Page last updated: 2024-09-23

2',3'-dideoxythymidine

Cross-References

ID SourceID
PubMed CID65119
CHEMBL ID444314
SCHEMBL ID23485
MeSH IDM0071724

Synonyms (40)

Synonym
thymidine, 3'-deoxy-
2',3'-dideoxythymidine & granulocyte-macrophage colony-stimulating factor
ddt & gm-csf
1-[(2r,5s)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione
thymidine, 3'-deoxy- & colony-stimulating factor 2
d2t ,
3'-deoxythymidine ,
nsc617596
3416-05-5
thymidine, 2',3'-dideoxy-
3'-deoxythymidine, 98%
dideoxythymidine
CHEMBL444314 ,
1-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
2',3'-dideoxythymidine
1-((2r,5s)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione
1-(5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione
bdbm50018445
cid_5280
1-((2r,5s)-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione
nsc 617596
AKOS015999118
AKOS015912435
SCHEMBL23485
1-[(2r,5s)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1h,3h)-dione
38S ,
XKKCQTLDIPIRQD-JGVFFNPUSA-N
W-200577
AC-32184
mfcd00010570
DTXSID60187760
desoxythymidin
3'-deoxy thymidine
DS-14580
Q27453630
CS-W013027
A852119
1-((2r,5s)-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione;1-((2r,5s)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione
PD150966
Z2044774928

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine kinase, cytosolic Rattus norvegicus (Norway rat)Ki400.00002.40004.20006.5000AID210886
Reverse transcriptase/RNaseH Human immunodeficiency virus 1IC50 (µMol)0.08500.00011.076810.0000AID197924; AID289142
[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)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
DNA damage responseThymidine phosphorylaseEscherichia coli K-12
pyrimidine nucleobase metabolic processThymidine phosphorylaseEscherichia coli K-12
pyrimidine nucleoside metabolic processThymidine phosphorylaseEscherichia coli K-12
thymidine metabolic processThymidine phosphorylaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
1,4-alpha-oligoglucan phosphorylase activityThymidine phosphorylaseEscherichia coli K-12
thymidine phosphorylase activityThymidine phosphorylaseEscherichia coli K-12
glycosyltransferase activityThymidine phosphorylaseEscherichia coli K-12
pentosyltransferase activityThymidine phosphorylaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
cytosolThymidine phosphorylaseEscherichia coli K-12
membraneThymidine phosphorylaseEscherichia coli K-12
cytosolThymidine phosphorylaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (59)

