Compounds > 2'3'-didehydro-2'3'-dideoxyadenosine
Page last updated: 2024-11-06

2'3'-didehydro-2'3'-dideoxyadenosine

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

Description

2'3'-didehydro-2'3'-dideoxyadenosine (ddA) is a nucleoside analog that has shown potent anti-HIV activity. It is a chain terminator of DNA synthesis and inhibits the replication of HIV-1 by acting as a substrate for the viral reverse transcriptase enzyme, preventing the conversion of viral RNA into DNA. ddA has been studied extensively for its potential as an antiviral agent and its mechanism of action. It was synthesized through a series of chemical reactions, including the deoxygenation and dehydration of adenosine. ddA is not currently used clinically due to its toxicity, but it has been important in understanding the mechanisms of antiviral drug action and in the development of other, more effective anti-HIV drugs.'

2'3'-didehydro-2'3'-dideoxyadenosine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID64975
CHEMBL ID290427
SCHEMBL ID112551
MeSH IDM0204360

Synonyms (29)

Synonym
2',3'-dideoxy-2'3'-didehydroadenosine
7057-48-9
adenosine, 2',3'-didehydro-2',3'-dideoxy-
[(2s,5r)-5-(6-aminopurin-9-yl)-2,5-dihydrofuran-2-yl]methanol
ddeado
2',3'-didehydro-2',3'-dideoxyadenosine
2',3'-dideoxy-2'-adenosinene
CHEMBL290427
AKOS004900469
beta-l-d4a
nsc 108602
unii-sk35877hi5
sk35877hi5 ,
2'3'-ddda
2'3'-didehydro-2'3'-dideoxyadenosine
2',3'-dideoxy-2',3'-didehydroadenosine
didanosine impurity i [ep impurity]
didanosine impurity i
didanosine impurity i [who-ip]
SCHEMBL112551
JFUOUIPRAAGUGF-NKWVEPMBSA-N
[(2s,5r)-5-(6-amino-9h-purin-9-yl)-2,5-dihydrofuran-2-yl]methanol
((2s,5r)-5-(6-amino-9h-purin-9-yl)-2,5-dihydrofuran-2-yl)methanol
CS-0018411
HY-100260
DTXSID70875924
AS-34578
Q27289250
A866596
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Deoxycytidine kinaseHomo sapiens (human)Km620.00000.40003.57908.5000AID55392
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
pyrimidine nucleotide metabolic processDeoxycytidine kinaseHomo sapiens (human)
CMP biosynthetic processDeoxycytidine kinaseHomo sapiens (human)
dAMP salvageDeoxycytidine kinaseHomo sapiens (human)
nucleoside phosphate biosynthetic processDeoxycytidine kinaseHomo sapiens (human)
adenosine catabolic processAdenosine deaminase Bos taurus (cattle)
cell adhesionAdenosine deaminase Bos taurus (cattle)
nucleotide metabolic processAdenosine deaminase Bos taurus (cattle)
purine ribonucleoside monophosphate biosynthetic processAdenosine deaminase Bos taurus (cattle)
inosine biosynthetic processAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
deoxyadenosine kinase activityDeoxycytidine kinaseHomo sapiens (human)
deoxycytidine kinase activityDeoxycytidine kinaseHomo sapiens (human)
deoxyguanosine kinase activityDeoxycytidine kinaseHomo sapiens (human)
ATP bindingDeoxycytidine kinaseHomo sapiens (human)
protein homodimerization activityDeoxycytidine kinaseHomo sapiens (human)
cytidine kinase activityDeoxycytidine kinaseHomo sapiens (human)
adenosine deaminase activityAdenosine deaminase Bos taurus (cattle)
protein bindingAdenosine deaminase Bos taurus (cattle)
zinc ion bindingAdenosine deaminase Bos taurus (cattle)
2'-deoxyadenosine deaminase activityAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
nucleoplasmDeoxycytidine kinaseHomo sapiens (human)
cytosolDeoxycytidine kinaseHomo sapiens (human)
mitochondrionDeoxycytidine kinaseHomo sapiens (human)
cytoplasmDeoxycytidine kinaseHomo sapiens (human)
lysosomeAdenosine deaminase Bos taurus (cattle)
cytoplasmic vesicle lumenAdenosine deaminase Bos taurus (cattle)
anchoring junctionAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (47)

