Compounds > lodenosine
Page last updated: 2024-12-06

lodenosine

Description

lodenosine: anti-HIV nucleoside analog, the flourine atom on lodenosine is located at 2-arabinoside location, while 2'-fluoro-2',3'-dideoxyadenosine has the flourine residue at the 2-ribose sugar location [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72180
CHEMBL ID501916
SCHEMBL ID97908
MeSH IDM0197703

Synonyms (46)

Synonym
nsc-613792
lodenosine
ddg-1
nsc 613792
2'-fdda
2'-beta-fluoro-2',3'-dideoxyadenosine
9h-purin-6-amine, 9-(2,3-dideoxy-2-fluoro-beta-d-threo-pentofuranosyl)-
lodenosine [usan]
drg-0246
9-(2,3-dideoxy-2-fluoro-beta-d-threo-pentofuranosyl) adenine
9-(2,3-dideoxy-2-fluoro-beta-d-threo-pentofuranosyl)-9h-purin-6-amine
lodenosine (usan)
D04759
9-(2-fluoro-2,3-dideoxy-.beta.-d-threo-pentofuranosyl)adenine
[(2s,4s,5r)-5-(6-aminopurin-9-yl)-4-fluoro-tetrahydrofuran-2-yl]methanol
fdda
2'-fdda (*.beta.-d-threo*)
2'-f-dd-ara-a
2'-fddaraa
f-dda
lodenosine (tm)
f.beta.dda
f-ddado
nsc674668
110143-10-7
CHEMBL501916
lodenosine [usan:inn]
3wb2lgt4r1 ,
ccris 9418
unii-3wb2lgt4r1
lodenosine [who-dd]
9h-purin-6-amine, 9-(2,3-dideoxy-2-fluoro-.beta.-d-threo-pentofuranosyl)-
9-(2,3-dideoxy-2-fluoro-.beta.-d-threo-pentofuranosyl) adenine
2'-.beta.-fluoro-2',3'-dideoxyadenosine
lodenosine [inn]
SCHEMBL97908
((2s,4s,5r)-5-(6-amino-9h-purin-9-yl)-4-fluoro-tetrahydrofuran-2-yl)methanol
6-amino-9-(2 3-dideoxy-2 fluoro-beta-d-arabinofuranosyl)-9h-purine
KBEMFSMODRNJHE-JFWOZONXSA-N
6-amino-9-(2,3-dideoxy-2-fluoro-beta-d-arabinofuranosyl)-9h-purine
9-(2,3-dideoxy-2-fluoro-beta-d-threo- pentofuranosyl)-9h-purine-6-amine
((2s,4s,5r)-5-(6-amino-9h-purin-9-yl)-4-fluorotetrahydrofuran-2-yl)methanol
9-(2,3-dideoxy-2-fluoro-alpha-d-threopentofuranosyl)-adenine
DTXSID90149154
Q6666263
AKOS040744415

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"A single and multiple dose pharmacokinetic (PK) study was conducted in rats following oral administration of 2'-fluoro-2',3'-dideoxyadenosine (FddA) and 2'-fluoro-2',3'-dideoxyinosine (FddI) at three dose levels."( Single dose and multiple dose pharmacokinetics of 2'-fluoro-2',3'-dideoxyadenosine and 2'-fluoro-2',3'-dideoxyinosine, anti-HIV agents, in rats.
Shyu, WC; Srinivas, NR, )		0.13

Bioavailability

ExcerptReferenceRelevance
"Intestinal enzyme inhibition may be an effective tool to increase the oral bioavailability of compounds that undergo first-pass intestinal metabolism."( Enhanced oral bioavailability of 2'- beta-fluoro-2',3'-dideoxyadenosine (F-ddA) through local inhibition of intestinal adenosine deaminase.
Anderson, BD; DeGraw, RT, 2001)		0.31
"5 microg/ml could achieve an intestinal bioavailability of 80% with <20% systemic inhibition."( Enhanced oral bioavailability of 2'- beta-fluoro-2',3'-dideoxyadenosine (F-ddA) through local inhibition of intestinal adenosine deaminase.
Anderson, BD; DeGraw, RT, 2001)		0.31

