Page last updated: 2024-11-06

fialuridine

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

Fialuridine, also known as FIAC, is a synthetic nucleoside analog that was initially developed as an antiviral agent for the treatment of hepatitis B virus (HBV) infection. It was designed to inhibit the replication of HBV by acting as a chain terminator during DNA synthesis. However, clinical trials revealed that fialuridine caused severe and potentially fatal hepatotoxicity, leading to its withdrawal from clinical use.'

Cross-References

ID SourceID
PubMed CID50313
CHEMBL ID271475
SCHEMBL ID3189
MeSH IDM0127888

Synonyms (52)

Synonym
nsc-678514
fialuridine (usan/inn)
D04181
1-(2'-deoxy-2'-fluoro-.beta.-d-arabinofuranosyl)-5-iodouracil
fiau
2'-fluoro-5-iodouracil
69123-98-4
fialuridine
1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-iodo-pyrimidine-2,4-dione
1-(2-deoxy-2-fluoro-.beta.-d-arabinofuranosyl)-5-iodouracil
fialuridine [usan:inn]
2'-fluoro-5-iodo-1-beta-d-arabinofuranosyluracil
uracil, 1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-iodo-
c9h10fin2o5
drg-0098
1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-iodouracil
2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-iodo-
fluoroiodoarauridine
CHEMBL271475
1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-iodo-2,4(1h,3h)-pyrimidinedione
1-(2'fluoro-2'-deoxyarabinofuranosyl)-5-iodouracil
1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione
1-(2-deoxy-2-fluoro-b-d-arabinofuranosyl)-5-iodouracil
unii-53t7in77lc
nsc 678514
53t7in77lc ,
AKOS016009483
bdbm50367488
AKOS015856198
1-((2s,3r,4s,5s)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1h,3h)-dione
SCHEMBL3189
2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-2-fluoro-.beta.-d-arabinofuranosyl)-5-iodo-
fialuridine [mi]
fialuridine [mart.]
fialuridine [usan]
fialuridine [inn]
J-700174
J-700352
1-((2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1h,3h)-dione
AC-32361
mfcd00866922
1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
AS-69583
fialuridine, >=98% (hplc)
Q5446286
F12931
DB15427
5-iodo-2-fluoroarauracil
A848801
DTXSID701028030
CS-0065233
HY-118122

Research Excerpts

Overview

Fialuridine (FIAU) is a nucleoside analog that is a substrate for bacterial thymidine kinase (TK) It is an antiviral agent with potent activity against hepatitis B virus replication.

ExcerptReferenceRelevance
"Fialuridine (FIAU) is a nucleoside analog that is a substrate for bacterial thymidine kinase (TK). "( [(124)I]FIAU: Human dosimetry and infection imaging in patients with suspected prosthetic joint infection.
Alavi, A; Barnett, TM; Berkowitz, RD; Bettegowda, C; Cho, SY; Conklin, JJ; Gelb, J; McLeroth, P; Mont, MA; Petit, C; Pomper, MG; Saha, S; Siegel, BA; Spaltro, J; Stabin, MG; Zhang, HH; Zhang, XM, 2016
)
1.88
"Fialuridine (FIAU) is a nucleoside analog with potent activity against hepatitis B virus in vitro and in vivo. "( Effect of fialuridine on replication of mitochondrial DNA in CEM cells and in human hepatoblastoma cells in culture.
Colacino, JM; Jaskunas, SR; Malcolm, SK, 1994
)
2.13
"Fialuridine (FIAU) is a halogen-substituted analog of thymidine that was undergoing clinical investigation as a drug for the treatment of chronic hepatitis B viral infection. "( Sensitive and specific radioimmunoassay for fialuridine: initial assessment of pharmacokinetics after single oral doses to healthy volunteers.
Bowsher, RR; Compton, JA; DeSante, KA; Hatcher, BL; Hyslop, DL; Jones, CD; Kirkwood, JA; Mabry, TE; Place, GD, 1994
)
1.99
"Fialuridine (FIAU) is a thymidine nucleoside analog with activity against various herpesviruses and hepatitis B virus (HBV) in vitro and in vivo. "( Mechanisms for the anti-hepatitis B virus activity and mitochondrial toxicity of fialuridine (FIAU).
Colacino, JM, 1996
)
1.96
"Fialuridine (FIAU) is a thymidine analog effective against hepatitis B virus. "( Fialuridine is phosphorylated and inhibits DNA synthesis in isolated rat hepatic mitochondria.
Colacino, JM; Horn, DM; Neeb, LA; Richardson, FC, 1997
)
3.18
"Fialuridine is an antiviral agent with potent activity against hepatitis B virus replication in vitro and in vivo. "( Mitochondrial injury. Lessons from the fialuridine trial.
de Man, RA; Honkoop, P; Schalm, SW; Scholte, HR, 1997
)
2.01

