Compounds > 2',3'-dideoxyadenosine 5'-phosphate
Page last updated: 2024-12-06

2',3'-dideoxyadenosine 5'-phosphate

2',3'-dideoxyadenosine 5'-phosphate, also known as ddA, is a synthetic nucleoside analog that acts as a chain terminator during DNA synthesis. It is structurally similar to deoxyadenosine, but lacks the 2' and 3' hydroxyl groups on the ribose sugar. This modification prevents the addition of further nucleotides to the growing DNA chain. ddA is an important component of some antiviral therapies, including the treatment of HIV infection. The absence of the 2' and 3' hydroxyl groups prevents the formation of the phosphodiester bond required for chain elongation. This makes ddA a potent inhibitor of DNA polymerase, which is the enzyme responsible for replicating DNA. The ability of ddA to block DNA synthesis has led to its use as a therapeutic agent against various viruses, including HIV. ddA is typically administered in combination with other antiviral agents. The study of ddA is essential for understanding the mechanisms of viral replication and for developing new antiviral therapies. Research into ddA has provided valuable insights into the structure and function of DNA polymerase, and has led to the development of other potent antiviral drugs.'

Cross-References

ID SourceID
PubMed CID65356
CHEMBL ID1162296
SCHEMBL ID285262
MeSH IDM0055382

Synonyms (21)

Synonym
ddamp
nsc615566
107132-15-0
[(2s,5r)-5-(6-aminopurin-9-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
2',3-dideoxyadenosine 5'-monophosphate
[(2s,5r)-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate
CHEMBL1162296 ,
2',3'-dideoxyadenosine 5'-phosphate
26315-32-2
2',3'-dideoxyadenosine monophosphate
5'-adenylic acid, 2',3'-dideoxy-
SCHEMBL285262
bdbm50478976
2',3'-dideoxyadenosine 5'-monophosphate
2DA ,
2',3'-dideoxyadenosine-5'-monophosphate
[(2s,5r)-5-(6-amino-9h-purin-9-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
Q27452910
((2s,5r)-5-(6-amino-9h-purin-9-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate
[5-(6-amino-9h-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate
DTXSID60910237
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Kd0.10000.00062.40599.8000AID341978
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Activity0.25000.00091.30738.0000AID341977; AID341992
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID341992Inhibition of HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant assessed as dCTP level required to form 80% of binary enzyme complex formation with drug-terminated primer in posttranslocation state by site-specific foot printing assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID341978Binding affinity to ternary complex of HIV1 reverse transcriptase with primer/template in presence of dCTP substrate2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID341977Inhibition of HIV1 reverse transcriptase assessed as dCTP level required to form 80% of binary enzyme complex formation with drug-terminated primer in posttranslocation state by site-specific foot printing assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID341976Inhibition of HIV1 reverse transcriptase assessed as dCTP level required to form 50% of binary enzyme complex formation with drug-terminated primer in posttranslocation state by site-specific foot printing assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID341991Inhibition of HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant assessed as dCTP level required to form 50% of binary enzyme complex formation with drug-terminated primer in posttranslocation state by site-specific foot printing assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID1865852Prodrug conversion in inactivated fetal calf serum with RPMI 1640 culture medium assessed as parent ddA formation at 0.00005 M measured at 50 to 150 hrs by HPLC analysis
AID1865859Prodrug conversion in human CEM-SS cell extract assessed as parent ddA formation at 0.00005 M measured at 50 to 150 hrs by HPLC analysis
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (7.69)18.7374
1990's6 (46.15)18.2507
2000's5 (38.46)29.6817
2010's0 (0.00)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.25

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 Index12.25 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index5.03 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.25)

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%
Other15 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		1.95106-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		1.9510
foscarnet
Foscarnet: An antiviral agent used in the treatment of cytomegalovirus retinitis. Foscarnet also shows activity against human herpesviruses and HIV.. phosphonoformic acid : Phosphoric acid in which one of the hydroxy groups is replaced by a carboxylic acid group. It is used as the trisodium salt as an antiviral agent in the treatment of cytomegalovirus retinitis (CMV retinitis, an inflamation of the retina that can lead to blindness) and as an alternative to ganciclovir for AIDS patients who require concurrent antiretroviral therapy but are unable to tolerate ganciclovir due to haematological toxicity.		2.0110carboxylic acid;
one-carbon compound;
phosphonic acids		antiviral drug;
geroprotector;
HIV-1 reverse transcriptase inhibitor;
sodium-dependent Pi-transporter inhibitor
thymidine
[no description available]		1.9510pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
uridine
[no description available]		1.9510uridinesdrug metabolite;
fundamental metabolite;
human metabolite
adenosine monophosphate
Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.		210adenosine 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
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.		1.99102-aminopurines;
nucleobase analogue		antimetabolite
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.		1.9810adenosines;
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.		1.9510beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic
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.		2.730azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		2.3720adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
thymidine 5'-triphosphate
thymidine 5'-triphosphate: RN given refers to parent cpd. dTTP : A thymidine phosphate having a triphosphate group at the 5'-position.		1.9910pyrimidine 2'-deoxyribonucleoside 5'-triphosphate;
thymidine phosphate		Escherichia coli metabolite;
mouse metabolite
2',3'-dideoxyadenosine triphosphate
[no description available]		2.9140purine deoxyribonucleoside triphosphate
3'-azido-3'-deoxythymidine 5'phosphate
3'-azido-3'-deoxythymidine 5'phosphate: inhibits thymidylate kinase		2.7130
zidovudine triphosphate
[no description available]		2.0310
tenofovir
tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.		2.0310nucleoside analogue;
phosphonic acids		antiviral drug;
drug metabolite;
HIV-1 reverse transcriptase inhibitor
pyrophosphate
Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.		2.4220diphosphate ion
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.		2.6830purine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor;
geroprotector;
HIV-1 reverse transcriptase inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
HIV Coinfection
[description not available]		02.0210
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).		02.0210
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.		02.3820
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.		0210
Carcinoma, Ehrlich Tumor
A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.		01.9510
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