Assay IDTitleYearJournalArticle
AID23359Hydrolysis half life in glycine/HCl buffer at the specified pH of 1.51999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID105753Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 125 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID25128Half life of the compound1997Journal of medicinal chemistry, Nov-21, Volume: 40, Issue:24
Enzymatic properties of the unnatural beta-L-enantiomers of 2',3'-dideoxyadenosine and 2',3'-didehydro-2',3'-dideoxyadenosine.
AID33983Inhibitory activity against bovine liver adenosine Kinase; NS, NI/Ino=nonsubstrate, noninhibitor/inhibitor1997Journal of medicinal chemistry, Nov-21, Volume: 40, Issue:24
Enzymatic properties of the unnatural beta-L-enantiomers of 2',3'-dideoxyadenosine and 2',3'-didehydro-2',3'-dideoxyadenosine.
AID47113In vitro inhibition of HIV-2 replication in human T-lymphocytic cells (CEM).1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
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.
AID1068979Antiviral activity against HIV-2 ROD infected in human MT4 cells2014Bioorganic & medicinal chemistry letters, Feb-01, Volume: 24, Issue:3
Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents.
AID33650Kcat/KM of compound against adenosine deaminase (ADA) was determined; Not available2004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.
AID46975In vitro cytotoxic concentration in CEM cells.1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID1068976Cytotoxicity against human CEM/0 cells2014Bioorganic & medicinal chemistry letters, Feb-01, Volume: 24, Issue:3
Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents.
AID235291Compound was evaluated for its ability to inhibit the growth of HIV-2 in CEM cell culture (CC50/EC50)1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID19628Partition coefficient (logP)1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID32065Protection of ATH8 cells against the cytopathic effect of HIV.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID105750Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID43987Effect 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',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID1068975Antiviral activity against HIV-2 ROD infected in thymidine kinase-deficient human CEM cells2014Bioorganic & medicinal chemistry letters, Feb-01, Volume: 24, Issue:3
Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents.
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.
AID33647Kcat value against adenosine deaminase (ADA); Not available2004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.
AID47111In vitro inhibition of HIV-1 replication in human T-lymphocytic cells (CEM).1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID1068978Cytotoxicity against human MT4 cells2014Bioorganic & medicinal chemistry letters, Feb-01, Volume: 24, Issue:3
Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents.
AID33645Menten constant against adenosine deaminase (ADA)2004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.
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.
AID26764Compound was evaluated for its lipophilicity by 1-octanol/water (phosphate buffer, pH 7.0) and the partition coefficient (log P) was reported.1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID55392Inhibitory activity against human deoxycytidine kinase1997Journal of medicinal chemistry, Nov-21, Volume: 40, Issue:24
Enzymatic properties of the unnatural beta-L-enantiomers of 2',3'-dideoxyadenosine and 2',3'-didehydro-2',3'-dideoxyadenosine.
AID46966Compound was evaluated for its concentration (potency) to inhibit the growth of CEM cells.1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID44134Minimal 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',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID23365Hydrolysis half life in phosphate buffer at the specified pH of 7.3; Not available1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID11772Compound was evaluated for esterase half-life (t 1/2) period using Pig Liver Esterase (PLE) assay; ND is not determined1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID234204Therapeutic index (Ratio = ID50/ED50).1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID1068977Antiviral activity against HIV-2 ROD infected in human CEM/0 cells2014Bioorganic & medicinal chemistry letters, Feb-01, Volume: 24, Issue:3
Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents.
AID8121Ability to get deaminated by adenosine deaminase (ADA); Expressed as t1/22004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.
AID47128Compound was evaluated for its effective concentration (potency) to inhibit the growth of HIV-1 in CEM cell culture.1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID1068980Antiviral activity against HIV-1 3B infected in human MT4 cells2014Bioorganic & medicinal chemistry letters, Feb-01, Volume: 24, Issue:3
Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents.
AID235290Compound was evaluated for its ability to inhibit the growth of HIV-1 in CEM cell culture (CC50/EC50)1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID105764Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 125 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID105762Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID47129Compound was evaluated for its effective concentration (potency) to inhibit the growth of HIV-2 in CEM cell culture.1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID105759Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.00032 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID33640Inhibitory activity against bovine adenosine deaminase; very weak substrate or inhibitor1997Journal of medicinal chemistry, Nov-21, Volume: 40, Issue:24
Enzymatic properties of the unnatural beta-L-enantiomers of 2',3'-dideoxyadenosine and 2',3'-didehydro-2',3'-dideoxyadenosine.
AID105756Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 5 uM concentration.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID105760Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.008 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID28386Partition coefficient in 1-octanol and 10 mM aqueous potassium phosphate buffer at pH 7.41989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Nucleic acid related compounds. 57. Synthesis, x-ray crystal structure, lipophilic partition properties, and antiretroviral activities of anomeric 3'-azido-2',3'-dideoxy-2,6-diaminopurine ribosides.
AID235638Selectivity 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',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID105766Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 5 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID164942Inhibitory activity against purine nucleoside phosphorylases from human blood and calf spleen; NS, NI/Ino=nonsubstrate, noninhibitor/inhibitor1997Journal of medicinal chemistry, Nov-21, Volume: 40, Issue:24
Enzymatic properties of the unnatural beta-L-enantiomers of 2',3'-dideoxyadenosine and 2',3'-didehydro-2',3'-dideoxyadenosine.
AID32066Required dose to reduce viability of normal uninfected ATH8 cells.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID23360Hydrolysis half life in glycine/HCl buffer at the specified pH of 3.01999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (15.00)18.7374
1990's5 (25.00)18.2507
2000's10 (50.00)29.6817
2010's2 (10.00)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: 11.49