Actions

ExcerptReferenceRelevance
"fialuridine; FIAU) produce clinically significant mitochondrial toxicity that limits their dose or prevents their use in the clinic."( Mitochondrial expression of the human equilibrative nucleoside transporter 1 (hENT1) results in enhanced mitochondrial toxicity of antiviral drugs.
Lai, Y; Tse, CM; Unadkat, JD, 2004
)
1.04

Toxicity

ExcerptReferenceRelevance
" Although these toxic effects are manifest in many tissues, a common disease mechanism can explain the diverse clinical events."( Mitochondrial toxicity of antiviral drugs.
Dalakas, MC; Lewis, W, 1995
)
0.29
"The development of efficacious and safe new human pharmaceuticals continues to be highly dependent on well-designed and carefully executed animal toxicology studies."( Importance of species selection in drug toxicity testing.
Morton, DM, 1998
)
0.3
" An understanding of structure-activity relationships (SARs) of chemicals can make a significant contribution to the identification of potential toxic effects early in the drug development process and aid in avoiding such problems."( Developing structure-activity relationships for the prediction of hepatotoxicity.
Fisk, L; Greene, N; Naven, RT; Note, RR; Patel, ML; Pelletier, DJ, 2010
)
0.36
" Toxic effects were observed around 10 μM, which is within a range of 10-15 X approximate Cmax."( The utility of a differentiated preclinical liver model, HepaRG cells, in investigating delayed toxicity via inhibition of mitochondrial-replication induced by fialuridine.
Beckett, AJ; Chadwick, AE; Douglas, O; Jenkins, RE; Jolly, CE; Kamalian, L; Monshouwer, M; Park, BK; Penman, SL; Simic, D; Snoeys, J; Williams, DP, 2020
)
0.75

Compound-Compound Interactions

ExcerptReferenceRelevance
" These mt-QSARs offer also a good opportunity to construct drug-drug Complex Networks (CNs) that can be used to explore large and complex drug-viral species databases."( Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.
Chou, KC; González-Díaz, H; Martinez de la Vega, O; Prado-Prado, FJ; Ubeira, FM; Uriarte, E, 2009
)
0.35

Bioavailability

ExcerptReferenceRelevance
" This selection is usually based on pilot toxicity and general pharmacology studies in rodent and non-rodent animals, together with supporting comparative drug disposition studies to determine bioavailability and metabolic profile."( Importance of species selection in drug toxicity testing.
Morton, DM, 1998
)
0.3

