5-amino-2'-deoxyuridine is a synthetic nucleoside analog that has shown significant antitumor activity. It is a potent inhibitor of thymidylate synthase, an enzyme essential for DNA synthesis. This inhibition leads to the depletion of thymidine triphosphate (dTTP), a building block of DNA, and ultimately results in DNA replication arrest and cell death. Research has focused on its potential as a therapeutic agent for various cancers, particularly those with high thymidylate synthase expression. Furthermore, 5-amino-2'-deoxyuridine has been explored for its antiviral properties, particularly against Herpes simplex virus (HSV) and cytomegalovirus (CMV). Studies have shown that it can inhibit viral DNA replication, potentially contributing to antiviral effects.'
5-amino-2'-deoxyuridine: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 111081 |
| CHEMBL ID | 3143491 |
| SCHEMBL ID | 345268 |
| MeSH ID | M0365753 |
| Synonym |
|---|
| 5-amino-2'-deoxyuridine |
| 5536-30-1 |
| 5-amino-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione |
| 5-amino-durd |
| 5-amino-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1h-pyrimidine-2,4-dione |
| chembl3143491 , |
| bdbm50000966 |
| 5-amino-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione |
| 5-amino-du |
| einecs 226-894-4 |
| SCHEMBL345268 |
| 5-amino-1-((2s,4r,5s)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione;5-amino-durd; ag-f-93470; surecn345268; ac1l38yh; ac1q69hm |
| 5-aminodeoxyuridine |
| 5-amino-deoxyuridine |
| OZMVAFPILSPXRM-RRKCRQDMSA-N |
| DTXSID10203909 |
| 5-amino-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione |
| A848620 |
| EN300-19734321 |
| 5-amino-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Thymidine kinase, cytosolic | Rattus norvegicus (Norway rat) | Ki | 370.0000 | 2.4000 | 4.2000 | 6.5000 | AID210886 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID210888 | Affinity towards cytoplasmic Thymidine kinase relative ot TdR. | 1982 | Journal 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. |
| AID126594 | Competitive inhibition against rat mitochondrial thymidine kinase | 1982 | Journal 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. |
| AID126600 | Affinity towards mitochondrial thymidine kinase relative to TdR. | 1982 | Journal 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. |
| AID1136938 | Non-competitive inhibition of Escherichia coli B thymidine kinase using [2-14C]-thymidine as substrate assessed as formation of [14C]-TMP after 10 mins by Lineweaver-Burk double reciprocal plot analysis | 1979 | Journal of medicinal chemistry, Dec, Volume: 22, Issue:12 | Design of species- or isozyme-specific enzyme inhibitors. 2. Differences between a bacterial and a mammalian thymidine kinase in the effect of thymidine substituents on affinity for the thymidine site. |
| AID233146 | Differential affinity is the ratio between M-TK and C-TK | 1982 | Journal 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. |
| AID210886 | Competitive inhibition against rat cytoplasmic Thymidine kinase | 1982 | Journal 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. |
| AID1124544 | Competitive inhibition of thymidine kinase in BHK21 (C13) cells using thymidine as substrate assessed as formation of TMP by Lineweaver-Burk plot analysis | 1979 | Journal of medicinal chemistry, Jun, Volume: 22, Issue:6 | Design of species- or isozyme-specific enzyme inhibitors. 1. Effect of thymidine substituents on affinity for the thymidine site of hamster cytoplasmic thymidine kinase. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 3 (60.00) | 18.7374 |
| 1990's | 1 (20.00) | 18.2507 |
| 2000's | 1 (20.00) | 29.6817 |
| 2010's | 0 (0.00) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (12.42) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 5 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||