Page last updated: 2024-11-04

arabinofuranosyluracil

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

Description

Arabinofuranosyluracil: A pyrimidine nucleoside formed in the body by the deamination of CYTARABINE. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID18323
CHEMBL ID1092065
CHEBI ID68346
SCHEMBL ID359587
MeSH IDM0001641
PubMed CID12219138
SCHEMBL ID360394
MeSH IDM0001641

Synonyms (60)

Synonym
spongouridine
arauridine
uracil arabinoside
uracil 1-beta-d-arabinofuranoside, lymphoma antiproliferative
1beta-d-arabinofuranosyluracil
1-beta-d-arabinofurnosyluracil
uracil, 1-beta-d-arabinofuranosyl-
ara-u
1-beta-d-arabinofuranosyluracil
uridine arabinoside
nsc 68928
brn 0028749
spongouridine (van)
uracil, 1-beta-d-arabinofuranosyl- (van)
einecs 221-386-9
uracil-beta-d-arabinofuranoside
1-beta-d-arabinofuranosyl-(1h,3h)-pyrimidine-2,4-dione
chebi:68346 ,
CHEMBL1092065
unii-zk0wmw5nqf
zk0wmw5nqf ,
5-24-06-00136 (beilstein handbook reference)
1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-oxolanyl]pyrimidine-2,4-dione
1-[(2r,3s,4s,5r)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]pyrimidine-2,4-dione
A820641
AKOS015969693
uracil 1-|a-d-arabinofuranoside
S4807
1-((2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
1-| cent-d-arabinofuranosyluracil
HG1013
DRTQHJPVMGBUCF-CCXZUQQUSA-N
1-(beta-d-arabinofuranosyl)uracil
1-(beta-d-arabinofuranosyl)-pyrimidin-2,4(3h)-dione
uracil-1-beta-d-arabinofuranoside
J-700006
SCHEMBL359587
1-?-d-arabinofuranosyluracil
DTXSID80184832
uracil arabinoside, united states pharmacopeia (usp) reference standard
2,4(1h,3h)-pyrimidinedione, 1-.beta.-d-arabinofuranosyl-
uracil arabinoside, european pharmacopoeia (ep) reference standard
1-beta-d-arabinofuranosylpyrimidine-2,4(1h,3h)-dione (uracil arabinoside)
SW220050-1
Q27136843
DS-14592
uracil 1-b-d-arabinofuranoside
BCP29295
CS-0083204
HY-N6652
CCG-266899
uracil arabinoside [usp-rs]
1-.beta.-d-arabinofuranosyl-2,4(1h,3h)-pyrimidinedione
uracil 1--d-arabinofuranoside
1-eta--rabinofuranosyluracl
uracil 1- beta -d-arabinofuranoside
arabinofuranosyluracil
AKOS015896937
SCHEMBL360394
1-[(3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In the initial phase I trial neurotoxicity, characterized by extrapyramidal dysfunction, was found to be the dose-limiting toxic effect, and a dosage of 32 mg/m2/day for 5 days was suggested for phase II studies."( Phase I trial of 1-(2'-deoxy-2'-fluoro-1-beta-D-arabinofuranosyl)-5-methyluracil (FMAU) terminated by severe neurologic toxicity.
Abbruzzese, JL; Castellanos, AM; Krakoff, IH; Legha, SS; Levy, JK; Raber, MN; Schmidt, S, 1989
)
0.28
" 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
" Clevudine was well tolerated with no severe/serious adverse events."( Clinical trial: a phase II, randomized study evaluating the safety, pharmacokinetics and anti-viral activity of clevudine for 12 weeks in patients with chronic hepatitis B.
Blum, MR; Hann, HW; Lau, GK; Leung, N; Lim, SG; Marcellin, P; Mommeja-Marin, H; Moxham, C; Rousseau, F; Snow, A; Sorbel, J; Trepo, C, 2008
)
0.35
" In general, the most toxic compound was 5-FU."( Ecotoxicity and genotoxicity assessment of cytotoxic antineoplastic drugs and their metabolites.
Blaha, L; Dott, W; Kovalova, L; Zounkova, R, 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
)
0.56