Dosage Studied

ExcerptRelevanceReference
" In a comparative study with this 3-day dosage schedule, the efficacy of daily doses of 50 mg of FMAU per kg was greater than that of the same doses of FIAC and FIAU, in that order; all these were more effective than daily doses of 50, 100, or 200 mg of acyclovir or of 500 mg of phosphonoformic acid per kg."( Treatment of primary acute genital herpes in guinea pigs by intraperitoneal administration of fluoropyrimidines.
Hsiung, GD; Mayo, DR, 1984
)
0.27
" We proposed a systematic classification scheme using FDA-approved drug labeling to assess the DILI potential of drugs, which yielded a benchmark dataset with 287 drugs representing a wide range of therapeutic categories and daily dosage amounts."( FDA-approved drug labeling for the study of drug-induced liver injury.
Chen, M; Fang, H; Liu, Z; Shi, Q; Tong, W; Vijay, V, 2011
)
0.37
"To assess biodistribution and dosimetry, six subjects with suspected hip or knee PJI and six healthy subjects underwent serial PET/CT after being dosed with 74MBq (2mCi) [(124)I]FIAU intravenously (IV)."( [(124)I]FIAU: Human dosimetry and infection imaging in patients with suspected prosthetic joint infection.
Alavi, A; Barnett, TM; Berkowitz, RD; Bettegowda, C; Cho, SY; Conklin, JJ; Gelb, J; McLeroth, P; Mont, MA; Petit, C; Pomper, MG; Saha, S; Siegel, BA; Spaltro, J; Stabin, MG; Zhang, HH; Zhang, XM, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpRattus norvegicus (Norway rat)IC50 (µMol)1,000.00000.40002.75008.6000AID1209456
Bile salt export pumpHomo sapiens (human)IC50 (µMol)1,000.00000.11007.190310.0000AID1209455
Thymidine kinase, cytosolicHomo sapiens (human)Ki0.54500.09001.52137.0000AID210534; AID210537
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine kinase, cytosolicHomo sapiens (human)Km53.00000.29002.27675.0000AID210540
Thymidine kinaseVaccinia virus WRKm4.30004.30004.30004.3000AID324741
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (28)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
nucleobase-containing compound metabolic processThymidine kinase, cytosolicHomo sapiens (human)
deoxyribonucleoside monophosphate biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine metabolic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
protein homotetramerizationThymidine kinase, cytosolicHomo sapiens (human)
DNA synthesis involved in mitotic DNA replicationThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
thymidine kinase activityThymidine kinase, cytosolicHomo sapiens (human)
protein bindingThymidine kinase, cytosolicHomo sapiens (human)
ATP bindingThymidine kinase, cytosolicHomo sapiens (human)
zinc ion bindingThymidine kinase, cytosolicHomo sapiens (human)
identical protein bindingThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
nucleusThymidine kinase, cytosolicHomo sapiens (human)
cytosolThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (85)

