Compounds > 5'-amino-2',5'-dideoxythymidine
Page last updated: 2024-09-23

5'-amino-2',5'-dideoxythymidine

Description

5'-amino-5'-deoxythymidine: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65311
CHEMBL ID319447
SCHEMBL ID51992
MeSH IDM0082006

Synonyms (26)

Synonym
5'-amino-5'-deoxythymidine
25152-20-9
adthd
1-[(2r,4s,5r)-5-(aminomethyl)-4-hydroxy-tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione
5'-amino-5-deoxythymidine
5'-amino-5-methyl-2',5'-dideoxyuridine
1-((2r,4s,5s)-5-aminomethyl-tetrahydro-furan-2-yl)-5-methyl-2,4(1h,3h)-pyrimidinedione
5'-nh2-5-ch3-ddu
5'-nh2-2'-dt
1-((2r,4s,5r)-5-(aminomethyl)-4-hydroxy-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione
1-((2r,5r)-5-aminomethyl-4-hydroxy-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione
5''-amino-5''-deoxythymidine
bdbm50132297
1-[(2r,4s,5r)-5-(aminomethyl)-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
CHEMBL319447 ,
5-addot
5'-amino-2',5'-dideoxythymidine
nsc 169339
SCHEMBL51992
PYWLBQPICCQJFF-XLPZGREQSA-N
5??-amino-5??-deoxythymidine
AKOS030530880
DTXSID30876098
1-((2r,4s,5r)-5-(aminomethyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione
Q27455601
5'-amino-5'-deoxy-d-thymidine

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine kinase, cytosolic Rattus norvegicus (Norway rat)Ki2.40002.40004.20006.5000AID210886
Thymidylate kinaseMycobacterium tuberculosis H37RvKi12.00004.50008.500010.0000AID210904
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (22)

Assay IDTitleYearJournalArticle
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.
AID1131500Antiviral activity against HSV1 at 400 uM1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
Synthesis and biological activity of several amino analogues of thymidine.
AID1131501Antineoplastic activity against mouse S180 cells at 400 uM1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
Synthesis and biological activity of several amino analogues of thymidine.
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.
AID210877The compound was tested for inhibition of thymidine kinase using [3H]TMP as radioligand at concentration 50 uM in L1210 cells1984Journal of medicinal chemistry, Aug, Volume: 27, Issue:8
A reappraisal of the effect upon thymidine kinase of thymidine derivatives carrying large groups at the 5'-position.
AID1145766Cytotoxicity against African green monkey Vero cells assessed as inhibition of replication1976Journal of medicinal chemistry, Apr, Volume: 19, Issue:4
Synthesis and antiviral activity of 5- and 5'-substituted thymidine analogs.
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.
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.
AID1136939Competitive 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 analysis1979Journal 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.
AID210871Thymidine kinase activity was measured by nonradiochemical assay method - TdR (percentage of the control rate measured in the absence of Tdr)1984Journal of medicinal chemistry, Aug, Volume: 27, Issue:8
A reappraisal of the effect upon thymidine kinase of thymidine derivatives carrying large groups at the 5'-position.
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.
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.
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.
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.
AID210870Thymidine kinase activity was measured by nonradiochemical assay method + TdR (percentage of the control rate measured in the presence of 5 uM Tdr)1984Journal of medicinal chemistry, Aug, Volume: 27, Issue:8
A reappraisal of the effect upon thymidine kinase of thymidine derivatives carrying large groups at the 5'-position.
AID1131507Antineoplastic activity against mouse L1210 cells at 400 uM1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
Synthesis and biological activity of several amino analogues of thymidine.
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.
AID210904Inhibitory activity against thymidine monophosphate kinase (TMPK) in Mycobacterium tuberculosis2003Bioorganic & medicinal chemistry letters, Sep-15, Volume: 13, Issue:18
Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID1145767Cytotoxicity against mouse Sarcoma 180 cells assessed as cell viability at 400 uM after 18 to 24 hrs relative to control1976Journal of medicinal chemistry, Apr, Volume: 19, Issue:4
Synthesis and antiviral activity of 5- and 5'-substituted thymidine analogs.
AID1145765Antiviral activity against Herpes simplex virus 1 infected in African green monkey Vero cells assessed as viral titer at 400 uM after 40 hrs by plaque formation assay relative to control1976Journal of medicinal chemistry, Apr, Volume: 19, Issue:4
Synthesis and antiviral activity of 5- and 5'-substituted thymidine analogs.
AID210872Thymidine kinase activity was measured by radio chemical assay method1984Journal of medicinal chemistry, Aug, Volume: 27, Issue:8
A reappraisal of the effect upon thymidine kinase of thymidine derivatives carrying large groups at the 5'-position.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (35)