Pharmacokinetics

ExcerptReferenceRelevance
") administration, FEAU was cleared from the plasma primarily unchanged, with a terminal half-life of 58 to 80 min in the mouse and 63 to 78 min in the rat."( Preclinical pharmacology and pharmacokinetics of the anti-hepatitis virus agent 2'-fluoro-5-ethyl-1-beta-D-arabinofuranosyluracil in mice and rats.
Chiang, J; Chou, TC; Gloff, CA; Kong, XB; Tong, WP; Vidal, P, 1992
)
0.28
" This results in a decrease in ara-C catabolism and prolongs the plasma half-life of ara-C."( Modulation of the metabolism and pharmacokinetics of 1-beta-D-arabinofuranosylcytosine by 1-beta-D-arabinofuranosyluracil in leukemic mice.
Capizzi, RL; Chandrasekaran, B; Dimling, J; Kute, TE; Morgan, T, 1989
)
0.28
" During a phase I study in patients with advanced low-grade non-Hodgkin lymphomas or acute myeloid leukemia, the pharmacokinetic parameters of Ara-CMP-Stearate (kindly provided by ASTA Medica, Frankfurt, Germany) were determined by HPLC analysis."( Pharmacokinetics of Ara-CMP-Stearate (YNK01): phase I study of the oral Ara-C derivative.
Braess, J; Hiddemann, W; Kaufmann, C; Ramsauer, B; Schleyer, E; Schüssler, M; Unterhalt, M; Wilde, S, 1995
)
0.29
" Concentrations of 882C87 and its main metabolite, the pyrimidine base 5-(1-propynyl)uracil (5PU), in plasma and urine were assayed by an automated sequential trace enrichment of dialysate-high-performance liquid chromatography procedure, and noncompartmental pharmacokinetic parameters were derived from the data."( Pharmacokinetics and tolerability of single oral doses of 882C87, a potent, new anti-varicella-zoster virus agent, in healthy volunteers.
Crome, P; Holdich, TA; Peck, RW; Posner, J; Weatherley, BC; Wootton, R, 1995
)
0.29
" Pharmacokinetic parameters were generated by using area-moment analysis."( Pharmacokinetics of 1-(2-deoxy-2-fluoro-beta-L-arabinofuranosyl)-5-methyluracil (L-FMAU) in rats.
Boudinot, FD; Chu, CK; Ma, T; Wright, JD, 1995
)
0.29
" The elimination half-life of netivudine was approximately 15 h in subjects with normal renal function and 60 h in RF patients."( Pharmacokinetics of netivudine, a potent anti-varicella zoster virus drug, in patients with renal impairment.
Bidault, R; Chretien, P; Fillastre, JP; Gillotin, C; Godin, M; Legallicier, B; Peck, RW; Posner, J; Wooton, R, 1996
)
0.29
" The objective of this study was to characterize the bioavailability and pattern of L-FMAU absorption using a pharmacokinetic model which incorporated two separate absorption processes following oral administration of the nucleoside in an animal model, the rat."( Discontinuous oral absorption pharmacokinetic model and bioavailability of 1-(2-fluoro-5-methyl-beta-L-arabinofuranosyl)uracil (L-FMAU) in rats.
Boudinot, FD; Chu, CK; Ma, T; Wright, JD, 1996
)
0.29
"Cytarabine is intracellularly activated and correlations have been established between the pharmacokinetic behaviour of active metabolites and their antileukemic effect."( Pharmacokinetics of high-dose cytarabine and its deamination product--a reappraisal.
Arning, M; Burk, M; Fartash, K; Heyll, A; Schneider, W; Volmer, M, 1997
)
0.3
" We performed pharmacokinetic measurements with [(14)C]FMAU and PET studies with [(11)C]FMAU using rats bearing several different syngeneic tumors."( Pharmacokinetics of the thymidine analog 2'-fluoro-5-methyl-1-beta-D-arabinofuranosyluracil (FMAU) in tumor-bearing rats.
Alauddin, MM; Bading, JR; Bathija, P; Conti, PS; Fissekis, JD; Koda, RT; Koszalka, GW; Shahinian, AH; Vail, A, 2004
)
0.32
"To characterize pharmacokinetic and pharmacodynamic profile of clevudine, a potent hepatitis B polymerase inhibitor."( Clinical trial: a phase II, randomized study evaluating the safety, pharmacokinetics and anti-viral activity of clevudine for 12 weeks in patients with chronic hepatitis B.
Blum, MR; Hann, HW; Lau, GK; Leung, N; Lim, SG; Marcellin, P; Mommeja-Marin, H; Moxham, C; Rousseau, F; Snow, A; Sorbel, J; Trepo, C, 2008
)
0.35
" The mean plasma half-life of clevudine was 70 h and consequently is not the cause of the delayed viral rebound seen in some patients."( Clinical trial: a phase II, randomized study evaluating the safety, pharmacokinetics and anti-viral activity of clevudine for 12 weeks in patients with chronic hepatitis B.
Blum, MR; Hann, HW; Lau, GK; Leung, N; Lim, SG; Marcellin, P; Mommeja-Marin, H; Moxham, C; Rousseau, F; Snow, A; Sorbel, J; Trepo, C, 2008
)
0.35
" Ara-C and its metabolite Ara-U in plasma and dialyzate were measured chromatographically, and the data subjected to pharmacokinetic analysis."( Effective clearance of Ara-U the major metabolite of cytosine arabinoside (Ara-C) by hemodialysis in a patient with lymphoma and end-stage renal failure.
Cain, M; Cull, GM; Hackett, LP; Ilett, KF; Radeski, D, 2011
)
0.37
" This study presents a model-based approach to integrating dynamic positron emission tomography (PET) and conventional plasma pharmacokinetic studies to characterize the plasma and tissue pharmacokinetics of FAU and FMAU."( Integrating Dynamic Positron Emission Tomography and Conventional Pharmacokinetic Studies to Delineate Plasma and Tumor Pharmacokinetics of FAU, a Prodrug Bioactivated by Thymidylate Synthase.
Douglas, KA; Kim, S; Lawhorn-Crews, JM; Li, J; LoRusso, PM; Mangner, TJ; McHugh, CI; Shields, AF; Wu, J, 2016
)
0.43
" The quantitative determination of Ara-C in plasma is challenging due the required sensitivity because of the short half-life of this drug (i."( Simultaneous determination of cytosine arabinoside and its metabolite uracil arabinoside in human plasma by LC-MS/MS: Application to pharmacokinetics-pharmacogenetics pilot study in AML patients.
Berda-Haddad, Y; Ciccolini, J; Costello, R; Donnette, M; Fanciullino, R; Farnault, L; Giocanti, M; Hau, LTT; Lacarelle, B; Ouafik, L; Solas, C; Venton, G, 2019
)
0.51