Assay IDTitleYearJournalArticle
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1209457Unbound Cmax in human plasma2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID217755Compound was evaluated for antiviral activity against Herpes simplex virus (HSV) -2 (MS) in Vero cell cultures1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID217888Antiviral activity against HSV-1 (Brand) in Vero cells1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID86032Effective concentration required to inhibit replication of strain F of HSV-1 by 50%1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Nucleosides. 139. Synthesis and anticytomegalovirus and antiherpes simplex virus activity of 5'-modified analogues of 2'-fluoroarabinosylpyrimidine nucleosides.
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.
AID324741Activity of Vaccinia virus WR thymidine kinase assessed as ATP utilization by luciferase-based assay2007Antimicrobial agents and chemotherapy, May, Volume: 51, Issue:5
Selective phosphorylation of antiviral drugs by vaccinia virus thymidine kinase.
AID217420Proliferation of Vero cells by propagation on day 4 by measuring optical density (absorbance) at 30 ug/mL1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID217754Compound was evaluated for antiviral activity against Herpes simplex virus (HSV) -1 (BW) in Vero cell cultures1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID83146Antiviral activity against VZV (Ellen) in human lung fibroblast (HLF-1) cells1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1474167Liver toxicity in human assessed as induction of drug-induced liver injury by measuring verified drug-induced liver injury concern status2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID324744Ratio of Vmax to Km for human thymidine kinase 12007Antimicrobial agents and chemotherapy, May, Volume: 51, Issue:5
Selective phosphorylation of antiviral drugs by vaccinia virus thymidine kinase.
AID86209Proliferation of Hep-2 cells by propagation on day 4 by measuring optical density (absorbance) at 330 ug/mL1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID86216Antiviral activity against HSV-2 (K979) in human epithelial (Hep-2) cells1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID391675Cytotoxicity against RG2 cells after 72 hrs by MTT assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Synthesis and in vitro evaluation of 5-[(18)f]fluoroalkyl pyrimidine nucleosides for molecular imaging of herpes simplex virus type 1 thymidine kinase reporter gene expression.
AID218068Compound was evaluated for cellular toxicity performed on Vero cells measured as 50% tissue culture inhibitory dose after 72 hr post exposure1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID324743Activity of human thymidine kinase 1 assessed as ATP utilization by luciferase-based assay2007Antimicrobial agents and chemotherapy, May, Volume: 51, Issue:5
Selective phosphorylation of antiviral drugs by vaccinia virus thymidine kinase.
AID216191Compound was evaluated for cytotoxicity in rapidly dividing Vero cells1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Nucleosides. 139. Synthesis and anticytomegalovirus and antiherpes simplex virus activity of 5'-modified analogues of 2'-fluoroarabinosylpyrimidine nucleosides.
AID116575Compound was evaluated for its effect on HSV -2 induced mortality in mice measured as mean survival time (MST) at the dose of 12.5 mg/kg per day1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
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.
AID74002Compound (5%) was evaluated for its effect on (no. of areas =3) time to start healing in HSV-1 cutaneous infection of guinea pig; expressed as time to start healing1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
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.
AID86034Effective concentration required to inhibit replication of strain F of HSV-1 by 90%1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Nucleosides. 139. Synthesis and anticytomegalovirus and antiherpes simplex virus activity of 5'-modified analogues of 2'-fluoroarabinosylpyrimidine nucleosides.
AID84941Effective concentration required to inhibit replication of strain G of HSV-2 by 50%1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Nucleosides. 139. Synthesis and anticytomegalovirus and antiherpes simplex virus activity of 5'-modified analogues of 2'-fluoroarabinosylpyrimidine nucleosides.
AID1209456Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID107298Compound was evaluated for its effect of HSV -2 induced mortality in mice measured as survivors/total (%) at the dose of 25 mg/kg per day; 5/101987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID73997Compound (5%) was evaluated for its effect on (no. of areas = 3)maximum score in HSV-1 cutaneous infection of guinea pig; expressed as maximum score1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
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.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID107293Compound was evaluated for its effect of HSV -2 induced mortality in mice measured as survivors/total (%) at the dose of 100 mg/kg per day; 3/101987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID107296Compound was evaluated for its effect of HSV -2 induced mortality in mice measured as survivors/total (%) at the dose of 200 mg/kg per day; 6/101987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID107295Compound was evaluated for its effect of HSV -2 induced mortality in mice measured as survivors/total (%) at the dose of 12.5 mg/kg per day; 2/101987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID625293Drug Induced Liver Injury Prediction System (DILIps) validation dataset; compound DILI positive/negative as observed in LTKB-BD2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625276FDA Liver Toxicity Knowledge Base Benchmark Dataset (LTKB-BD) drugs of most concern for DILI2011Drug discovery today, Aug, Volume: 16, Issue:15-16
FDA-approved drug labeling for the study of drug-induced liver injury.
AID1474166Liver toxicity in human assessed as induction of drug-induced liver injury by measuring severity class index2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID156700Antiviral activity against HSV-1 (KOS) in Primary Rabbit Kidney (PRK) cells1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID588210Human drug-induced liver injury (DILI) modelling dataset from Ekins et al2010Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 38, Issue:12
A predictive ligand-based Bayesian model for human drug-induced liver injury.
AID218067Compound was evaluated for cellular toxicity performed on Vero cells measured as 50% tissue culture inhibitory dose after 120 hr post exposure1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID156701Antiviral activity against HSV-2 (G) in Primary Rabbit Kidney (PRK) cells1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID116576Compound was evaluated for its effect on HSV -2 induced mortality in mice measured as mean survival time (MST) at the dose of 200 mg/kg per day1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID116574Compound was evaluated for its effect on HSV -2 induced mortality in mice measured as mean survival time (MST) at the dose of 100 mg/kg per day1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID86207Proliferation of Hep-2 cells by propagation on day 4 by measuring optical density (absorbance) at 100 ug/mL1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID210540Compound was evaluated for Kinetic constant for cellular thymidine kinase in Vero cells1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID116577Compound was evaluated for its effect on HSV -2 induced mortality in mice measured as mean survival time (MST) at the dose of 25 mg/kg per day1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
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.
AID391428Inhibition of [125I]FIAU uptake in RG2TK+ cells overexpressing HSV1-tk gene2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Synthesis and in vitro evaluation of 5-[(18)f]fluoroalkyl pyrimidine nucleosides for molecular imaging of herpes simplex virus type 1 thymidine kinase reporter gene expression.
AID217889Antiviral activity against HSV-2 (K979) in Vero cells1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID107300Compound was evaluated for its effect of HSV -2 induced mortality in mice measured as survivors/total (%) at the dose of 50 mg/kg per day; 5/101987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID73995Compound (5%) was evaluated for its effect on (no. of areas = 3) mean area under lesion score-day curve in HSV-1 cutaneous infection of guinea pig; expressed as mean area under lesion score-day curve1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID217421Proliferation of Vero cells by propagation on day 4 by measuring optical density (absorbance) at 330 ug/mL1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID1209455Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans.
AID84943Effective concentration required to inhibit replication of strain G of HSV-2 by 90%1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Nucleosides. 139. Synthesis and anticytomegalovirus and antiherpes simplex virus activity of 5'-modified analogues of 2'-fluoroarabinosylpyrimidine nucleosides.
AID210534Compound was evaluated for Kinetic constant for viral thymidine kinase of Herpes simplex virus (HSV) -11987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID74001Compound (5%) was evaluated for its effect on (no. of areas = 4)mean peak lesion score in HSV-1 cutaneous infection of guinea pig; expressed as mean peak lesion score1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID392504Antiviral activity against Cowpox virus2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID116578Compound was evaluated for its effect on HSV -2 induced mortality in mice measured as mean survival time (MST) at the dose of 50 mg/kg per day1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID588209Literature-mined public compounds from Greene et al multi-species hepatotoxicity modelling dataset2010Chemical research in toxicology, Jul-19, Volume: 23, Issue:7
Developing structure-activity relationships for the prediction of hepatotoxicity.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID86208Proliferation of Hep-2 cells by propagation on day 4 by measuring optical density (absorbance) at 30 ug/mL1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
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.
AID324742Ratio of Vmax to Km for Vaccinia virus WR thymidine kinase2007Antimicrobial agents and chemotherapy, May, Volume: 51, Issue:5
Selective phosphorylation of antiviral drugs by vaccinia virus thymidine kinase.
AID86215Antiviral activity against HSV-1 (Brand) in human epithelial (Hep-2) cells1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID391674Cytotoxicity against HSV1-tk gene overexpressing RG2TK+ cells after 72 hrs by MTT assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Synthesis and in vitro evaluation of 5-[(18)f]fluoroalkyl pyrimidine nucleosides for molecular imaging of herpes simplex virus type 1 thymidine kinase reporter gene expression.
AID625294Drug Induced Liver Injury Prediction System (DILIps) validation dataset; compound DILI positive/negative as observed in O'Brien data2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1204710Inhibition of human mitochondrial DNA polymerase gamma large subunit/DNA polymerase gamma accessory subunit using 32P-D19/D36 as DNA primer/template assessed as single nucleotide incorporation rate at 100 uM after 5 to 90 mins by PAGE analysis relative to2015Bioorganic & medicinal chemistry letters, Jun-15, Volume: 25, Issue:12
Discovery of β-D-2'-deoxy-2'-α-fluoro-4'-α-cyano-5-aza-7,9-dideaza adenosine as a potent nucleoside inhibitor of respiratory syncytial virus with excellent selectivity over mitochondrial RNA and DNA polymerases.
AID217419Proliferation of Vero cells by propagation on day 4 by measuring optical density (absorbance) at 100 ug/mL1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.
AID210537Compound was evaluated for Kinetic constant for viral thymidine kinase of Herpes simplex virus (HSV) -21987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID625295Drug Induced Liver Injury Prediction System (DILIps) validation dataset; compound DILI positive/negative as observed in Pfizer data2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (153)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (11.11)18.7374
1990's61 (39.87)18.2507
2000's48 (31.37)29.6817
2010's25 (16.34)24.3611
2020's2 (1.31)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.85