Dosage Studied

ExcerptRelevanceReference
"5-fold reduction in optimal ddIno dosage with no decrease in therapeutic effect or increase in toxicity."( Enhancement by hydroxyurea of the anti-human immunodeficiency virus type 1 potency of 2'-beta-fluoro-2',3'-dideoxyadenosine in peripheral blood mononuclear cells.
Driscoll, JS; Gao, WY; Johns, DG; Mitsuya, H, 1995)		0.29
" This study explores various factors involved in inhibitor selection and dosage regimen design to achieve local ADA inhibition with minimal systemic inhibition."( Enhanced oral bioavailability of 2'- beta-fluoro-2',3'-dideoxyadenosine (F-ddA) through local inhibition of intestinal adenosine deaminase.
Anderson, BD; DeGraw, RT, 2001)		0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (70)

Assay IDTitleYearJournalArticle
AID233539The ratio of AUC / dose (mM.h/uMol)/kg at 112 mg/kg dose after oral administration in mice brain; AUC/Dose (uM)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID47114Antiviral activity evaluated as the ability to inhibit the replication of HIV-2 in human T-lymphocytic cells (CEM)1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2'-fluoro-ara- and 2'-fluoro-ribo-2',3'- dideoxyadenosine as a strategy to bypass a metabolic blockade.
AID80897Ability to protect CD4+ ATH8 cells from cytopathogenic effects of HIV-1; No effect1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID79147Percentage of gag protein expression using H9 cells at 100 uM on 10th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID14760Pharmacokinetic parameter AUC was measured at 55 mg/kg dose by intravenous administration mice serum.; AUC 0-r (mM.h)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID79268Percentage of gag protein expression using H9 cells at 5 uM on 12th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID79263Percentage of gag protein expression using H9 cells at 20 uM on 7th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID22609Kinetic parameter Vmax at pH 7.4 and 37 degree Centigrade1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID105521Anti-HIV activity was determined as dose required to protect 50% of the HIV-infected MT-4 cells against destruction1987Journal of medicinal chemistry, Nov, Volume: 30, Issue:11
Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis.
AID199981Inhibition of HIV-1 reverse transcriptase; + = active1994Journal of medicinal chemistry, Aug-05, Volume: 37, Issue:16
HIV-1 reverse transcriptase inhibitor design using artificial neural networks.
AID235639Selectivity index by CC50 of CEM cells/EC50 of CEM cells against HIV-11999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2'-fluoro-ara- and 2'-fluoro-ribo-2',3'- dideoxyadenosine as a strategy to bypass a metabolic blockade.
AID32056Anti-HIV activity (% toxicity) in ATH-8 cells at 5 uM in absence of 2'-deoxycoformycin at 0 uM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID14893Pharmacokinetic parameters was measured at 55 mg/kg dose by oral administration in mice serum.; AUC 0-r (mM.h)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID14750Pharmacokinetic parameter AUC was measured at 20 mg/kg dose by intravenous administration in mice serum; AUC 0-r (mM.h).1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID23368Hydrolysis half life in phosphate buffer; Not available1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2'-fluoro-ara- and 2'-fluoro-ribo-2',3'- dideoxyadenosine as a strategy to bypass a metabolic blockade.
AID31914Anti-HIV activity (% protection) in ATH-8 cells at 5 uM in presence of 2'-deoxycoformycin at 0 uM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID79149Percentage of gag protein expression using H9 cells at 100 uM on 7th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID233538The ratio of AUC / dose (mM.h/uMol)/kg at 112 mg/kg dose after intravenous administration in mice serum; AUC/Dose (uM)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID79271Percentage of gag protein expression using H9 cells at 50 uM on 12th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID24525t1/2 was measured AT 55 mg/Kg dose by intravenous administration in mice brain; t1/2 (h)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID24533t1/2 was measured at 55 mg/kg dose by intravenous administration in mice serum; t1/2 (h)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID14747Pharmacokinetic parameter AUC was measured at 20 mg/kg dose by intravenous administration in mice serum; AUC 0-r (mM.h)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID397592Therapeutic index, ratio of cytotoxicity against human H9 cells to EC50 for HIV1 RF2001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