Compound-Compound Interactions

ExcerptReferenceRelevance
"2 mg/kg/day when administered in combination with a sub-effective dose of human recombinant interferon-beta."( Inhibition of simian varicella virus infection of monkeys by 1-(2-deoxy-2- fluoro-1-beta-D-arabinofuranosyl)-5-ethyluracil (FEAU) and synergistic effects of combination with human recombinant interferon-beta.
Chou, TC; Fox, JJ; Gloff, CA; Soike, KF; Watanabe, KA, 1990
)
0.28
"We have evaluated the effect of nucleoside related compounds on a murine tumor given with local radiotherapy and on the survival rate following whole body irradiation."( [The modification of radiation effect by nucleoside related compounds on a murine tumor given with local radiotherapy and on survival following whole body irradiation].
Sougawa, M; Tanaka, Y, 1989
)
0.28
" Worldwide recognition of this potentially fatal drug-drug interaction led to subsequent disapproval in the US and elsewhere."( Sorivudine and 5-fluorouracil; a clinically significant drug-drug interaction due to inhibition of dihydropyrimidine dehydrogenase.
Diasio, RB, 1998
)
0.3
" These are applied for query development for identification of possible drug-drug interaction."( Drug interaction ontology (DIO) for inferences of possible drug-drug interactions.
Konagaya, A; Satou, K; Yoshikawa, S, 2004
)
0.32
" We investigated the activity of clevudine (CLV) in combination with other nucleoside/nucleotide analogues to determine if these combinations were compatible in vitro."( Evaluation of the in vitro anti-HBV activity of clevudine in combination with other nucleoside/nucleotide inhibitors.
Bao, H; Furman, PA; Korba, B; Micolochick Steuer, HM; Murakami, E; Niu, C; Tolstykh, T, 2010
)
0.36
"Using the HepAD38 cell line, which expresses wild-type HBV, and a real-time PCR assay, we tested the anti-HBV activity of CLV in combination with entecavir, lamivudine, adefovir, tenofovir and telbivudine (TBV)."( Evaluation of the in vitro anti-HBV activity of clevudine in combination with other nucleoside/nucleotide inhibitors.
Bao, H; Furman, PA; Korba, B; Micolochick Steuer, HM; Murakami, E; Niu, C; Tolstykh, T, 2010
)
0.36
"When CLV was combined with entecavir, lamivudine, adefovir or tenofovir, a synergistic antiviral effect was observed; however, the combination of CLV and TBV gave an antagonistic antiviral response."( Evaluation of the in vitro anti-HBV activity of clevudine in combination with other nucleoside/nucleotide inhibitors.
Bao, H; Furman, PA; Korba, B; Micolochick Steuer, HM; Murakami, E; Niu, C; Tolstykh, T, 2010
)
0.36