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 Index31.85 (24.57)
Research Supply Index5.09 (2.92)
Research Growth Index4.77 (4.65)
Search Engine Demand Index40.78 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.85)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (3.18%)5.53%
Reviews9 (5.73%)6.00%
Case Studies1 (0.64%)4.05%
Observational0 (0.00%)0.25%
Other142 (90.45%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (4)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Biodistribution and Dosimetry of [124i]FIAU in Patients With Prosthetic Joint Infection of The Knee or Hip and Healthy Subjects Using PET-CT Scanning [NCT01337466]Phase 112 participants (Actual)Interventional2010-12-31Completed
Study of Imaging of Viral Thymidine Kinase Activity in EBV-Associated and KSHV-Associated Malignancies [NCT00982449]12 participants (Actual)Interventional2010-12-31Completed
The Tolerance of HIV-Infected Patients With Herpes Group Virus Infections to Oral Doses of FIAU [NCT00000654]Phase 278 participants InterventionalCompleted
Sensitivity and Specificity of [124I]FIAU PET-CT Scanning in Patients Presenting With Pain in a Prosthetic Knee or Hip Joint [NCT01705496]Phase 223 participants (Actual)Interventional2012-08-31Terminated(stopped due to The sensitivity and specificity were not able to be assessed in this study due to the poor image quality.)
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT01705496 (2) [back to overview]Estimate the Sensitivity and Specificity of [124I]FIAU
NCT01705496 (2) [back to overview]Evaluate the Safety and Tolerability of [124I]FIAU

