineai3-62629
HY-W011138
BP-58650
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pyrimidine 2'-deoxyribonucleoside
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine kinase, cytosolic Rattus norvegicus (Norway rat)Ki7,450.00002.40004.20006.5000AID126599; AID210886
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID1124512Inhibition of thymidine kinase in BHK21 (C13) cells using [14C]thymidine at 0.19 mM after 10 mins by liquid scintillation spectrometer analysis relative to control in presence of Mg2+1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Design of species- or isozyme-specific enzyme inhibitors. 1. Effect of thymidine substituents on affinity for the thymidine site of hamster cytoplasmic thymidine kinase.
AID1131486Cytotoxicity against African green monkey Vero cells at 800 uM after 3 days by haemocytometry1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
A novel synthesis and biological activity of several 5-halo-5'-amino analogues of deoxyribopyrimidine nucleosides.
AID1131485Cytotoxicity against African green monkey Vero cells at 50 uM after 3 days by haemocytometry1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
A novel synthesis and biological activity of several 5-halo-5'-amino analogues of deoxyribopyrimidine nucleosides.
AID1123146Cytotoxicity against mouse P815 cells assessed as growth inhibition after 96 hrs1979Journal of medicinal chemistry, Jan, Volume: 22, Issue:1
Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides.
AID1123153Antiviral activity against HSV1 2931 infected in African green monkey Vero cells assessed as inhibition of virus replication at 0.1 ug/ml after 24 hrs relative to control1979Journal of medicinal chemistry, Jan, Volume: 22, Issue:1
Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides.
AID1124513Inhibition of human mitochondrial thymidine kinase using [14C]thymidine at 0.19 mM after 10 mins by liquid scintillation spectrometer analysis relative to control in presence of Mg2+1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Design of species- or isozyme-specific enzyme inhibitors. 1. Effect of thymidine substituents on affinity for the thymidine site of hamster cytoplasmic thymidine kinase.
AID1123152Antiviral activity against HSV1 2931 infected in African green monkey Vero cells assessed as inhibition of virus replication at 0.01 ug/ml after 24 hrs relative to control1979Journal of medicinal chemistry, Jan, Volume: 22, Issue:1
Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides.
AID126599Noncompetitive inhibition against rat mitochondrial thymidine kinase1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Species- or isozyme-specific enzyme inhibitors. 5. Differential effects of thymidine substituents on affinity for rat thymidine kinase isozymes.
AID1123151Cytotoxicity against mouse L5178Y cells assessed as growth inhibition after 96 hrs1979Journal of medicinal chemistry, Jan, Volume: 22, Issue:1
Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides.
AID1131481Antiviral activity against HSV1 CL101 infected in African green monkey Vero cells assessed as plaque forming unit at 50 uM after 40 hrs relative to control1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
A novel synthesis and biological activity of several 5-halo-5'-amino analogues of deoxyribopyrimidine nucleosides.
AID1123148Antiviral activity against HSV1 2931 infected in African green monkey Vero cells assessed as inhibition of virus replication at 1 ug/ml after 24 hrs relative to control1979Journal of medicinal chemistry, Jan, Volume: 22, Issue:1
Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides.
AID1135817Retention time of the compound by liquid chromatography1978Journal of medicinal chemistry, Nov, Volume: 21, Issue:11
Synthesis and biological activities of some uronic acids, uronates, uronamides, and urononitriles of pyrimidine nucleosides.
AID1124514Inhibition of human cytoplasmic thymidine kinase using [14C]thymidine at 0.19 mM after 10 mins by liquid scintillation spectrometer analysis relative to control in presence of Mg2+1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Design of species- or isozyme-specific enzyme inhibitors. 1. Effect of thymidine substituents on affinity for the thymidine site of hamster cytoplasmic thymidine kinase.
AID210886Competitive inhibition against rat cytoplasmic Thymidine kinase1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Species- or isozyme-specific enzyme inhibitors. 5. Differential effects of thymidine substituents on affinity for rat thymidine kinase isozymes.
AID1123149Antiviral activity against HSV1 2931 infected in African green monkey Vero cells assessed as inhibition of virus replication at 10 ug/ml after 24 hrs relative to control1979Journal of medicinal chemistry, Jan, Volume: 22, Issue:1
Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides.
AID1123150Antiviral activity against HSV1 2931 infected in African green monkey Vero cells assessed as inhibition of virus replication at 100 ug/ml after 24 hrs relative to control1979Journal of medicinal chemistry, Jan, Volume: 22, Issue:1
Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (44)

TimeframeStudies, This Drug (%)All Drugs %
pre-199032 (72.73)18.7374
1990's7 (15.91)18.2507
2000's2 (4.55)29.6817
2010's3 (6.82)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: 22.10

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index22.10 (24.57)
Research Supply Index3.91 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.10)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (4.26%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other45 (95.74%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]