Bioavailability

ExcerptReferenceRelevance
"Rectal bioavailability of Ara-C (serum AUC 4 h: 65 micrograms h-1 ml-1) administered in a suppository formulation containing tetrahydrouridine (a deamination inhibitor) and sodium salicylate (an adjuvant) to dogs was better than that from a suppository formulation without tetrahydrouridine (serum AUC 4 h: 18 micrograms h-1 ml-1)."( Enhanced serum concentrations of Ara-C using suppositories containing tetrahydrouridine as a deamination inhibitor of Ara-C.
Engle, KK; Higuchi, T; Liversidge, GG; Nishihata, T, 1986
)
0.27
" The bioavailability and disposition of 882C87, an anti-varicella zoster virus (VZV) agent, have been investigated in healthy young and elderly volunteers."( The bioavailability and disposition of 1-(beta-D-arabinofuranosyl)-5-(1-propynyl)uracil (882C87), a potent, new anti-varicella zoster virus agent.
Jackson, SH; Lee, DR; Peck, RW; Posner, J; Wootton, R, 1995
)
0.29
" The first approach was directed towards improving the bioavailability of acyclovir by examining the potential of a variety of prodrugs, leading to the new compound valaciclovir hydrochloride."( Review of research leading to new anti-herpesvirus agents in clinical development: valaciclovir hydrochloride (256U, the L-valyl ester of acyclovir) and 882C, a specific agent for varicella zoster virus.
Beauchamp, LM; Darby, G; de Miranda, P; Ertl, P; Krenitsky, TA; Lacey, S; Powell, KL; Purifoy, DJ; Rahim, SG; Roberts, G, 1993
)
0.29
" One might question, as these data unfold, the relative value of drugs with such enhanced in vitro activity and oral bioavailability as compared with standard therapeutic agents."( Sorivudine: a promising drug for the treatment of varicella-zoster virus infection.
Whitley, RJ, 1995
)
0.29
" One might question, as these data unfold, the relative clinical value of antivirals with such enhanced in vitro activity and oral bioavailability as compared to standard compounds."( Sorivudine: a potent inhibitor of varicella zoster virus replication.
Whitley, RJ, 1996
)
0.29
" The objective of this study was to characterize the bioavailability and pattern of L-FMAU absorption using a pharmacokinetic model which incorporated two separate absorption processes following oral administration of the nucleoside in an animal model, the rat."( Discontinuous oral absorption pharmacokinetic model and bioavailability of 1-(2-fluoro-5-methyl-beta-L-arabinofuranosyl)uracil (L-FMAU) in rats.
Boudinot, FD; Chu, CK; Ma, T; Wright, JD, 1996
)
0.29
" Much of the current antiviral research focuses on providing drugs with (i) improved oral bioavailability and pharmacokinetics which permit less frequent oral or topical dosing for suppressive treatment of herpes simplex virus (HSV) infections, (ii) different mechanisms of action for synergic effects in treating resistant HSV infections in the immunocompromised host and (iii) improved efficacy."( New therapeutic approaches to the alphaherpesvirus infections.
Cassady, KA; Whitley, RJ, 1997
)
0.3
" Absorption of L-FMAU after oral administration was incomplete, and bioavailability was approximately 20%."( Pharmacokinetics of 1-(2-fluoro-5-methyl-beta-L-arabinofuranosyl)uracil in woodchucks.
Ascenzi, MA; Baldwin, BH; Boudinot, FD; Chu, CK; Du, JF; Tennant, BC; Witcher, JW, 1997
)
0.3
" 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
" L-FMAU also has respectable bioavailability in rats."( Preclinical investigation of L-FMAU as an anti-hepatitis B virus agent.
Boudinot, FD; Cheng, YC; Choi, Y; Chu, CK; Cote, PJ; Gerin, JL; Hong, JH; Korba, BE; Peek, SF; Tennant, BC, 1998
)
0.3
" This appears to be the result of improved metabolic bioavailability of cytoplasmically retargeted mutant HSV1-tk/GFP enzymes for reaction with the radiolabeled probe (e."( Cytoplasmically retargeted HSV1-tk/GFP reporter gene mutants for optimization of noninvasive molecular-genetic imaging.
Ageyeva, L; Balatoni, J; Beresten, T; Blasberg, R; Doubrovin, M; Ponomarev, V; Serganova, I; Shavrin, A; Tjuvajev, JG; Vider, J,
)
0.13