Estimate the Sensitivity and Specificity of [124I]FIAU

"The sensitivity and specificity of [124I]FIAU in the detection of prosthetic joint infection was determined based on the correlation of the patient's infection status determined by an independent image reviewer and the infection status assessed by an adjudication committee.~Presence or absence of infection: Images were to be assessed and optimized on an ongoing basis. The single blinded reader was to assess independently the PET-CT images (attenuation corrected [AC] and non-AC PET plus the AC CT) and provide a diagnosis (infected or uninfected) using the chosen parameter(s) without knowing the results of the surgery. The radiology reviewer was not given any additional clinical information on the patient for reassessments relative to the initial reads. A separate central radiologist was to read the comparator X-rays independently for the presence or absence of infection. All pathology slides were to be read by a single pathologist. Local microbiology results were to be used." (NCT01705496)
Timeframe: 30 hours

Interventionpercentage of participants (Number)
[124I]FIAU80

[back to top]

Evaluate the Safety and Tolerability of [124I]FIAU

Safety will be monitored throughout the study for all subjects. safety will be assessed by monitoring of adverse events,vital signs,physical exams, and clinical laboratory tests including CBC, serum chemistry. (NCT01705496)
Timeframe: 30 +/- 2 days

Interventionparticipants with adverse events (Number)
[124I]FIAU15

[back to top]