Page last updated: 2024-12-06

5-propynylarabinofuranosyluracil

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

Description

5-propynylarabinofuranosyluracil: potent inhibitor of VZV [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID55281
CHEMBL ID1097615
SCHEMBL ID1585773
MeSH IDM0185870

Synonyms (30)

Synonym
pyarau
84558-93-0
882c87
netivudine
1-.beta.-d-arabinofuranosyl-5-(1-propynyl)uracil
1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-prop-1-ynyl-pyrimidine-2,4-dione
CHEMBL1097615
882c-87
1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-prop-1-ynylpyrimidine-2,4-dione
2,4(1h,3h)-pyrimidinedione, 1-beta-d-arabinofuranosyl-5-(1-propynyl)-
unii-f7k51t0q1w
bw882c87
1-beta-d-arabinofuranosyl-5-(1-propynyl)uracil
drg-0179
1-(beta-d-arabinofuranosyl)-5-(1-propynyl)uracil
netivudine [inn:ban]
f7k51t0q1w ,
5-propynylarabinofuranosyluracil
netivudine [mart.]
netivudine [inn]
netivudine [who-dd]
SCHEMBL1585773
DTXSID70233545
QLOCVMVCRJOTTM-SDNRWEOFSA-N
1-(beta-d-arabinofuranosyl)-5-propynyluracil
DB12606
Q27277769
HY-105102
CS-0025006
1-((2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(prop-1-yn-1-yl)pyrimidine-2,4(1h,3h)-dione

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" 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
" 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

Bioavailability

ExcerptReferenceRelevance
" 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

Dosage Studied

ExcerptRelevanceReference
" 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
"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
" 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
" 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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID476929Human intestinal absorption in po dosed human2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Neural computational prediction of oral drug absorption based on CODES 2D descriptors.
AID592681Apparent permeability across human Caco2 cell membrane after 2 hrs by LC-MS/MS analysis2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
QSAR-based permeability model for drug-like compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's18 (81.82)18.2507
2000's2 (9.09)29.6817
2010's2 (9.09)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: 10.77

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

MetricThis Compound (vs All)
Research Demand Index10.77 (24.57)
Research Supply Index3.37 (2.92)
Research Growth Index4.14 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.77)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (27.27%)5.53%
Reviews7 (31.82%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (40.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
A Double-Blind, Multicenter Study Comparing Oral 882C87 With Oral Acyclovir for Treatment of Localized Herpes Zoster in Immunocompromised Patients [NCT00002315]Phase 3400 participants InterventionalCompleted
[information is prepared from clinicaltrials.gov, extracted Sep-2024]