Dosage Studied

ExcerptRelevanceReference
" The ascending dosage studies have been analyzed by the BV-araU RIA, and results indicate that the values of area under the serum concentration-time curve increased proportionally with the administered dose of BV-araU up to 80 mg."( A radioimmunoassay for the new antiviral agent 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil.
Jagoda, E; Mantha, S; Ogan, M; Stouffer, B; Tsay, HM; Tu, JI; Turabi, N; Yost, F, 1992
)
0.28
"6 microM at 6 h after dosing are in the range of the effective antiviral concentration for FEAU."( Preclinical pharmacology and pharmacokinetics of the anti-hepatitis virus agent 2'-fluoro-5-ethyl-1-beta-D-arabinofuranosyluracil in mice and rats.
Chiang, J; Chou, TC; Gloff, CA; Kong, XB; Tong, WP; Vidal, P, 1992
)
0.28
" In the initial phase I trial neurotoxicity, characterized by extrapyramidal dysfunction, was found to be the dose-limiting toxic effect, and a dosage of 32 mg/m2/day for 5 days was suggested for phase II studies."( Phase I trial of 1-(2'-deoxy-2'-fluoro-1-beta-D-arabinofuranosyl)-5-methyluracil (FMAU) terminated by severe neurologic toxicity.
Abbruzzese, JL; Castellanos, AM; Krakoff, IH; Legha, SS; Levy, JK; Raber, MN; Schmidt, S, 1989
)
0.28
" 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
" There was a lag of at least 5 h after dosing with 882C87 before 5PU was detectable in plasma."( Pharmacokinetics and tolerability of single oral doses of 882C87, a potent, new anti-varicella-zoster virus agent, in healthy volunteers.
Crome, P; Holdich, TA; Peck, RW; Posner, J; Weatherley, BC; Wootton, R, 1995
)
0.29
" This new drug produces enhanced plasma levels of acyclovir following oral dosing, which will not only allow more convenient dosing for the treatment of herpes simplex virus and varicella zoster virus (VZV) infections, but also mean that valaciclovir has the potential for superior clinical efficacy over acyclovir."( Acyclovir--and beyond.
Darby, G, 1994
)
0.29
" However, E-5-(2-bromovinyl)uracil (BVU) is the major metabolite found after oral dosing in animals other than mice."( Metabolism of 5'-ether prodrugs of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil in rats.
Ashida, N; Ijichi, K; Machida, H; Watanabe, Y, 1993
)
0.29
"Netivudine dosing produces complete inhibition of plasma dihydropyrimidine dehydrogenase."( Inhibition of dihydropyrimidine dehydrogenase by 5-propynyluracil, a metabolite of the anti-varicella zoster virus agent netivudine.
Callaghan, J; Crome, P; Fraser, I; Frick, L; Peck, R; Posner, J; Wiggs, R; Wootton, R, 1996
)
0.29
" Thus, the disposition of L-FMAU was linear over the dosage of 10 to 50 mg/kg."( Pharmacokinetics of 1-(2-deoxy-2-fluoro-beta-L-arabinofuranosyl)-5-methyluracil (L-FMAU) in rats.
Boudinot, FD; Chu, CK; Ma, T; Wright, JD, 1995
)
0.29
"The pharmacokinetics of L-FMAU in rats were independent of dose over the dosage range of 10 to 50 mg/kg."( Pharmacokinetics of 1-(2-deoxy-2-fluoro-beta-L-arabinofuranosyl)-5-methyluracil (L-FMAU) in rats.
Boudinot, FD; Chu, CK; Ma, T; Wright, JD, 1995
)
0.29
" These findings suggest that netivudine dosage may need to be reduced in patients with severe renal failure, and confirm that formation of the 5 PU is independent of the elimination of netivudine from plasma."( Pharmacokinetics of netivudine, a potent anti-varicella zoster virus drug, in patients with renal impairment.
Bidault, R; Chretien, P; Fillastre, JP; Gillotin, C; Godin, M; Legallicier, B; Peck, RW; Posner, J; Wooton, R, 1996
)
0.29
" Much of the current antiviral research focuses on providing drugs with (i) improved oral bioavailability and pharmacokinetics which permit less frequent oral or topical dosing for suppressive treatment of herpes simplex virus (HSV) infections, (ii) different mechanisms of action for synergic effects in treating resistant HSV infections in the immunocompromised host and (iii) improved efficacy."( New therapeutic approaches to the alphaherpesvirus infections.