AID79146Percentage of gag protein expression using H9 cells at 0 uM on 7th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID79144Percentage of gag protein expression using H9 cells at 0 uM on 10th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID24537t1/2 was measured at 55 mg/kg dose by oral administration in mice serum; t1/2 (h)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID79264Percentage of gag protein expression using H9 cells at 200 uM on 10th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID397589Antiviral activity against HIV1 3B in human H9 cells assessed as inhibition of virus-induced cytopathic effect by formazan-based conventional colorimetric technique2001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
AID31919Anti-HIV activity (% protection) in ATH-8 cells at 5 uM in presence of 2'-deoxycoformycin at 50 uM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID47112Antiviral activity evaluated as the ability to inhibit the replication of HIV-1 in human T-lymphocytic cells (CEM)1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2'-fluoro-ara- and 2'-fluoro-ribo-2',3'- dideoxyadenosine as a strategy to bypass a metabolic blockade.
AID79269Percentage of gag protein expression using H9 cells at 5 uM on 7th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID1254742Antiviral activity against HIV1 infected in human PBM cells assessed as inhibition of viral replication2015Journal of medicinal chemistry, Nov-12, Volume: 58, Issue:21
Applications of Fluorine in Medicinal Chemistry.
AID32058Anti-HIV activity (% toxicity) in ATH-8 cells at 5 uM in absence of 2'-deoxycoformycin at 50 uM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID32055Anti-HIV activity (% toxicity) in ATH-8 cells at 5 uM in presence of 2'-deoxycoformycin at 50 uM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID233536The ratio of AUC / dose (mM.h/uMol)/kg at 112 mg/kg dose after intravenous administration in mice brain; AUC/Dose (uM)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID79272Percentage of gag protein expression using H9 cells at 50 uM on 7th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID19629Partition coefficient (logP)1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2'-fluoro-ara- and 2'-fluoro-ribo-2',3'- dideoxyadenosine as a strategy to bypass a metabolic blockade.
AID397590Antiviral activity against HIV1 RF in human H9 cells assessed as inhibition of virus-induced cytopathic effect by formazan-based conventional colorimetric technique2001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
AID31922Anti-HIV activity (% protection) in ATH-8 cells at 5 uM in absence of 2'-deoxycoformycin at 50 uM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID24534t1/2 was measured at 55 mg/kg dose by oral administration in mice brain; t1/2 (h)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID32050Anti-HIV activity (% toxicity) in ATH-8 cells at 5 uM in presence of 2'-deoxycoformycin at 0 uM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID23289Partition coefficient (logP)1996Journal of medicinal chemistry, Apr-12, Volume: 39, Issue:8
Lipophilic, acid-stable, adenosine deaminase-activated anti-HIV prodrugs for central nervous system delivery. 3. 6-Amino prodrugs of 2'-beta-fluoro-2',3'-dideoxyinosine.
AID31921Anti-HIV activity (% protection) in ATH-8 cells at 5 uM in absence of 2'-deoxycoformycin at 20 uM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID31917Anti-HIV activity (% protection) in ATH-8 cells at 5 uM in presence of 2'-deoxycoformycin at 20 uM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID79145Percentage of gag protein expression using H9 cells at 0 uM on 12th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID79267Percentage of gag protein expression using H9 cells at 5 uM on 10th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID17445Kinetic parameter KM at pH 7.4 and 37 degree Centigrade1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID397591Therapeutic index, ratio of cytotoxicity against human H9 cells to EC50 for HIV1 3B2001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
