Page last updated: 2024-12-07
3'-amino-2',3'-dideoxyuridine
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
3'-amino-2',3'-dideoxyuridine (3'-NH2-ddU) is a nucleoside analog that has shown promising antiviral activity against a variety of viruses, including HIV, hepatitis B, and herpes simplex virus. Its synthesis typically involves the modification of uridine, where the 2' and 3' hydroxyl groups are replaced with hydrogen atoms, and an amino group is introduced at the 3' position. 3'-NH2-ddU acts as a chain terminator during DNA replication by inhibiting the activity of DNA polymerases. This inhibition occurs due to the lack of a 3' hydroxyl group, which is essential for the formation of phosphodiester bonds between nucleotides. 3'-NH2-ddU has been extensively studied for its potential therapeutic applications in treating viral infections. Its antiviral activity, mechanism of action, and potential side effects have been investigated in numerous preclinical and clinical studies.'
3'-amino-2',3'-dideoxyuridine: structure given in first source; a major metabolite of the antiviral agent, 3'-azido-2',3'-dideoxyuridine [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 122107 |
| CHEMBL ID | 2021391 |
| MeSH ID | M0206368 |
Synonyms (12)
| Synonym |
|---|
| 3'-nh2-ddu |
| 3'-amino-2',3'-dideoxyuridine |
| 84472-86-6 |
| uridine, 3'-amino-2',3'-dideoxy- |
| 1-[(2r,4s,5s)-4-amino-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione |
| amddu |
| 1-[(2r,4s,5s)-4-amino-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione |
| CHEMBL2021391 |
| DTXSID50233442 |
| mfcd00872044 |
| A855651 |
| 1-[(2r,4s,5s)-4-amino-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione |
Research Excerpts
Dosage Studied
| Excerpt | Relevance | Reference |
|---|---|---|
| " At an optimum dosage level of 40 mg/kg, 7 and 8 produced 90% and 60% "cures" (greater than 60-day survivors), respectively." | ( Antineoplastic activity of 3'-(chloroethyl)nitrosourea analogues of 2'-deoxyuridine and 2'-deoxy-5-fluorouridine. Brubaker, WF; Lin, TS; Park, S; Prusoff, WH; Wang, ZH, 1986) | 0.27 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Bioassays (26)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID155775 | Minimum inhibitory concentration against Pasteurella multocida | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID50534 | Minimum inhibitory concentration against Citrobacter freundii | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID98046 | In vitro inhibition against replication of L1210 murine cells | 1983 | Journal of medicinal chemistry, Dec, Volume: 26, Issue:12 | Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides. |
| AID163407 | Minimum inhibitory concentration against Proteus vulgaris | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID201396 | Minimum inhibitory concentration against Salmonella typhi | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID55275 | In vitro cytotoxicity against human D-38 cells. | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID162881 | Minimum inhibitory concentration against Proteus mirabilis | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID152642 | Cytotoxic effect in uninfected human peripheral blood mononuclear (PBM) cells | 1989 | Journal 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. |
| AID210869 | Inhibitory activity against thymidine kinase (TK) from L1210 cells | 1983 | Journal of medicinal chemistry, Dec, Volume: 26, Issue:12 | Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides. |
| AID94565 | in vitro cytotoxicity against mouse L cells. | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID69202 | Minimum inhibitory concentration against Escherichia coli | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID56582 | Inhibitory activity against deoxycytidine kinase from L1210 cells | 1983 | Journal of medicinal chemistry, Dec, Volume: 26, Issue:12 | Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides. |
| AID98520 | Ability to effect the replication of L1210 cells in vitro | 1983 | Journal of medicinal chemistry, Apr, Volume: 26, Issue:4 | Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogues of pyrimidine deoxyribonucleoside. |
| AID97975 | Compound was tested in vitro for cytotoxicity against L1210 leukemia cells in tumor bearing mice. | 1986 | Journal of medicinal chemistry, May, Volume: 29, Issue:5 | Antineoplastic activity of 3'-(chloroethyl)nitrosourea analogues of 2'-deoxyuridine and 2'-deoxy-5-fluorouridine. |
| AID200872 | Minimum inhibitory concentration against Salmonella Typhimurium | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID201885 | In vitro inhibition against replication of Sarcoma-80 cells | 1983 | Journal of medicinal chemistry, Dec, Volume: 26, Issue:12 | Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides. |
| AID67853 | Minimum inhibitory concentration against Enterobacter aerogenes | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID199112 | Ability to effect the replication of S-180 cells in vitro | 1983 | Journal of medicinal chemistry, Apr, Volume: 26, Issue:4 | Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogues of pyrimidine deoxyribonucleoside. |
| AID93874 | Minimum inhibitory concentration against Klebsiella pneumoniae | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID216569 | Minimum inhibitory concentration against Vibrio cholerae | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID154959 | Antiviral activity against HIV I strain (LAV) in human peripheral blood mononuclear (PBM) cells | 1989 | Journal 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. |
| AID207203 | In vitro minimum inhibitory concentration against Staphylococcus aureus | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID31821 | In vitro antiviral activity against adeno virus using plaque reduction assay. | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID162934 | Minimum inhibitory concentration against Pseudomonas aeruginosa | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID203153 | Minimum inhibitory concentration against Serratia marcescens | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| AID203189 | Minimum inhibitory concentration against Shigella flexneri | 1983 | Journal of medicinal chemistry, Jun, Volume: 26, Issue:6 | 3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (6)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 5 (83.33) | 18.7374 |
| 1990's | 1 (16.67) | 18.2507 |
| 2000's | 0 (0.00) | 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] | ||
Market Indicators
Research Demand Index: 12.35
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 (12.35) All Compounds (24.57) |
Study Types
| 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 | 6 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||