Cassady, KA; Whitley, RJ, 1997
)
0.3
" With the completion of the first efficacy trials for each of these agents it has become apparent that, whilst less frequent dosing can he accomplished, it is not easy to significantly improve on the efficacy of aciclovir."( Antiviral drugs in development for herpes zoster.
Fiddian, AP, 1996
)
0.29
" In one study, healthy volunteers received an initial, single dose followed, a week later, by repeat dosing for 9 1/2 days; in the other, patients with shingles were treated for 8 days and data were also recorded for rash resolution and pain duration and intensity."( Multiple dose netivudine, a potent anti-varicella zoster virus agent, in healthy elderly volunteers and patients with shingles.
Bannister, B; Crome, P; Crooks, RJ; Mandal, BK; McKendrick, MW; Peck, RW; Wood, MJ, 1996
)
0.29
" All of these rats died within 10 days, whereas rats given SRV or tegafur alone under the same dosage conditions showed no appreciable change over 20 days compared with controls."( A possible mechanism of eighteen patient deaths caused by interactions of sorivudine, a new antiviral drug, with oral 5-fluorouracil prodrugs.
Kato, A; Ogura, K; Okuda, H; Takubo, H; Watabe, T, 1998
)
0.3
" L(-)I-OddU is the most potent anti-Epstein-Barr Virus (EBV) compound without cytotoxicity and animal toxicity upon long-term dosing which gives the pharmacological levels of the drug in plasma."( Potential use of antiviral L(-)nucleoside analogues for the prevention or treatment of viral associated cancers.
Cheng, YC, 2001
)
0.31
" In the present study, we evaluated the safety and efficacy of clevudine 30 mg daily for 24 weeks and assessed the durability of antiviral response for 24 weeks after cessation of dosing in hepatitis B e antigen (HBeAg)-negative chronic hepatitis B (e-CHB)."( Clevudine is highly efficacious in hepatitis B e antigen-negative chronic hepatitis B with durable off-therapy viral suppression.
Byun, KS; Cho, M; Cho, SH; Choi, JY; Choi, SK; Chon, CY; Chung, YH; Han, BH; Han, JY; Hwang, JS; Hwang, SG; Jeong, SH; Kim, BI; Kim, DG; Kim, HC; Kim, JH; Kim, TH; Kim, YS; Koh, KC; Kweon, YO; Lee, HJ; Lee, HS; Lee, HY; Lee, KS; Lee, MS; Lee, YJ; Lee, YS; Park, JW; Ryu, SH; Um, SH; Yang, JM; Yoo, BC; Yoo, HW; Yoo, K, 2007
)
0.34
"Clevudine appears to be a potent and tolerable (over 12 weeks) anti-viral and the optimal dosage appears to be 30 mg once daily."( Clinical trial: a phase II, randomized study evaluating the safety, pharmacokinetics and anti-viral activity of clevudine for 12 weeks in patients with chronic hepatitis B.
Blum, MR; Hann, HW; Lau, GK; Leung, N; Lim, SG; Marcellin, P; Mommeja-Marin, H; Moxham, C; Rousseau, F; Snow, A; Sorbel, J; Trepo, C, 2008
)
0.35
"These results are consistent with once daily CLV dosing currently being used in Phase III clinical studies."( Clevudine is efficiently phosphorylated to the active triphosphate form in primary human hepatocytes.
Furman, PA; Murakami, E; Niu, C, 2008
)
0.35
"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
" There are marked differences in drug dosing and scheduling depending on the protocols when treating AML patients with AraC."( Simultaneous determination of cytosine arabinoside and its metabolite uracil arabinoside in human plasma by LC-MS/MS: Application to pharmacokinetics-pharmacogenetics pilot study in AML patients.
Berda-Haddad, Y; Ciccolini, J; Costello, R; Donnette, M; Fanciullino, R; Farnault, L; Giocanti, M; Hau, LTT; Lacarelle, B; Ouafik, L; Solas, C; Venton, G, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (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 (44)

