Page last updated: 2024-12-06

dexelvucitabine

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

Description

dexelvucitabine: inhibits human hepatitis B virus (HBV) and human immunodeficiency virus (HIV) in vitro [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID64973
CHEMBL ID109831
SCHEMBL ID599014
MeSH IDM0260905

Synonyms (47)

Synonym
psi-5582
reverset
beta-d-d4fc
dpc-817
incb-8721
yz-817
D06580
reverset (tn)
dexelvucitabine (usan/inn)
dfc
dpc 817
4-amino-5-fluoro-1-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one
d4fc
134379-77-4
.beta.-d-d4fc
rvt
.beta.-d-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine
reverset (tm)
d-d4fc
dexelvucitabine
ra 131423
5f-d4c
CHEMBL109831
2',3'-dideoxy-2',3'-didehydro-beta-l-5-fluorocytidine
unii-ku8spj271w
ku8spj271w ,
2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine
cytidine, 2',3'-didehydro-2',3'-dideoxy-5-fluoro-
yz 817
incb 8721
dexelvucitabine [usan:inn]
doc 817
(+)-4-amino-5-fluoro-1-((2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)pyrimidin-2(1h)-one
SCHEMBL599014
dexelvucitabine [usan]
cytidine, 2',3'-didehydro-2',3'-dideoxy-5-fluoro
dexelvucitabine [inn]
dexelvucitabine [who-dd]
DTXSID20158678
reverse-t
AKOS030568059
DB12470
Q5268320
4-amino-5-fluoro-1-((2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)pyrimidin-2(1h)-one
MS-23285
HY-14920
CS-0003633

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"The values of the pharmacokinetic parameters of the nucleoside antiretroviral agent beta-D-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine (D-D4FC) in rhesus monkeys were determined with a two-compartment model after the administration of a single dose."( Pharmacokinetics of the antiviral agent beta-D-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine in rhesus monkeys.
Hurwitz, SJ; Liotta, DC; Ma, L; Mcatee, JJ; McClure, HM; Schinazi, RF; Shi, J, 1999
)
0.3
" The pharmacokinetic behavior of elvucitabine was best described by a two-compartment linear model using two absorption rates and a first-order elimination rate."( Effect of a single dose of ritonavir on the pharmacokinetic behavior of elvucitabine, a nucleoside reverse transcriptase inhibitor, administered in healthy volunteers.
Colucci, P; Ducharme, MP; Pottage, JC; Robison, H; Turgeon, J, 2009
)
0.35

Compound-Compound Interactions

ExcerptReferenceRelevance
" Additive antiviral activity was observed with L(-)Fd4C in combination with 2',3'-dideoxycytidine (ddC, or zalcitabine) or 2',3'-dideoxyinosine (ddI, or didanosine)."( Metabolism of 2',3'-dideoxy-2',3'-didehydro-beta-L(-)-5-fluorocytidine and its activity in combination with clinically approved anti-human immunodeficiency virus beta-D(+) nucleoside analogs in vitro.
Bridges, EG; Cheng, YC; Dutschman, GE; Gullen, E; Guo, X; Kukhanova, M; Liu, SH, 1998
)
0.3

Bioavailability

ExcerptReferenceRelevance
" The oral bioavailability of D-D4FC averaged 41%."( Pharmacokinetics of the antiviral agent beta-D-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine in rhesus monkeys.
Hurwitz, SJ; Liotta, DC; Ma, L; Mcatee, JJ; McClure, HM; Schinazi, RF; Shi, J, 1999
)
0.3
" The decrease in elvucitabine bioavailability when elvucitabine was coadministered with ritonavir may be due to ritonavir's inhibiting influx gut transporters."( Effect of a single dose of ritonavir on the pharmacokinetic behavior of elvucitabine, a nucleoside reverse transcriptase inhibitor, administered in healthy volunteers.
Colucci, P; Ducharme, MP; Pottage, JC; Robison, H; Turgeon, J, 2009
)
0.35