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 Index11.49 (24.57)
Research Supply Index3.09 (2.92)
Research Growth Index4.58 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.49)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
thymidine
[no description available]		1.9710pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		1.9910alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
adenosine monophosphate
Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.		1.9910adenosine 5'-phosphate;
purine ribonucleoside 5'-monophosphate		adenosine A1 receptor agonist;
cofactor;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
EC 3.1.3.11 (fructose-bisphosphatase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
thiazoles
[no description available]		2.04101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
2-aminopurine
2-Aminopurine: A purine that is an isomer of ADENINE (6-aminopurine).. aminopurine : Any purine having at least one amino substituent.. 2-aminopurine : The parent compound of the 2-aminopurines, comprising a purine core carrying an amino substituent at the 2-position.		2.04102-aminopurines;
nucleobase analogue		antimetabolite
deoxycytidine
[no description available]		1.9710pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
2'-deoxyadenosine
2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source		2.3720purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
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		2.6930dihydrofuran;
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.		4.25180adenosines;
purine 2',3'-dideoxyribonucleoside		EC 3.5.4.4 (adenosine deaminase) inhibitor;
EC 4.6.1.1 (adenylate cyclase) inhibitor
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.		2.4120pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
alovudine
[no description available]		1.9710pyrimidine 2',3'-dideoxyribonucleoside
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.		3.0950azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
lamivudine
[no description available]		2.4320monothioacetal;
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
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		2.4220adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
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		2.3920
thiazolyl blue
thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.		2.0410organic bromide saltcolorimetric reagent;
dye
2,6-diaminopurine 2',3'-dideoxyriboside
2,6-diaminopurine 2',3'-dideoxyriboside: selectively inhibits HIV virus replication in vitro; structure given in first source		1.9710
3'-azido-2',3'-dideoxy-5-methylcytidine
3'-azido-2',3'-dideoxy-5-methylcytidine: inhibits reproduction of AIDS virus in cultured cells		1.9710
2',3'-dideoxythymidine
[no description available]		1.9710
2',3'-didehydro-2',3'-dideoxyuridine
[no description available]		1.9710
2',5'-dideoxyadenosine
[no description available]		1.9910deoxyribonucleoside
aristeromycin
aristeromycin: RN given refers to (1R-(1alpha,2alpha,3beta,5alpha)-isomer		210
lodenosine
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		1.9710
3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside
3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside: structure given in first source		1.9710
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		2.0210
3'-azido-2',3'-dideoxyadenosine
[no description available]		2.6630
adenosine kinase
Adenosine Kinase: An enzyme that catalyzes the formation of ADP plus AMP from adenosine plus ATP. It can serve as a salvage mechanism for returning adenosine to nucleic acids. EC 2.7.1.20.		1.9910
deoxyguanosine
[no description available]		1.9710purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
nsc 614846
carbovir: structure given in first source; potent & selective anti-HIV agent. carbovir : Cyclopent-2-en-1-ylmethanol in which the 4-position is substituted by a 2-amino-6-hydroxy-9H-purin-9-yl group such that the two substitutents on the cyclopentene ring are in a cis relationship. The (-)-enantiomer, also known as carbovir, is a potent inhibitor of HIV replication replication in cell cultures.. (-)-carbovir : The (active) (-)-enantiomer of the carbocyclic analogue of 2',3'-dideoxy-2',3'-didehydroguanosine.		2.110carbovirHIV-1 reverse transcriptase inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Cell Transformation, Viral
An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.		02.3920
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.		02.8940
Cancer of Liver
[description not available]		02.4220
Liver Neoplasms
Tumors or cancer of the LIVER.		02.4220
Hepatitis B Virus Infection
[description not available]		02.4420
Hepatitis B
INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.		02.4420