Assay IDTitleYearJournalArticle
AID587231Cytotoxicity against human MCF7 cells assessed as cell growth inhibition at 20 ug/ml after 72 hrs by sulforhodamine B assay2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Bioactive compounds from the fern Lepisorus contortus.
AID475458Antiviral activity against HIV1 3B infected human CEM cells assessed as inhibition of syncytia formation after 4 days2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID475470Antiviral activity against HSV1 KOS assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID1136033Inhibition of Herpesvirus 1 pyrimidine 2'-deoxyribonucleoside kinase by double reciprocal plot analysis in presence of thymidine1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Antiviral and antineoplastic activities of pyrimidine arabinosyl nucleosides and their 5'-amino derivatives.
AID1123259Cytotoxicity against primary rabbit kidney cells assessed as change in cell morphology1979Journal of medicinal chemistry, Mar, Volume: 22, Issue:3
5-Substituted uracil arabinonucleosides as potential antiviral agents.
AID475463Cytostatic activity mouse L1210 cells2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID1123319Antiviral activity against Vaccinia virus infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity treated immediately after virus adsorption measured 2 to 3 days after virus infection1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Synthesis and antiviral activities of arabinofuranosyl-5-ethylpyrimidine nucleosides. Selective antiherpes activity of 1-(beta-D-arabinofuranosyl)-5-ethyluracil.
AID475478Antiviral activity against Sindbis virus assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID587227Inhibition of ovine COX1 assessed as PGE2 formation at 10 ug/ml by LC-MS-MS analysis2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Bioactive compounds from the fern Lepisorus contortus.
AID475477Antiviral activity against Reovirus 1 assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID587230Cytotoxicity against mouse Hepa-1c1c7 cells assessed as cell growth inhibition at 20 ug/ml after 72 hrs by sulforhodamine B assay2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Bioactive compounds from the fern Lepisorus contortus.
AID475474Antiviral activity against Respiratory syncytial virus Long assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID1123324Antiviral activity against Herpes simplex virus-2 196 infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity treated immediately after virus adsorption measured 2 to 3 days after virus infection1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Synthesis and antiviral activities of arabinofuranosyl-5-ethylpyrimidine nucleosides. Selective antiherpes activity of 1-(beta-D-arabinofuranosyl)-5-ethyluracil.
AID1123322Antiviral activity against Herpes simplex virus-1 KOS infected in human skin fibroblast cells assessed as inhibition of virus-induced cytopathogenicity treated immediately after virus adsorption measured 2 to 3 days after virus infection1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Synthesis and antiviral activities of arabinofuranosyl-5-ethylpyrimidine nucleosides. Selective antiherpes activity of 1-(beta-D-arabinofuranosyl)-5-ethyluracil.
AID587226Inhibition of NO production in mouse RAW264.7 cells at 20 ug/ml after 30 mins by Griess assay2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Bioactive compounds from the fern Lepisorus contortus.
AID475479Antiviral activity against Punta Toro virus assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID1123258Antiviral activity against HSV1 KOS infected in human skin fibroblasts assessed as inhibition of virus-induced cytopathogenicity1979Journal of medicinal chemistry, Mar, Volume: 22, Issue:3
5-Substituted uracil arabinonucleosides as potential antiviral agents.
AID475457Antiviral activity against HIV2 infected human CEM cells assessed as inhibition of syncytia formation after 4 days2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID475464Cytostatic activity human CEM cells2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID1123256Antiviral activity against Vesicular stomatitis virus infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity1979Journal of medicinal chemistry, Mar, Volume: 22, Issue:3
5-Substituted uracil arabinonucleosides as potential antiviral agents.
AID1879226Antiviral activity against HCV by replicon assay2022Bioorganic & medicinal chemistry letters, 04-01, Volume: 61Design, chemical synthesis and antiviral evaluation of 2'-deoxy-2'-fluoro-2'-C-methyl-4'-thionucleosides.
AID475459Cytostatic activity against human NB4 cells2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID475472Antiviral activity against Herpes simplex virus2 G assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID1123257Antiviral activity against Vaccinia virus infected in human skin fibroblasts assessed as inhibition of virus-induced cytopathogenicity1979Journal of medicinal chemistry, Mar, Volume: 22, Issue:3
5-Substituted uracil arabinonucleosides as potential antiviral agents.