Dosage Studied

ExcerptRelevanceReference
" 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
" These results indicate that beta-L-Fd4C exhibits a more potent antiviral effect than lamivudine in the WHV model but was not able to eradicate CCC DNA and infected cells from the liver at the dosage and with the protocol used."( Antiviral activity of beta-L-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine in woodchucks chronically infected with woodchuck hepatitis virus.
Cheng, YC; Chevallier, M; Guerret, S; Hantz, O; Jamard, C; King, I; Le Guerhier, F; Peyrol, S; Pichoud, C; Trépo, C; Zoulim, F, 2001
)
0.31
" Sequence analysis of the HIV-1 RT gene performed before and after RVT dosing detected no genotypic changes in this short-term study."( Potent antiviral effect of reverset in HIV-1-infected adults following a single oral dose.
Beard, A; Cartee, L; De La Rosa, A; Kravec, I; McBrayer, TR; Murphy, RL; Otto, MJ; Schinazi, RF; Schürmann, D; Stuyver, LJ, 2004
)
0.32
" Three different dosing regimens of elvucitabine were administered with lopinavir-ritonavir to 24 subjects with moderate levels of HIV."( Multiple-dose pharmacokinetic behavior of elvucitabine, a nucleoside reverse transcriptase inhibitor, administered over 21 days with lopinavir-ritonavir in human immunodeficiency virus type 1-infected subjects.
Colucci, P; Ducharme, MP; Hoepelman, IM; Pottage, JC; Robison, H; Schürmann, D; Turgeon, J, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID86696Tested in vitro for anticancer activity against HepG2 cells1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.
AID8449Tested in vitro for anticancer activity against 9L cells; Not determined1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.
AID152632Tested in vitro for anti HIV-1 activity against PBM cells1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.
AID156334Tested in vitro for anticancer activity against PC-3 cells1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.
AID323397Antiviral activity against HIV1 LAI in human PBM cells2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Antiviral and cellular metabolism interactions between Dexelvucitabine and lamivudine.
AID104418In vitro inhibitory activity against growth of HIV infected MT-2/IIIB cell line1998Bioorganic & medicinal chemistry letters, Nov-17, Volume: 8, Issue:22
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.
AID152625Tested in vitro for anti HIV-1 activity against PBM cells1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.
AID323405Reduction in Lamivudine diphosphate choline level in human CEM cells2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Antiviral and cellular metabolism interactions between Dexelvucitabine and lamivudine.
AID201986Tested in vitro for anticancer activity against SK-MEL-28 cells1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.
AID102615Tested in vitro for anticancer activity against MCF-7 cells1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.
AID323400Reduction of Lamivudine triphosphate level at 100 uM in human CEM cells2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Antiviral and cellular metabolism interactions between Dexelvucitabine and lamivudine.
AID79637In vitro inhibitory activity against proliferation of HBV viral cell1998Bioorganic & medicinal chemistry letters, Nov-17, Volume: 8, Issue:22
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.
AID46571In vitro inhibitory activity against growth of HIV infected CEM cells combined with murine CTLL-2T lymphoblast cell line1998Bioorganic & medicinal chemistry letters, Nov-17, Volume: 8, Issue:22
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.
AID323403Reduction in Lamivudine metabolite level in human CEM cells at 33.3 uM2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Antiviral and cellular metabolism interactions between Dexelvucitabine and lamivudine.
AID216188Tested in vitro for cytotoxicity against Vero cells1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.
AID83235In vitro inhibitory activity against proliferation of HIV viral cell1998Bioorganic & medicinal chemistry letters, Nov-17, Volume: 8, Issue:22
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.
AID323404Reduction in Lamivudine metabolite level in human CEM cells at 100 uM2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Antiviral and cellular metabolism interactions between Dexelvucitabine and lamivudine.
AID202327Tested in vitro for anticancer activity against SK-MES-1 cells1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.
AID323401Reduction of Lamivudine triphosphate level at 100 uM in human PBMC2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Antiviral and cellular metabolism interactions between Dexelvucitabine and lamivudine.
AID152794Tested in vitro for cytotoxicity against PBM cells1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.
AID47449Tested in vitro for anticancer activity against CEM cells1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.
AID100403Tested in vitro for anticancer activity against LNCaP cells1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.
AID197123In vitro inhibitory activity against growth of HIV infected Rat-1 cell line1998Bioorganic & medicinal chemistry letters, Nov-17, Volume: 8, Issue:22
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.
AID86396In vitro inhibitory activity against growth of HIV infected HepG2 cell line1998Bioorganic & medicinal chemistry letters, Nov-17, Volume: 8, Issue:22
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.
AID39131In vitro inhibitory activity against growth of HIV infected B16 cell line1998Bioorganic & medicinal chemistry letters, Nov-17, Volume: 8, Issue:22
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.
AID46570In vitro inhibitory activity against growth of HIV infected CEM cell line1998Bioorganic & medicinal chemistry letters, Nov-17, Volume: 8, Issue:22
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.
AID53792In vitro inhibitory activity against growth of HIV infected DLD-1 cell line1998Bioorganic & medicinal chemistry letters, Nov-17, Volume: 8, Issue:22
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.
AID323402Reduction in Lamivudine metabolite level in human CEM cells at 1 uM2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Antiviral and cellular metabolism interactions between Dexelvucitabine and lamivudine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (38)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's8 (21.05)18.2507
2000's28 (73.68)29.6817
2010's2 (5.26)24.3611
2020's0 (0.00)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 (%)
Trials3 (7.89%)5.53%
Reviews5 (13.16%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other30 (78.95%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (10)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
14-Day Randomized Double-Blind Comparative Viral Kinetic Study of Elvucitabine Versus Lamivudine Once Daily to HIv-1 Subjects With M184V [NCT00405249]Phase 25 participants (Anticipated)Interventional2006-09-30Completed
A Double-blind, Randomized, Placebo-controlled Trial to Evaluate the Safety and Efficacy of 12 Weeks Oral Treatment With ACH126, 433 (b-L-Fd4C) in Adults With Lamivudine-resistant Chronic Hepatitis B [NCT00040144]Phase 285 participants Interventional2002-07-31Terminated(stopped due to Safety concerns)
An Open-Label Treatment Protocol to Provide Continued ACH-126,443 to Subjects of Previous Achillion-Sponsored Phase 1 and 2 Studies in Chronic Hepatitis B Infection [NCT00037622]100 participants InterventionalTerminated(stopped due to Safety concerns from other studies.)
A Phase 2 Trial of 4 Weeks of ACH-126,443 in Comparison With Continued Lamivudine in Stable Triple Antiretroviral Combination Therapy in HIV-Infected Subjects With Modestly Detectable Viral Load [NCT00040157]Phase 260 participants InterventionalTerminated(stopped due to Safety concerns)
A Placebo-Controlled, Dose-Escalation Study in HIV-1 Infected Subjects to Characterize the Safety, Tolerability, and Pharmacokinetics of Single Oral Doses of DPC 817 [NCT00040274]Phase 130 participants InterventionalCompleted
A Randomized, Double-Blind, Phase II Study Comparing the Anti-Retroviral Safety and Efficacy of Dexelvucitabine (DFC) 200 mg Once Daily to Lamivudine (3TC) 300 mg Once Daily in Addition to Optimized Background Therapy in HIV-1 Infected Subjects Who Have F [NCT00300573]Phase 2250 participants (Actual)Interventional2006-04-30Terminated(stopped due to Development program ended due to inability to pair with other cytidine analogs and higher risk of hyperlipasemia when not used with 3TC/FTC.)
An Open-Label Treatment Protocol to Provide Continued Elvucitabine Treatment for 48 Weeks in Participants Who Have Completed 96 Weeks of Elvucitabine Therapy in Protocol ACH443-015 or 48 Weeks of Therapy in Protocol ACH443-018 [NCT00675844]Phase 27 participants (Actual)Interventional2008-05-31Completed
An Open-Label, 48-Week Extension Study of Elvucitabine Administered In Combination With Background Antiretroviral Agents in Participants Who Have Completed 14 Days of Treatment in Protocol ACH443-014A. [NCT00380159]Phase 24 participants (Actual)Interventional2006-09-30Completed
A Randomized, Blinded, 12-week Comparison of Elvucitabine/Efavirenz/Tenofovir Versus Lamivudine/Efavirenz/Tenofovir in HIV-1 Infected Treatment-naive Participants. There is a 36 Week, Open-label, Extension Phase for Eligible Participants. [NCT00350272]Phase 276 participants (Actual)Interventional2006-05-31Completed
A 14 Day Randomized, Double-blind, Study of Once Daily Elvucitabine Versus Lamivudine in Participants With a Documented M184V Mutation [NCT00312039]Phase 1/Phase 220 participants (Anticipated)Interventional2006-03-31Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT00350272 (2) [back to overview]The Proportion Of Participants With Virologic Response For 10 mg/Day Elvucitabine In HIV-1-Infected Participants By 12 Weeks Compared With The Proportion Of Participants With Lamivudine 300 mg/Day
NCT00350272 (2) [back to overview]The Safety Profile Of Elvucitabine.