AID79151Percentage of gag protein expression using H9 cells at 20 uM on 12th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID229420Selectivity ratio CD50 to ED501987Journal of medicinal chemistry, Nov, Volume: 30, Issue:11
Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis.
AID43988Effect of compound against Moloney murine sarcoma virus (MSV)-induced transformation of C3H/3T3 embryo murine fibroblasts1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2'-fluoro-ara- and 2'-fluoro-ribo-2',3'- dideoxyadenosine as a strategy to bypass a metabolic blockade.
AID79265Percentage of gag protein expression using H9 cells at 200 uM on 12th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID233535The ratio of AUC / dose (mM.h/uMol)/kg at 112 mg/kg dose after oral administration in mice serum; AUC/Dose (uM)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID14751Pharmacokinetic parameter AUC was measured at 20 mg/kg dose by oral administration in mice serum.; AUC 0-r (mM.h)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID44135Minimal cytotoxic concentration required to cause morphological alteration of C3H/3T3 fibroblast culture cells1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2'-fluoro-ara- and 2'-fluoro-ribo-2',3'- dideoxyadenosine as a strategy to bypass a metabolic blockade.
AID14746Pharmacokinetic parameter AUC was measured at 20 mg/kg dose by intravenous administration in mice brain; AUC 0-r (mM.h)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID14761Pharmacokinetic parameter AUC was measured at 55 mg/kg dose by oral administration in mice brain.; AUC 0-r (mM.h)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID32057Anti-HIV activity (% toxicity) in ATH-8 cells at 5 uM in absence of 2'-deoxycoformycin at 20 uM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID31920Anti-HIV activity (% protection) in ATH-8 cells at 5 uM in absence of 2'-deoxycoformycin at 0 uM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID14759Pharmacokinetic parameter AUC was measured at 55 mg/kg dose by intravenous administration in mice brain; AUC 0-r (mM.h)1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
In vitro and in vivo evaluation of 6-azido-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosylpurine and N6-methyl-2',3'-dideoxy-2'-fluoro-beta-D-arabinofuranosyladenine as prodrugs of the anti-HIV nucleosides 2'-F-ara-ddA and 2'-F-ara-ddI.
AID155282Anti-HIV activity by using phytohemagglutininin-stimulated peripheral blood mononuclear cell(PHA/PBM) test system1996Journal of medicinal chemistry, Apr-12, Volume: 39, Issue:8
Lipophilic, acid-stable, adenosine deaminase-activated anti-HIV prodrugs for central nervous system delivery. 3. 6-Amino prodrugs of 2'-beta-fluoro-2',3'-dideoxyinosine.
AID79148Percentage of gag protein expression using H9 cells at 100 uM on 12th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID79266Percentage of gag protein expression using H9 cells at 200 uM on 7th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID32053Anti-HIV activity (% toxicity) in ATH-8 cells at 5 uM in presence of 2'-deoxycoformycin at 20 uM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID26769Partition coefficient (logP)1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID104946Cytotoxicity was determined as the dose required to reduce the viability of uninfected MT-4 cells by 50%1987Journal of medicinal chemistry, Nov, Volume: 30, Issue:11
Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis.
AID46976Cytotoxic concentration in Wild Type CEM cells1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2'-fluoro-ara- and 2'-fluoro-ribo-2',3'- dideoxyadenosine as a strategy to bypass a metabolic blockade.
AID20354Kinetic parameter relative rate measured at 50 uM at pH 7.4 and 37 degree Centigrade1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.
AID79270Percentage of gag protein expression using H9 cells at 50 uM on 10th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
AID79150Percentage of gag protein expression using H9 cells at 20 uM on 10th day1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.70)18.7374
1990's16 (59.26)18.2507
2000's9 (33.33)29.6817
2010's1 (3.70)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: 12.33