AID475461Cytostatic activity human KG1 cells2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID475471Antiviral activity against thymidine kinase deficient acyclovir resistant HSV1 KOS assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID475480Antiviral activity against influenza A virus H1N1 assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID587228Inhibition of human COX2 assessed as PGE2 formation at 10 ug/ml by LC-MS-MS analysis2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Bioactive compounds from the fern Lepisorus contortus.
AID475481Antiviral activity against influenza A virus H3N2 assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID475462Cytostatic activity human U937 cells2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID1123320Antiviral activity against Vaccinia virus infected in human skin fibroblast cells assessed as inhibition of virus-induced cytopathogenicity treated immediately after virus adsorption measured 2 to 3 days after virus infection1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Synthesis and antiviral activities of arabinofuranosyl-5-ethylpyrimidine nucleosides. Selective antiherpes activity of 1-(beta-D-arabinofuranosyl)-5-ethyluracil.
AID1123260Cytotoxicity against human skin fibroblasts assessed as change in cell morphology1979Journal of medicinal chemistry, Mar, Volume: 22, Issue:3
5-Substituted uracil arabinonucleosides as potential antiviral agents.
AID475475Antiviral activity against Vesicular stomatitis virus assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID1123326Antimetabolic activity against primary rabbit kidney cells assessed as inhibition of [2-14C]dUrd incorporation into DNA after 16 hrs1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Synthesis and antiviral activities of arabinofuranosyl-5-ethylpyrimidine nucleosides. Selective antiherpes activity of 1-(beta-D-arabinofuranosyl)-5-ethyluracil.
AID1123321Antiviral activity against Herpes simplex virus-1 KOS infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity treated immediately after virus adsorption measured 2 to 3 days after virus infection1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Synthesis and antiviral activities of arabinofuranosyl-5-ethylpyrimidine nucleosides. Selective antiherpes activity of 1-(beta-D-arabinofuranosyl)-5-ethyluracil.
AID475473Antiviral activity against Vaccinia virus lederle assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID475482Antiviral activity against Human parainfluenza virus 3 assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID1123325Antimetabolic activity against primary rabbit kidney cells assessed as inhibition of [methyl-3H]dThd incorporation into DNA after 16 hrs1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Synthesis and antiviral activities of arabinofuranosyl-5-ethylpyrimidine nucleosides. Selective antiherpes activity of 1-(beta-D-arabinofuranosyl)-5-ethyluracil.
AID1123255Antiviral activity against HSV1 KOS infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity1979Journal of medicinal chemistry, Mar, Volume: 22, Issue:3
5-Substituted uracil arabinonucleosides as potential antiviral agents.
AID1123254Antiviral activity against Vaccinia virus infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity1979Journal of medicinal chemistry, Mar, Volume: 22, Issue:3
5-Substituted uracil arabinonucleosides as potential antiviral agents.
AID1123318Antiviral activity against Vesicular stomatitis virus infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity treated immediately after virus adsorption measured 2 to 3 days after virus infection1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Synthesis and antiviral activities of arabinofuranosyl-5-ethylpyrimidine nucleosides. Selective antiherpes activity of 1-(beta-D-arabinofuranosyl)-5-ethyluracil.
AID1123323Antiviral activity against Herpes simplex virus-2 LYONS infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity treated immediately after virus adsorption measured 2 to 3 days after virus infection1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Synthesis and antiviral activities of arabinofuranosyl-5-ethylpyrimidine nucleosides. Selective antiherpes activity of 1-(beta-D-arabinofuranosyl)-5-ethyluracil.
AID475460Cytostatic activity against human HL60 cells2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
AID475476Antiviral activity against Coxsackievirus B4 assessed as inhibition of virus-induced cytopathicity by cell based assay2010Bioorganic & medicinal chemistry, Apr-01, Volume: 18, Issue:7
Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (586)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990128 (21.84)18.7374
1990's197 (33.62)18.2507
2000's163 (27.82)29.6817
2010's93 (15.87)24.3611
2020's5 (0.85)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 (%)
Trials0 (0.00%)5.53%
Trials43 (7.14%)5.53%
Reviews0 (0.00%)6.00%
Reviews51 (8.47%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies22 (3.65%)4.05%
Observational0 (0.00%)0.25%
Observational1 (0.17%)0.25%
Other6 (100.00%)84.16%
Other485 (80.56%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]