The Proportion Of Participants With Virologic Response For 10 mg/Day Elvucitabine In HIV-1-Infected Participants By 12 Weeks Compared With The Proportion Of Participants With Lamivudine 300 mg/Day

The proportion of participants having achieved a virologic response for elvucitabine 10 mg/day in combination with efavirenz and tenofovir in HIV-1-infected participants over 12 weeks compared with the proportion of participants having achieved a virologic response for lamivudine 300 mg/day in combination with efavirenz and tenofovir. Virologic response was defined as having achieved undetectable (<50 copies/mL) HIV-1 RNA levels from baseline assessment. (NCT00350272)
Timeframe: 12 weeks

,
Interventionpercentage of participants (Number)
Week 2Week 4Week 6Week 8Week 10Week 12
Elvucitabine13.516.227.035.154.156.8
Lamivudine8.110.835.154.156.870.3

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The Safety Profile Of Elvucitabine.

Determination of the safety profile of elvucitabine as defined by the frequency, type and severity of treatment-emergent adverse events (AEs) and the frequency of Grade 3 and Grade 4 laboratory abnormalities. (NCT00350272)
Timeframe: 12 weeks

,
Interventionparticipants (Number)
Treatment emergent adverse eventsTreatment emergent severe adverse eventsTreatment related serious adverse eventsDiscontinuations due to adverse eventsTreatment emergent Grade 3/4 lab abnormalities
Elvucitabine, Efavirenz,Tenofovir363026
Lamivudine,Efavirenz,Tenofovir352005

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