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 Index12.33 (24.57)
Research Supply Index3.50 (2.92)
Research Growth Index5.82 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.33)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (6.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other30 (93.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		2106-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
9-(2-hydroxy-3-nonyl)adenine
9-(2-hydroxy-3-nonyl)adenine: specific inhibitor of adenosine deaminase		210
hydroxyurea
[no description available]		1.9810one-carbon compound;
ureas		antimetabolite;
antimitotic;
antineoplastic agent;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
genotoxin;
immunomodulator;
radical scavenger;
teratogenic agent
tyrosine
Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.		210amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
tyrosine		EC 1.3.1.43 (arogenate dehydrogenase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
stavudine
Stavudine: A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.. stavudine : A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase		3.7930dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
dideoxyadenosine
Dideoxyadenosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite.		9.52240adenosines;
purine 2',3'-dideoxyribonucleoside		EC 3.5.4.4 (adenosine deaminase) inhibitor;
EC 4.6.1.1 (adenylate cyclase) inhibitor
vidarabine
adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.		1.9910beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic
zalcitabine
Zalcitabine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.. zalcitabine : A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.		3.7830pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
fluorine
Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.		210diatomic fluorine;
gas molecular entity		NMR chemical shift reference compound
nitidine chloride
[no description available]		3.110
alovudine
[no description available]		1.9810pyrimidine 2',3'-dideoxyribonucleoside
azides
Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.		1.9910pseudohalide anionmitochondrial respiratory-chain inhibitor
nigericin
Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.		3.110polycyclic etherantibacterial agent;
antimicrobial agent;
bacterial metabolite;
potassium ionophore
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		4.3460azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
ribavirin
Rebetron: Rebetron is tradename		2.39201-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
lamivudine
[no description available]		3.110monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
kynostatin 272
kynostatin 272: structure given in first source; contains allophenylnorstatine as a transition-state mimic		3.110peptide
2',3'-dideoxycytidinene
2',3'-dideoxycytidinene: 2',3'-unsaturated derivative of 2',3'-dideoxycytidine; potent inhibitor of HTLV-III in vitro; structure given in first source		1.9810
calanolide a
calanolide A: NSC 661122 and costatolide are isomers; a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum (Clusiaceae); structure in first source. (+)-calanolide A : An organic heterotetracyclic compound that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one substituted by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10R,11S,12S stereoisomer). Isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase.		3.110cyclic ether;
delta-lactone;
organic heterotetracyclic compound;
secondary alcohol		HIV-1 reverse transcriptase inhibitor;
plant metabolite
2'3'-didehydro-2'3'-dideoxyadenosine
2'3'-didehydro-2'3'-dideoxyadenosine: structure given in first source		1.9710
1-(2,3-dideoxy-2-fluoropentofuranosyl)cytosine
[no description available]		1.9810
l 693593
L 693593: structure given in first source		1.9810
kynostatin 227
kynostatin 227: structure given in first source; contains allophenylnorstatine as a transition-state mimic		3.110
2',3'-dideoxyadenosine triphosphate
[no description available]		2.420purine deoxyribonucleoside triphosphate
zidovudine triphosphate
[no description available]		1.9910
2',3'-dideoxy-2',3'-didehydro-2'-fluorocytidine
2',3'-dideoxy-2',3'-didehydro-2'-fluorocytidine: has antiviral action against HIV-1; structure given in first source		1.9810
3'-deoxy-2',3'-didehydro-2'fluorothymidine
3'-deoxy-2',3'-didehydro-2'fluorothymidine: has antiviral activity against HIV-1; structure given in first source		1.9810