TimeframeStudies, This Drug (%)All Drugs %
pre-199025 (71.43)18.7374
1990's7 (20.00)18.2507
2000's3 (8.57)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.86%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other34 (97.14%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
5'-amino-5-iodo-2',5'-dideoxyuridine[no description available]medium40
uridine[no description available]medium30uridinesdrug metabolite;
fundamental metabolite;
human metabolite
deoxycytidine[no description available]medium30pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
deoxyuridine[no description available]medium40pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
3'-amino-2',3'-dideoxythymidine[no description available]medium70
5-amino-2'-deoxyuridine[no description available]medium20
n(3)-ethylthymidine[no description available]medium10
5-cyano-2'-deoxyuridine[no description available]medium10
stavudine[no description available]medium30dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
zidovudine[no description available]medium30azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
3'-azido-2',3'-dideoxyuridine[no description available]medium20
3'-azido-2',3'-dideoxy-5-bromouridine[no description available]medium20
3'-azido-2',3'-dideoxy-5-methylcytidine[no description available]medium20
2',3'-dideoxythymidine[no description available]medium40
2',3'-didehydro-2',3'-dideoxyuridine[no description available]medium20
2',3'-dideoxyuridine[no description available]medium20pyrimidine 2',3'-dideoxyribonucleoside
3'-amino-2',3'-dideoxyuridine[no description available]medium10
3'-azido-2',3'-dideoxycytidine[no description available]medium20
zalcitabine[no description available]medium10pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
2',3'-dideoxycytidinene[no description available]medium10
5-bromo-2',3'-dideoxyuridine[no description available]medium10
cytidine[no description available]medium10cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
ibacitabine[no description available]medium10pyrimidine 2'-deoxyribonucleoside
methylthymidine[no description available]medium10
5,6-dihydrothymidine[no description available]medium10pyrimidine 2'-deoxyribonucleosideMycoplasma genitalium metabolite
5-methyldeoxycytidine[no description available]medium102'-deoxycytidine
5-(1-propenyl)-2'-deoxyuridine[no description available]medium10
thymidine[no description available]medium210pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
trifluridine[no description available]medium20nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
EC 2.1.1.45 (thymidylate synthase) inhibitor
fluorodeoxyuridylate[no description available]medium10pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
5-fluorouridine[no description available]medium10organofluorine compound;
uridines		mutagen
thymidine monophosphate[no description available]medium10thymidine 5'-monophosphatefundamental metabolite
doxifluridine[no description available]medium10organofluorine compound;
pyrimidine 5'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
prodrug
alovudine[no description available]medium10pyrimidine 2',3'-dideoxyribonucleoside
thymine arabinoside[no description available]medium10N-glycosyl compound
2'-deoxyuridylic acid[no description available]medium10deoxyuridine phosphate;
pyrimidine 2'-deoxyribonucleoside 5'-monophosphate		Escherichia coli metabolite;
metabolite;
mouse metabolite
3'-azido-3'-deoxythymidine 5'phosphate[no description available]medium10
edoxudin[no description available]medium10pyrimidine 2'-deoxyribonucleoside
bromodeoxyuridylate[no description available]medium10
2'-fluorothymidine[no description available]medium10
3'-amino-3'-deoxythymidine 5'-monophosphate[no description available]medium10
5-iodo-2'-deoxyuridine 5'-monophosphate[no description available]medium10
4'-thiothymidine[no description available]medium10
bromodeoxyuridine[no description available]medium10pyrimidine 2'-deoxyribonucleosideantimetabolite;
antineoplastic agent
idoxuridine[no description available]medium110organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
vidarabine[no description available]medium10beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic
acyclovir[no description available]medium102-aminopurines;
oxopurine		antimetabolite;
antiviral drug
cytarabine[no description available]medium10beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
ribavirin[no description available]medium101-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
brivudine[no description available]medium10
fiacitabine[no description available]medium10
thymidine 5'-triphosphate[no description available]medium40pyrimidine 2'-deoxyribonucleoside 5'-triphosphate;
thymidine phosphate		Escherichia coli metabolite;
mouse metabolite
sodium bicarbonate[no description available]medium10one-carbon compound;
organic sodium salt		antacid;
food anticaking agent
3-aminobenzamide[no description available]medium10benzamides;
substituted aniline		EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
5-chloro-2'-deoxyuridine[no description available]medium10
phenyl isocyanate[no description available]medium10benzenes;
isocyanates		allergen;
hapten
cyanates[no description available]medium20
methotrexate[no description available]medium10dicarboxylic acid;
monocarboxylic acid amide;
pteridines		abortifacient;
antimetabolite;
antineoplastic agent;
antirheumatic drug;
dermatologic drug;
DNA synthesis inhibitor;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
immunosuppressive agent
2-chloroethyl isocyanate[no description available]medium10
ConditionIndicatedRelationship StrengthStudiesTrials
Bladder Cancer0low30
Bladder Neoplasms0low30
Bladder Tumors0low30
Cancer of Bladder0low30
Cancer of Colon0low10
Cancer of Skin0low10
Cancer of the Bladder0low30
Cancer of the Colon0low10
Cancer of the Skin0low10
Carcinoma, Ehrlich Tumor0low10
Cell Transformation, Neoplastic0low10
Colon Cancer0low10
Colon Neoplasms0low10
Colonic Cancer0low10
Colonic Neoplasms0low10
Delayed Hypersensitivity0low10
Ehrlich Ascites Tumor0low10
Furrow Keratitis0low10
Herpes Simplex0low10
Herpes Simplex Virus Infection0low10
HIV0low10
Hypersensitivity, Delayed0low10
Hypersensitivity, Tuberculin-Type0low10
Hypersensitivity, Type IV0low10
Keratitis, Dendritic0low10
Keratitis, Furrow0low10
Leukemia L 12100low30
Leukemia L12100low30
Malignant Tumor of Urinary Bladder0low30
Neoplasms, Bladder0low30
Neoplasms, Colonic0low10
Neoplasms, Skin0low10
Neoplastic Cell Transformation0low10
Neoplastic Transformation, Cell0low10
Sarcoma 1800low20
Sarcoma 180, Crocker0low20
Skin Cancer0low10
Skin Neoplasms0low10
Transformation, Neoplastic Cell0low10
Tuberculin-Type Hypersensitivity0low10
Tumorigenic Transformation0low10
Type IV Hypersensitivity0low10
Urinary Bladder Cancer0low30
Urinary Bladder Neoplasms0low30

Research Highlights

Safety/Toxicity (1)

ArticleYear
Modulation of the metabolism and cytotoxicity of iododeoxyuridine by 5'-amino-5'-deoxythymidine.
Molecular pharmacology, Volume: 23, Issue: 3		1983
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]