Assay IDTitleYearJournalArticle
AID230271Ratio of TICD50 to that of IC50 of human immunodeficiency virus (HIV-1)1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID458192Activity at Drosophila melanogaster dNK by spectrophotometry2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
Synthesis of fluorescent nucleoside analogs as probes for 2'-deoxyribonucleoside kinases.
AID163315Concentration of compound required to inhibit 50% of viral replication of Rauscher-Murine leukemia virus1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia
AID197924Concentration required to inhibit HIV reverse transcriptase1992Journal of medicinal chemistry, Sep-04, Volume: 35, Issue:18
3',3'-Difluoro-3'-deoxythymidine: comparison of anti-HIV activity to 3'-fluoro-3'-deoxythymidine.
AID230269Ratio of TICD50 to that of IC50 of Rauscher-Murine leukemia virus (R-MuLv)1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia
AID1865837Anti-HIV activity against HIV-1 infected in human CEM-TK(-) cells assessed as inhibition of viral replication
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
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.
AID1865836Anti-HIV activity against HIV-1 infected in human CEM-SS cells assessed as inhibition of viral replication
AID126594Competitive inhibition against rat mitochondrial thymidine kinase1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Species- or isozyme-specific enzyme inhibitors. 5. Differential effects of thymidine substituents on affinity for rat thymidine kinase isozymes.
AID381860Activity of Escherichia coli thymidine phosphorylase assessed as drug phosphorylation after 1 hr2008Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7
Kinetic parameters and recognition of thymidine analogues with varying functional groups by thymidine phosphorylase.
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.
AID381859Activity of Escherichia coli thymidine phosphorylase2008Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7
Kinetic parameters and recognition of thymidine analogues with varying functional groups by thymidine phosphorylase.
AID126600Affinity towards mitochondrial thymidine kinase relative to TdR.1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Species- or isozyme-specific enzyme inhibitors. 5. Differential effects of thymidine substituents on affinity for rat thymidine kinase isozymes.
AID289141Inhibition of virus-induced cytopathic effect in wild type HIV 3a infected MT2 cells after 5 days2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Synthesis, anti-HIV activity, and resistance profile of thymidine phosphonomethoxy nucleosides and their bis-isopropyloxymethylcarbonyl (bisPOC) prodrugs.
AID125177In vitro inhibitory activity against Moloney murine leukemia virus (M-MULV) replication, a mammalian T-lymphotropic retrovirus1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Synthesis and antiviral activity of various 3'-azido, 3'-amino, 2',3'-unsaturated, and 2',3'-dideoxy analogues of pyrimidine deoxyribonucleosides against retroviruses.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1865843Cytotoxicity against human MT4 cells assessed as reduction in cell viability
AID125179Compound was tested against Moloney murine leukemia virus (M-MULV) in 3T3 cells, at a concentration of 100 uM1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Synthesis and antiviral activity of various 3'-azido, 3'-amino, 2',3'-unsaturated, and 2',3'-dideoxy analogues of pyrimidine deoxyribonucleosides against retroviruses.
AID105747Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.008 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.
AID105373Concentration required to reduce the number of viable cells in the untreated MT-4 cell culture1992Journal of medicinal chemistry, Sep-04, Volume: 35, Issue:18
3',3'-Difluoro-3'-deoxythymidine: comparison of anti-HIV activity to 3'-fluoro-3'-deoxythymidine.
AID105578Concentration required to affect a 50% reduction in the cytopathic effect of HIV for MT-4 cells1992Journal of medicinal chemistry, Sep-04, Volume: 35, Issue:18
3',3'-Difluoro-3'-deoxythymidine: comparison of anti-HIV activity to 3'-fluoro-3'-deoxythymidine.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID152642Cytotoxic effect in uninfected human peripheral blood mononuclear (PBM) cells1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral blood mononuclear cells.
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.
AID233146Differential affinity is the ratio between M-TK and C-TK1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Species- or isozyme-specific enzyme inhibitors. 5. Differential effects of thymidine substituents on affinity for rat thymidine kinase isozymes.
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
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.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1865842Cytotoxicity against human CEM-TK(-) cells assessed as reduction in cell viability
AID1865838Anti-HIV activity against HIV-1 infected in human MT4 cells assessed as inhibition of viral replication
AID289142Inhibition of HIV1 reverse transcriptase2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Synthesis, anti-HIV activity, and resistance profile of thymidine phosphonomethoxy nucleosides and their bis-isopropyloxymethylcarbonyl (bisPOC) prodrugs.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID125178Compound was tested against Moloney murine leukemia virus (M-MULV) in 3T3 cells, at a concentration of 10 uM1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Synthesis and antiviral activity of various 3'-azido, 3'-amino, 2',3'-unsaturated, and 2',3'-dideoxy analogues of pyrimidine deoxyribonucleosides against retroviruses.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1865841Cytotoxicity against human CEM-SS cells assessed as reduction in cell viability
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.
AID45017Concentration of compound required to inhibit 50% of host cell replication of human immunodeficiency virus in CEM-F cells1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia
AID45016Concentration of compound required to inhibit 50% of viral replication of human immunodeficiency virus in CEM-F cells1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia
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.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID381854Activity of Escherichia coli thymidine phosphorylase assessed as drug phosphorylation after 2 hrs2008Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7
Kinetic parameters and recognition of thymidine analogues with varying functional groups by thymidine phosphorylase.
AID105751Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 uM concentration; Range is 10-401987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID154959Antiviral activity against HIV I strain (LAV) in human peripheral blood mononuclear (PBM) cells1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral blood mononuclear cells.
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID210888Affinity towards cytoplasmic Thymidine kinase relative ot TdR.1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Species- or isozyme-specific enzyme inhibitors. 5. Differential effects of thymidine substituents on affinity for rat thymidine kinase isozymes.
AID210886Competitive inhibition against rat cytoplasmic Thymidine kinase1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Species- or isozyme-specific enzyme inhibitors. 5. Differential effects of thymidine substituents on affinity for rat thymidine kinase isozymes.
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.
AID163316Concentration of compound required to inhibit 50% of host cell replication of Rauscher-Murine leukemia virus1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (53)

TimeframeStudies, This Drug (%)All Drugs %
pre-199032 (60.38)18.7374
1990's14 (26.42)18.2507
2000's4 (7.55)29.6817
2010's2 (3.77)24.3611
2020's1 (1.89)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 (%)
Trials0 (0.00%)5.53%
Reviews1 (1.85%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other53 (98.15%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (1)

ArticleYear
The effect of DNA polymerase inhibitors on the cytotoxicity of cisplatin in human ovarian carcinoma cells.
Cancer communications, Volume: 2, Issue: 4
1990
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Interactions (1)

ArticleYear
Synergistic inhibition of human immunodeficiency virus type 1 replication in vitro by two-drug and three-drug combinations of 3'-azido-3'-deoxythymidine, phosphonoformate, and 2',3'-dideoxythymidine.
Antimicrobial agents and chemotherapy, Volume: 35, Issue: 10
1991
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]