bosentan anhydrous
Bosentan: A sulfonamide and pyrimidine derivative that acts as a dual endothelin receptor antagonist used to manage PULMONARY HYPERTENSION and SYSTEMIC SCLEROSIS.		3.2110primary alcohol;
pyrimidines;
sulfonamide		antihypertensive agent;
endothelin receptor antagonist
pentostatin
Pentostatin: A potent inhibitor of ADENOSINE DEAMINASE. The drug induces APOPTOSIS of LYMPHOCYTES, and is used in the treatment of many lymphoproliferative malignancies, particularly HAIRY CELL LEUKEMIA. It is also synergistic with some other antineoplastic agents and has immunosuppressive activity.. pentostatin : A member of the class of coformycins that is coformycin in which the hydroxy group at position 2' is replaced with a hydrogen. It is a drug used for the treatment of hairy cell leukaemia.		1.9810coformycinsantimetabolite;
antineoplastic agent;
Aspergillus metabolite;
bacterial metabolite;
EC 3.5.4.4 (adenosine deaminase) inhibitor
3'-azido-2',3'-dideoxyadenosine
[no description available]		1.9710
12-deoxyphorbol 13-acetate
[no description available]		3.110phorbol estermetabolite
michellamine c
michellamine A: atropisomeric naphthylisoquinoline anti-HIV cytopathic alkaloid dimers; from tropical plant Ancistrocladus abbreviatus; structure given in first source. michellamine A : A dimeric isoquinoline alkaloid isolated from Ancistrocladus abbreviatus and has been shown to exhibit anti-HIV activity.		3.110
costatolide
(-)-calanolide B : An organic heterotetracyclic compound that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one substituted by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10S,11R,12S stereoisomer). Isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase.		3.110cyclic ether;
delta-lactone;
organic heterotetracyclic compound;
secondary alcohol		HIV-1 reverse transcriptase inhibitor;
plant metabolite
r-82913
R-82913: antiviral target on reverse transcriptase of HIV-1		1.9810
sitagliptin
sitagliptin : A triazolopyrazine that exhibits hypoglycemic activity.		3.2110triazolopyrazine;
trifluorobenzene		EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor;
environmental contaminant;
hypoglycemic agent;
serine proteinase inhibitor;
xenobiotic
fumarprotocetraric acid
fumarprotocetraric acid: RN given refers to (E)-isomer; structure given in first source		3.110carbonyl compound
guttiferone a
guttiferone A: antibacterial from Clusiaceae family; structure in first source		3.110
indinavir sulfate
Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.		3.2110dicarboxylic acid diamide;
N-(2-hydroxyethyl)piperazine;
piperazinecarboxamide		HIV protease inhibitor
pepstatin
pepstatin: inhibits the aspartic protease endothiapepsin		3.110pentapeptide;
secondary carboxamide		bacterial metabolite;
EC 3.4.23.* (aspartic endopeptidase) inhibitor
indigo carmine
3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.		3.110
ccx282-b
CCX282-B: antagonist of CCR9 chemokine receptor		3.2110
didanosine
Didanosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.. didanosine : A purine 2',3'-dideoxyribonucleoside that is inosine in which the hydroxy groups at both the 2' and the 3' positions on the sugar moiety have been replaced by hydrogen. An antiviral drug, it is used as a medication to treat HIV/AIDS.		4.88110purine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor;
geroprotector;
HIV-1 reverse transcriptase inhibitor
conocurvone
conocurvone: a trimeric naphthoquinone derivative; extracted from Conospermum incurvum; structure given in first source		3.110organic heterotricyclic compound;
organooxygen compound
2'-fluoro-2',3'-dideoxyinosine
2'-fluoro-2',3'-dideoxyinosine: structure given in first source; RN given refers to compound with unspecified F (fluorine) orientation		2.9140
ConditionIndicatedRelationship StrengthStudiesTrials
HIV
Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.		03.3670
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		01.9810
Viremia
The presence of viruses in the blood.		01.9810
HIV Coinfection
[description not available]		02.3920
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		02.3920
Acquired Immune Deficiency Syndrome
[description not available]		01.9910
AIDS Seroconversion
[description not available]		01.9910
Acquired Immunodeficiency Syndrome
An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.		01.9910
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		0210
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